Life’s Too Short to Settle and Wear Things Out of Guilt!

I’ll start this post off with a story.   Last night, my husband and I had a “date night” to see a movie (“The Disappearance of Eleanor Rigby,” which I really enjoyed).    I decided to wear a dress that I had purchased back in August and had worn once during September.   I didn’t try this dress on for the “first impression test” two weekends ago, as I had worn it so recently, but I really should have.

Settling and Feeling Guilty

Do you wear things you don’t love because you feel guilty?

The first time I wore the dress, I didn’t love it.   I partially chocked up those feelings to being bloated and hormonal, but I also I felt the dress was too voluminous.  So I did what I’ve often done in the past.  I brought it to my tailor to have it taken in.   After I picked it up, I tried it on to make sure the alteration had been done correctly.  It seemed fine, so I hung the dress back up in my closet.

Not Honoring the First Impression

Fast forward to last night…   I was getting ready to go to the movies and thought it would be a good time to wear the dress again.   I put it on and wasn’t thrilled with how I looked and felt in it, but I pushed myself to wear it anyway.  Instead of heeding reader Deby’s excellent advice about honoring my first impression, I wore the dress, mostly out of guilt and the feeling that I should give it a chance.   However, if I’m being completely honest, which I always try to be here, I was seriously worried that I had made two big mistakes, in buying the dress in the first place (yes, it was another consignment store purchase!) and in trying to rescue it through alterations.

The result was that I felt frumpy and unattractive the entire time I was out for a nice evening with my husband. What should have been a purely enjoyable outing was marred by my stubborn commitment to wearing a sub-standard dress!  I liked the rest of my ensemble – the jacket I topped the dress with, my shoes, and my jewelry.  But that stupid dress ruined the entire look and pretty much spoiled my evening!

When I got home, I tried swapping the dress out for a stand-by favorite – and I instantly felt much better.  I no longer felt like I had gained twenty pounds overnight and aged at least ten years.   I was struck by strong feelings of regret at not having changed into a more suitable dress before leaving the house.   Had I done so, I would have felt far more confident and attractive and would have had a much better time last night.   Needless to say (I hope, anyway), the dress is now in the consign/donate pile, but not without my having suffered through two evenings of feeling “less than” while wearing it.

I Know I’m Not Alone…

I shared this story because I know I’m not alone in this type of experience.  I’m sure many of you have gone through something similar.  We have things in our closets that we shouldn’t have bought but are unable to return for one reason or another.  Perhaps the return window has passed or maybe it was a final sale item bought on clearance or at a resale store.

We feel guilty for our purchasing mistake, so we force ourselves to hold on to the item.  In some cases, it hangs in our closet for months or even years with its tags still attached.  In other (and perhaps worse) instances, we force ourselves to wear the item, all the while internally kicking ourselves for the stupidity we exhibited by taking it home with us in the first place.

Metaphorically Flogging Ourselves

Why do we do this?  We do we insist on punishing ourselves and prolonging our self-effacing feelings?   Do we think that by continuing to metaphorically flog ourselves, we’ll teach ourselves a lesson or be able to do penance for our wrong deeds?   It may be one or both of those things or something else entirely, but I’m here to say that life is too short to settle for less and feel bad!

I’ve done that for far too many years and as I approach the big 5-0 (yes, it’s close to two years away, but it’s coming!), I’m ready to stop such nonsense now and forevermore.   Even if you’re in your twenties and are reading this, life is still too short to wear sub-standard clothing as a way of trying to un-do a purchasing mistake.  We just don’t need to do that anymore!

Wise Words from Bridgette

I had my follow-up Skype session with Bridgette Raes yesterday afternoon.  I’ll do a full de-brief on the session next week, but I want to share some words of wisdom that she imparted to me.   In preparation for our session, I sent her photos of some problematic outfits for which I wanted advice.  Some of those were outfits I’d actually worn, while others were ensembles I put together using either wardrobe “benchwarmers” or new pieces that I was unsure how to wear.   I also sent her photos of about twenty of my favorite outfits, looks in which I felt good about myself and true to my style.

Here’s what Bridgette had to say…  She told me that although she could help me style some of the tricky pieces I showed her, there was really no need to hold on to them.   She was very impressed with my “good outfits” and felt that I had more than enough pieces there to mix and match and create all of the looks I’d need for the various events in my life.  Her basic sentiment was,

Why try to force old, sub-standard, or no longer your style pieces to work when you already have so many good items in your closet?

She said that many of her clients have few or no garments that work and pretty much have to start from scratch, but that is not the case for me at all.   I have a lot of great items and should be wearing those all the time instead of pushing myself to wear other things out of guilt or obligation.

An “Aha Moment” and a Vow

After last night’s dress incident, Bridgette’s words came back to me and I had sort of an “aha moment.”  She is exactly right!   I could have worn one of my “9” or “10” outfits last night and felt fabulous, but instead I forced myself to don a mistake dress as a sort of penance for my shopping faux pas.   In a sense, I wasted a precious evening out with my wonderful husband when I could have felt amazing in one of my tried and true “winner” looks.   While I still managed to enjoy the movie and time with my husband, the whole experience could have been much better, if not for my stubborn nature!

So today I make a vow and I’m hoping some of you will join me in this commitment.  I vow to only wear things in which I feel attractive, comfortable, and true to my style.   If I try something on and my first impression is either “Yuck!” or “Ho-Hum,” I will take it off and change into something else in which I feel fabulous.   I will then pass the less-than item(s) on to someone else who may be able to enjoy them far more than I will.

If I can re-coup some of my money through consignment, great, but that won’t be my primary concern.  My first and foremost commitment is to enjoying my life.  So no matter how much money I spent on something, I won’t keep it if it’s uncomfortable, ill-fitting, frumpy, or in a style that doesn’t mesh with the aesthetic I want to present.

We Are Given No Guarantees

I’m sure this won’t always be easy.  There will still be pangs of guilt and feelings of remorse that will surface each time we opt to pass something on that is “still perfectly good” or for which we spent “good money.” But life isn’t just about saving money, getting a “great deal,” or mitigating our mistakes.

Life is to be enjoyed, cherished, and experienced.   After all, we are given no guarantees. While many of us will grace this earth for eighty, ninety, or even more years, some of us won’t be blessed with so much time.  I’m not assured that I will reach 49 and I’m definitely not promised decent health (I already struggle a lot there) with which to fully embrace my life.

I want to make the time I have count.  I don’t want to shop my life away and I’m working on developing new interests and coping mechanisms.   I also don’t want to “settle” and treat myself as anything less than the truly deserving being that I am.   I’d rather have just fifty pieces in my closet that I love and feel great in than 100 or 200 or more in which I feel old, fat, frumpy, or attractive.   Closet set point or no closet set point, I’m ready to pass along any and all garments that have me feeling the way I felt last night.

Please Hold Me to My Promise

As you can tell, I have very strong feelings about this.  I wanted to write this while my emotions were still heightened and my commitment was maximized.   I want you to remind me of what I wrote here if I should ever falter.   I want to be held to the promises I’ve made here today and I encourage you to make similar promises to yourselves, if you have not already done so.

I know some of you are farther along in the journey and have already learned these valuable lessons, and I applaud you for doing so.   Perhaps you can help the rest of us to stay strong should we ever lapse back into settling and allowing guilt to force us to hang on to our shopping mistakes.

We’re all in this together.  I value the support I’ve gotten from many of you and I feel so honored when I receive comments and emails that tell me my words have touched you and helped you in your journey to trade your full closet for a much fuller life.   I am truly blessed to be able to share my thoughts and experiences here and I am grateful for how much I’ve learned from all of you, too.

I’m going to keep on keeping on, day by day.   Some days are easier than others to be sure, but little by little, I’m growing, learning, and changing.  The light at the end of the tunnel has grown stronger for me and I hope it has for you, too.   We all deserve to have workable wardrobes that we love, as well as full, happy, and joyous lives.

65 thoughts on “Life’s Too Short to Settle and Wear Things Out of Guilt!

  1. Excellent post Debbie. I can identify with you. I have worn clothes I am not keen on or are not my style anymore and it does effect my confidence, it drags me down and makes me feel grumpy and mad at myself. It does ruin my day too. If I recognise in time I am unhappy in an ensemble I do try to change my clothes to an outfit I know works through many wears. Anything I am unsure of I try to wear around the house and if at any point I feel uncomfortable I can change into something else. Please don’t be too hard on yourself, you didn’t like or feel comfortable in the dress and as a result have chosen to donate/sell which is better than putting it back in the wardrobe and trying to ignore that it never happened.

    • Good suggestion to wear things we’re unsure about at home, Sharon. That way, it’s much easier to change if we end up feeling that something just doesn’t work. As for being hard on myself, I definitely can be, but I’m trying to learn from my mistakes instead of beat myself up for them. We can’t change the past, but we can vow to do better moving forward!

  2. This reminds me of a saying, you can’t hate your way to self love. I don’t know if it’s true for you, but for me I find now that many of the rules I made pertaining to shopping do more harm than good now. It was important to have them when I was paring down my closet and while I still had that super compulsive feeling toward shopping. Now I just want to wear what I feel like wearing and feel good in it. I feel like if I do any more than that I am giving clothing too much power.

    • I love that saying, Tonya. It’s SO true! I’ve been hating myself and beating myself up for so many years, as well as trying to make myself change by being a sort of drill sergeant. Like you, I’m finding that many of my old rules are no longer working for me. Perhaps they served a good purpose in the past, but I’m also ready to stop giving clothes so much power. As I’m becoming less compulsive about shopping, I want to wear what I love and place more focus on other areas of my life.

      • If your goal is to cross a river, you may build a raft. It’s a big river, so you take your time selecting the sturdiest logs and lashings. You bind them tightly. Perhaps you waterproof the wood. And then you cross.

        After you cross the river, do you carry the raft on your back? No. What was essential for one phase of your journey is not necessary for another.

        The raft is ideal for crossing the river. It is useful and has its time and place. It is cumbersome to use while traveling on foot. The rest of the journey requires different tools that suit its time and place.

      • I like this analogy, Amy. Thanks for sharing. I think that perhaps Tonya and I are ready for different tools.

      • The thought about all the rules and constructs no longer serving us on this leg of the style journey hits home for me, too. Indeed, it does give clothing more power of us, consuming our thoughts, all the planning, hunting. It’s tiring just to think about. Sure, a plan is wise to keep us on course, but micromanaging our every day of getting dressed is just. too. much. for me at this point.
        Letting go of the ‘almosts’ is still hard for me, but I’m getting better at it. I just had a not so great experience with selling a NWT maxi dress I’ve been carrying like a monkey on my back for over a year and a half now. I’m getting a terrible price on it but I came to realize, I just want to be DONE with it. Enough. Why am I giving it this power? Letting it take up my mental space.

      • Good to see you commenting today, Mo. I’m guessing you are now back home and are probably quite happy to be there. I feel very similar to you about the micromanagement of clothing and getting dressed being too much at this point. I think that for those of us (like you, Tonya, and me) that have been working hard on shopping wisely and cultivating a workable wardrobe, it’s natural to get to a point where we want to pull back a bit and focus on other things. Yes, the “almosts” can be the trickiest to deal with. If something is horrible, it’s pretty easy to let it go, but those things that come close to working are harder to release. Congrats on letting go of the maxi dress. It may sting for a bit to get a low price, but soon it will be out of your memory and no longer taking up that valuable mental space!

  3. This a great revelation, Debbie. I don’t keep anything I don’t love, no matter how much $$ I’ve got wrapped up in the garment. To me, hanging on to clothes that just don’t work it just a constant reminder that I goofed and wasted $$. Out they go!!It’s so much more pleasant to see a bunch of well-loved clothes in my closet. Life is too short to go out on a date with your husband (or anywhere!) without feeling like a million bucks. Looking forward to more on Bridget’s sage advice.

    • You’re absolutely right, Dottie. Hanging on to clothes that don’t work is a constant reminder of our mistakes and wasted dollars. Once the offending items are out of our closets, the guilt tends to fade away fairly quickly. I have lots more advice from Bridgette to share but it will take me a little while to put it together. Stay tuned!

  4. Oh my gosh! I had the same experience this evening… Went out to dinner with an old friend in a navy cotton sweater… Didn’t cost a lot, but I feel rather meh in it. It’s going in the bye bye pile! Nothing super wrong with it, but definitely nothing right either. I can and will do better!! Thanks for the reinforcements!!!

    • Congrats on throwing that sweater in the “bye bye pile,” Paula. It feels good, doesn’t it? I’m sure you have other sweaters in your closet in which you feel fabulous, not “meh.” Onward and upward!

  5. I usually give the item 2 tries, if it fails the second try, it is gone. Sometimes the first try is not because of the garment, but because of bloating or hormone issues or maybe I paired the item with the wrong shoes, blazer, pants etc.. Usually I know by the second failed wear or try on in the morning that the item just is wrong and needs to go! Also sometimes my husband likes to see me in certain outfits or items of clothing, so I would keep them for his benefit….well sorry honey not anymore, if I hate it, it has to go! I have far too much in my closet to keep anything that makes me feel yucky! Great post as usual Debbie 🙂

    • I usually proceed much like you do, Bella. But in the future, I’m going to take Sharon’s advice above to wear such items around the house for their second “test drive.” That way, it’s much easier to change if you feel blah or ho-hum after a short time period. My husband gets upset when I get rid of things sometimes, too, but I usually remind him that I have other items that both he and I love. He generally comes around at that point 🙂

  6. What a great post, Debbie! I’m so happy you’ve had this a-ha moment. It shows real progress. I’m struggling with something similar today. The shirt I’m wearing isn’t bad, but it’s not good enough. I’m trying to make it work because it’s a relatively recent purchase, but I think it’s time to cut my loses. I have plenty of other shirts that do work, so why bother with this one? I don’t need so-so clothing in my closet. Bridgette’s words of wisdom are just what I needed!

    • I’m glad this post hit home for you, Kayla. I knew I wasn’t alone in my experience. I think many of us try to make things work and sometimes we succeed. But if we have to try TOO hard, it’s probably time to let them go. Bridgette has lots of words of wisdom and it was interesting how quickly this one piece of advice became ultra-meaningful to me!

  7. I’m impressed with your insight Debbie. You’ve come a long way! I received news last night that a good friend (whom I’ve lost touch with since I moved away) lost her boyfriend of at least 6-7 years in a car accident. He was only 45. And my first husband died at 48 from leukemia. So you are absolutely correct that we should all live today like there’s no guarantee of tomorrow. We all need to give ourselves permission to wear what makes us happy even if that means culling expensive wardrobe mistakes. I need to remind myself of this too. Have a great weekend, my friend!

    • My condolences on the loss of your friend, Kim. I knew about your husband, but didn’t realize he was my age when he passed. We really do need to live today like there’s no guarantee of tomorrow, but most people don’t do that. I know it’s a balancing act between realizing we don’t have all the time in the world and obsessing about the potential of dying or losing a loved one. I haven’t been able to find that balance yet, but I keep working on it. Perhaps a good positive step for me and many others is to wear what makes us happy. That’s one small step that we can take toward embracing and enjoying the now.

  8. I used to do the same thing. I always tried to make a garment works because it was a gift / expensive / a great deal / I wasn’t wearing it often enough / any other reason.
    Since I pared down my wardrobe in August (more than 80 items left my closet! I wouldn’t have thought I had so much in my closet in the first place since I’ve never been a shopaholic or even a regular shopper), started The Project 333 and an outfit journal (thanks to your blog by the way), I’ve found that it’s no longer the case! As soon as I put something on, I immediately feel if it’s a good or a bad pick. And as a result, I feel much more comfortable with myself, I’m learning to love my body and how to valorize it.

    • Thanks so much for your comment, Cedrique. It sounds like you’ve made some amazing progress in recent months and I congratulate you! I’m happy that my outfit journal idea has been helpful to you along the way. I think it’s so great that you immediately know if something is a good or bad pick for you when you put it on. I hope to be in that same place before too long.

      Dottie, I hadn’t heard of the word “valorize,” either, but we both learned a great new word today 🙂

      • Haha! I guess it’s because I’m French, I sometimes use French words in an English way. I guess this time it was for the best!

      • I’d like to use some French words in an English way myself 🙂 I took French years ago and love the language, but I’m very rusty at this point (I guess I need to book a trip to your lovely country…). But I was happy to learn a new word!

  9. Very interesting subject indeed! I think most of us already felt this – forcing ourselves to wear or use an item because it was purchased, cost money and it still perfectly fine. In my case, this is something I have done a lot with my 2012-2013 purchase mistakes ie those I made after I started editing my closet and refining my style. Because these were the most recent purchases, because I spent quite some money on them, but also because discarding them would have been admitting my failure, and therefore admitting my setback in my simplification journey (whereas I got rid of the “before the first editing” items without any guilt because they were purchased by the “old” me).

    However I agree with you (and Bridgette) that there is no reason to torture ourselves by wearing something that isn’t working out. We already wasted money on it, no reason to waste time and closet space any longer.

    The strategy I adopted with these now is to learn something from these mistakes and think about them when I’m about to buy something new. So I assess this “mistake” this way:

    – Why doesn’t it fit? Can I try and find outfits that make it work? Maybe it’s just a question of proportions or colour associations. –> Usually this makes me either find new outfits and turn a meh item into a keeper, or it makes me understand some style details, and why this item didn’t work.

    – Why and it what circumstances did I buy it in the first place? Was I trying to emulate a silhouette I saw on soomeone else? Was I upset? Were there some sales? –> this helps me understand why the purchase mistake happened in the first place to avoid doing it again

    – And at the end, I remind myself of these learnings (about my style and shopping habits), so that next time I’m about to buy something, I can realize in time that it’s about to be a shopping mistake.

    Also, taking away learnings from such a mistake helps feeling less guilt about removing it from my life – OK I wasted the money but at least I learned something about my style and shopping habits. I won’t fall into the same trap a second time.

    I hope that’s clear and it helps 🙂 Thanks for keeping writing such honest posts, it’s very refreshing to see a blogger’s “behind the scenes”, and not only a perfect image without the struggles.

    • Hi Kali!

      Thank you for reminding me that even after we think we’ve learned better, it’s still possible to repeat our buying mistakes. A recent fall closet overhaul has made an already small wardrobe uncomfortably pinched, and I’m struggling.

      Your comment about the circumstances surrounding a purchase (and the times it’s been worn) are so true! I’ve ditched a “perfectly good” suit that was shrouded in defeat. A recent sweater purchase is already on the donate pile: a casualty of FOMO on the Everlane bandwagon. What’s also hard for me recently is trying to assess items through an increasingly older lens: don’t want to look frumpy but don’t want to do the dreaded “mutton like lamb” look, either.

      The insights and honesty that you and Debbie offer in your respective blogs are so encouraging and helpful. Thanks to you both!

      • I have the same problem about getting older, Amy, although I’m likely older than you are. I’ve gotten away with dressing in some younger styles for a long time because people always think I’m younger than I am. Now I feel caught between too young and too old in how I dress and am often unsure how to appropriately strike a balance. Frumpy is like a four-letter word, but “mutton dressed as lamb” is not good, either. I suspect we’ll find our way eventually. I love Kali’s blog, too, and always enjoy her posts. I also enjoy when she comments here, too.

    • Thanks so much for your input, Kali. I think the part about admitting failure is often true for me, too, especially for my more recent purchases. Since I share everything I bring in and let go of here on the blog, it’s all very transparent. I sometimes feel as if I have the proverbial “egg on the face” when I make the same stupid mistakes over and over again. I think I should know better by now!

      But you are right that we should focus most of our attention on learning from our mistakes, and the questions you pose are very helpful. As for my mistake dress, I loved the print and it was being sold for a low price. I was also feeling excited about wearing dresses more often this summer and fell into the trap of thinking I needed to have A LOT of dresses instead of wearing what I have more often. I’m still not used to repeating things so often, but in truth, I’m NOT really re-wearing my items all that regularly.

      As for my honestly, I really don’t want to be any other way. There are far too many bloggers out there presenting a face of perfection, but I know it’s not real. I want to be real here, not only because it is refreshing and helpful for readers, but also because it moves me forward in my recovery. As the old saying goes, “The truth shall set you free.” Little by little, that’s what’s happening for me.

  10. I love your vow and plan to do the same Debbie!! I’ve worn things I didn’t like as well and know how it can add a bad vibe to an otherwise good day. I have been doing this recently with a burgundy blouse I bought- it’s perfectly lovely and a great color but I feel bloated and uncomfortable when I wear it. I will purge it tonight!!! It’s sad because it is a recent purchase and I have such few tops. I’ll have to get a replacement one day but not anytime soon- I’ve not shopped since Sept 10th so one month today!

    • Your burgundy blouse sounds like my dress, Meli. No need for either of us to feel bloated and uncomfortable in our clothes! I’m so glad you’re joining me in my vow. My dress was a very recent purchase, too, but I’m going to cut my losses and move on. I don’t really need to replace it in the near term, as I have a number of other dresses that work much better. Congrats on not shopping for a whole month! I hope it’s feeling easier for you than it has in the past. Part of how I’ll know I’ve come close to recovery will be when I don’t shop for a month or more, not because I’m forcing myself not to but because I didn’t WANT to! That may be a ways off, but I know I’ll get there.

      • Thanks Debbie!! The urge to shop has really abated for me- for the first time I’m not white knuckling through this! I feel content and like my closet is more than ‘enough’ which is unusual when I consider I just did a 34 item purge! This month I have purged 3 items so far which is reasonable. I may do a quick first impression test on what is left though and see how I do.

      • Such excellent news, Meli! It’s so much nicer not to have that “white knuckling” feeling, isn’t it? Congrats on being able to purge so much without feeling the need to run out to the stores (or click that “buy now” button). Keep up the great work – you’re progressing fabulously!

  11. Last night I had an epiphany regarding my winter wardrobe. Because our climate here is wildly different in winter and summer, having two separate seasonal wardrobes is pretty much a necessity. I only have about a dozen pieces that can be worn the entire year. For me, summer clothes are more fun, relaxed and varied, whereas winter clothes are for staying warm and dry yet fashionable. The color palettes are different yet related, with summer being brighter and winter being muted or deep versions of the same colors.

    My thought process started last night as I was planning what to wear for work today, reviewing the day ahead to come up with an interesting outfit that would serve all my activities: working at my desk, walking the dog, lunch with a friend, quick tidying up of the house for expected weekend guest, and dinner with said weekend guest. Today is also a rainy day, so I need to dress to be able to spend time outside with the dog. Because of time constraints, I tend to move seamlessly (fashion word, lol!) from one activity to the next throughout the day without changing my attire. As I strive to come up with outfits that cover all activities, I tend to focus most of the interesting part of my outfit above the waist, with my bottom half being more utilitarian.

    This past week was really jam packed with work activities, luncheons, a day trip for work, as well as my home activities. As I mentally reviewed what I wore this week, I realized I was basically wearing the same thing every day, in different iterations. In other words, I have developed a fashionable yet practical winter “uniform” born of the convenience of running my life. And since it’s now coordinated and works together– I don’t really need to think about it so much–just WEAR it.

    What is my uniform? For starters, I wear skinny pants (usually corduroy, sometimes denim) or leggings (in various fabrications) nearly every day in winter. I’m slender on the bottom and like the fit, comfort and ease of movement of skinny pants. Over these, I layer tunics, pullover sweaters or long shirts, which I own in enough styles and colors so they don’t all look the same. Over that I layer a cardigan if needed, and I have those in a variety of colors and styles. I experiment with different combinations of lengths of tops and cardigans to give a layered look. I can create a number of different looks from casual to dressy, amping it with accessories that have a unique handmade look.

    For my feet, I assess the weather–knowing I will be outside tromping through the park. If its raining, black Crocs. If its dry, Birkenstock Arizona sandals. Both with wool socks. If its really cold, I wear Uggs with wool socks. If I’m getting dressed up, I usually wear flats with thin socks or opaque hose (and then my feet are always cold!), although I did purchase my first pair of heels in over 6 years a few weeks ago!

    I realized that while I have a few dresses and skirts–I don’t wear them often because my legs get cold, and I don’t like to wear opaque tights because they make my feet feel cramped in shoes. Last year I played around with wearing thin leggings under skirts with boots, and thats kind of an OK look that is being touted this season as “skeggings”. I’m still on the fence about this look.

    So now I am thinking about purging through my skirts and dresses to assess whether I am really going to wear them or if they are just hanging there for “some day”. I could get by with fewer of these pieces to cover my work needs. Most of my social events don’t call for skirts and dresses anyway.

    • I forgot to mention that I wear other types of boots besides uggs–I really like the look of boots in th winter!

    • Thanks for sharing your winter wardrobe epiphany, Deby. Hard to believe you’re already in winter wear when I’m still in tank tops here. But I guess my part of the world is a bit weird. Your winter wardrobe sounds great and like it truly suits your needs. You have a lot of varied activities, so it’s a bit of a tall order to have outfits that work for everything you do in a given day. But you’ve found a way to make it work and I applaud you! Good luck with going through your skirts and dresses and assessing them. I think I will find some more pieces to let go of soon, as it’s feeling easier for me to get by with less these days. I don’t do nearly as much as you do and 132 standard garments is very likely still too many for my needs.

      • I sent one knit dress (burgundy with a darker burgundy damask jacquard pattern) and a dark burgundy pencil skirt to consignment (the seams were annoying and the hem hit at the wrong spot), both of which didn’t coordinate well enough with anything else. My benchmark for matching is to make sure my separates coordinate in natural light, and then they seem to be OK in other types of lighting for the most part, with a few exceptions. The blue-to-green tones seem to be the most problematic when trying to assess under artificial light.

      • Interesting observation about colors and lighting, Deby. I find that when I shop, I often think the colors look different once I get them out of the store (and its fluorescent lighting) and home (with more natural lighting). Sometimes I end up returning things for that reason. Colors look a lot different on my monitor than at home, too, which throws a monkey wrench into online shopping. Congrats on finding two items to send to consignment. It’s better to get those pieces that aren’t working out of our closets!

  12. My clothing journal has really helped me identify these blah outfits. I have one column entitled, “What would I do differently.” Sometimes it is just one element of an outfit that needs tweaked. For example, I have a dress with a wide, rather low boat neck. I feel so exposed in it. I figured out I need to wear a jacket, cardi, or scarf with it. Then the dress looks great.

    In the morning I have noted in my journal that something is wrong with an outfit and gone home at lunch and changed! Once I identified what was wrong, I could barely stand to keep it on. It was as if what was wrong got “louder and louder.” I couldn’t wait to take it off. The worst, unfixable offenders went right to the donate pile!

    • I just added the “What would I do differently” section, too, Anne. I often used to touch on that before, but it’s helpful to actually have to ask myself that question every day. Some days, the answer will likely be “nothing,” but that hasn’t happened thus far. I’m learning a lot, though, through addressing that question. I get what you wrote about the wrong things getting louder and louder. I couldn’t wait to take that dress off the other night!

  13. I used to do this all the time! Over the years, I’ve slowly gotten better. This fall, I wiped my slate clean when I decided to do Project 333. Any piece of clothing I didn’t love went into the donate pile. I cannot describe the weight off my chest and the freedom I feel every day now when I get dressed. I get to love my outfit every single day!

    • Great to see you commenting here, Kayla! I think it’s wonderful that you’ve taken on Project 333. It was very helpful for me and it sounds like it’s having a positive effect on you, too. How great that you love your outfits each and every day now!

    • I did ask myself that, frugalscholar, and that’s part of why I swapped the dress out for another one after I got home. If it was just hormones, bad body image, a bad hair day, or a low mood (all of which are often issues for me), the switch would have made little difference. But it truly felt like night and day and that tipped me off to the dress being the problem (which I suspected all al0ng). My husband did think I looked good, but that wonderful man even loves how I look when I wake up in the morning. He’s definitely a keeper 🙂

  14. I spend time planning out how many pieces I want to have in my wardrobe, and getting tangled up in deciding if I want X number of short sleeved tops, or X+6, or X/4, and yet I bet if I just permitted myself to wear only my favorites, I could save myself a lot of angst. As we purge and purge, and plan our shopping, it all seems so daunting. And yet, the women that have “made it” to the goal of a small, well curated wardrobe don’t seem to have all this angst and planning frenzy. I have long wondered if they just get to a point where they don’t give a fig about other people’s opinions on them rewearing favorite outfits, and equally don’t feel remorse about past shopping mistakes that they somehow need to hang on to just because they spent money on it or some other reason. I suspect you’re at that point now, Debbie. Great work, and awesome realizations!

    • I really resonate with your comment, Sarah. I’ve mostly been just wearing my favorites in recent months and that’s been working very well for me. But then I did my “benchwarmer” update and started to panic a bit. I don’t want to let myself and others down by ending the year with a bunch of benchwarmers. However, if I just kept on doing what I was doing, it would have worked out as it’s supposed to, anyway. I would see that I don’t reach for certain things and I would then let them go. I often make things a lot harder than they need to be! I am getting to the place that you mentioned toward the end of your comment. I would much rather re-wear a favorite outfit and have a much smaller wardrobe than waste more special (or even ordinary) days and nights wearing something I feel unattractive and frumpy in!

  15. I am on a short trip away and had a revelation tonight after dinner in a restaurant. It was a tiring day, my room wasn’t right and I was famished and and exhuasted when walking into the restaurant. I ordered in a daze and got too much food, none of which was spectacular. I brought some leftovers back with me and consumed some after a couple of hours of napping. And guess what? Still pretty much the same mehness. So I am throwing away the rest of the leftovers, and I feel no guilt. Why would I? I made an error in judgment when ordering. I hate to waste money, and I spent as much on this dinner as I’ve spent on a nice sweater, so I do feel a bit of remorse that I didn’t enjoy it more than I did. But I am somehow able to give up on the dinner more readily than I would a sweater. I am really pondering this. Next time I have second thoughts on getting rid of a meh piece of clothing, I will think of it as a mediocre dinner choise. I don’t drag that out for months, why should I drag out ridding myself of an article of clothing?

    • This is a great story, Holly, and a wonderful analogy. I think a lot of people feel compelled to eat leftovers or finish a ho-hum restaurant meal just as many of us feel we should hold on to sub-standard clothing pieces. We worry so much about wasting money or having to acknowledge that we made an error. You’re right, though, that the clothing is harder to let go of. For one thing, it doesn’t spoil, so we have more time to second-guess ourselves. I know I feel bad about throwing food away, but I feel worse about getting rid of clothes I don’t love. At least in the latter case, someone else has the potential of enjoying it (which isn’t usually true in the case of the food). I will keep your analogy in mind when I deal with mediocre clothing moving forward. I’m sure I won’t have to wait too long, as I suspect there are still some “duds” in my closet. Good for you for throwing those leftovers away today!

      • Debbie, you’ve given me more to think about. In this case my hand was forced by not having a fridge in my room in which to store the food (that’s the room error I mentioned) and so I really had no choice but to toss it. You are so right that if I had a fridge I might have tried to save the food and salvage part of it for eating today. So maybe the lesson here is around choice. I had no choice but to toss the food and that is why I felt bad, but not full or remorse. I just tossed it and moved on. I will reemember this bit about choice with my closet too, as I really shouldn’t have any choice with some pieces but to let them go. They are just going stale in my closet. They will never be better, or change to a different color (now that I’m following my color palette I see clearly where my mistakes tend to fall on that spectrum) and I should not give myself a choice but to put them into consignment or the donation bag.

      • You talking about your hand being forced by not having a refrigerator in your room makes me think about when people have to downsize because they’re moving into a smaller space. A little over 4 years ago, my husband and I moved, plus we got rid of our storage unit. We were both forced to get rid of a lot of things, including clothing pieces. It helped a lot to have the impetus of the move to push us to let things go. Many times, people just keep EVERYTHING simply because they have the space. Yet they don’t realize the emotional burden this can sometimes create. It’s not nearly as easy to let things go without something (or someone) pushing us to do so, but it’s often a lot more rewarding. You seem to be on a good track. Paring down my color palette was an important step in my journey and made it easier for me to let things go. It may take a little while, but it will likely have the same effect on you. Best of luck to you!

  16. Hi Debby. Identifying what doesn’t suit you is as important and identifying what does, so these items have done their job in the insight they have given you. Often I see a look I like but when I try to recreate it it just doesn’t work. Models are tall, straight and slim and I am short and pear shaped. I try to analyse why something doesn’t work, following your example, and am getting a better idea of what not to buy, and what I will really wear . Over the summer I bought more than planned as I refreshed my wardrobe with things that I really like to wear. My next goal is to limit how often I feel the need to refresh my wardrobe and experiment with new looks, and what I need to buy to do this.

    • You’re definitely right, Lynn. It reminds me of the saying about people coming into our lives for a reason, a season, or a lifetime. Perhaps it’s the same with clothes, although it’s too much to expect we’ll have any clothes for our entire lives. Some of these “mistake” items were there for a reason, to teach us some powerful lessons. It can be difficult to decide what to buy when the bodies we see the clothes on are different from ours. It’s hard for me and I am at least tall even if I’m not model thin. Often we just won’t know until we try something on. It sounds like you’re making really good progress with your wardrobe. I am in much the same place. I want to stop buying so much and start being much more strategic about what I add to my closet.

    • I loved that post, too, Meli. No problem about sharing it here. It’s possible I may add it to my next “useful links” round-up anyway. It’s hard to choose from among Grechen’s posts, as they are all so good! That one in particular really resonated with me and I may opt to explore the topic myself in a future post.

  17. Thank you for this post, which has given me the permission I need to complete my closet purge and re-organization between now and Tuesday. I have taken two days of vacation to get this done, as it is suddenly cooler in my area and all of my clothes are still hanging on the back of doors, or piled on my guest room bed. I have been so “stuck” on this project since mid-summer, trying things on and then putting them in a “maybe” pile to be re-evaluated later, since I found it impossible to justify getting rid of them, for all the reasons you articulated so clearly. The “altered but still unwearable” pieces are the worst – it’s like throwing good money after bad and I just keep doing it. Amy’s raft analogy really resonated with me, and it’s going to be on my mind as I re-evaluate each piece of my wardrobe. “What was essential for one phase of your journey is not necessary for another” – BRILLIANT! What a great mantra to keep in mind when evaluating whether a particular garment should still have a place in your life or closet!

    • How wonderful that you have taken two days off to do your closet purge, TexasAggieMom! I’m glad my post was both timely and helpful for you. I loved Amy’s raft analogy, too. It was so wise and insightful and I’m sure it resonated with many. Best of luck with completing your project. Please let us know how it goes. I know you will feel a lot better once you get some of those not good enough items out of your closet!

  18. This blog article on a tiny closet is inspiring:

    This is the best line from the article to help me when choosing the things that I really love:
    ” Note: If you hesitate over an item, for even a second, you don’t love it.” So true. If I even hesitate a little bit, it means there is something I would rather wear. It’s difficult to accept that I have too many items in my closet that I hesitate over. Moving theses items into another closet so they are out of my sight helps with the final step of giving them away.

    • You are the Link Queen, Leah! You always share the best articles and videos. I think that link about hesitation is really true. I second-guess myself a lot because I tend to be fickle about what I like, plus I fluctuate in weight a bit (not enough to wear a bigger size but enough to affect how I feel about certain clothes), but deep down I know what works and what doesn’t. Moving the “maybes” to another closet is a good way to allow ourselves some buffer zone. If we don’t reach for those items (which I sometimes do but not often) after a month or two, it’s time to pass them on!

      • Sorry if I share too many links :). I know you have said that you are an information junkie and I am too. I get just as much reward from finding a halfway interesting article as I do from buying something. Sometimes I probably shop because there is nothing interesting to read. (One reason you need to keep writing!!) I fluctuate in weight too. Up and down about 7 pounds a few times a year. I’m a teacher and it has everything to do with stress (more stress, more weight – usually unless the stress is really high like now). I cleaned out my closet when I was about 5 pounds heavier and now I am going through a few removed items to see if they will work now that I weigh less. I do think that small hesitation is telling and I should pay more attention to it.

      • I don’t think you share too many links at all. In fact, they’re all very helpful and I’m sure others like them, too! I get a lot of reward from finding useful information, too, but I don’t know if that has ever stopped me from shopping. It would be nice, though! I think I probably gain and lose 5-7 pounds once or twice per year, too. It’s not that much for my height, but enough to make pants pretty uncomfortable sometimes, especially since any excess weight seems to make a beeline for my back side (not LOL). I hesitate to get rid of pants that don’t fit me well at the higher end of my range (where I am now, sadly), but I did put them on notice, so to speak. When my weight goes down (which is getting harder at my age), I will see if there is a still a place for those pants in my wardrobe. I’m guessing the answer will be no!

      • That’s why I like dresses. Pants are way less forgiving. I shop online at night after finishing school work (hmmmm…connection maybe) so if I find something interesting to read, that is a reward and I don’t find myself shopping. I will probably not look at online stores tonight because you have a new post ;).

  19. So many great comments here, Debbie! If nothing else, the robust discussion after each of your posts should assure you that you are in good company with your wardrobe struggles. I tackled some major closet donate piles this weekend (about 30 “real” items, plus a more streamlined winter accessory basket and undies drawer), and then I pulled my “not part of capsule wardrobe stuff out” and I put everything I didn’t really want to wear but was having trouble donating into two “purgatory” bins with the month and year. Over the next year, I can pull anything out if I want to wear it, but anything that’s still there in October 2015 will go. Those bins? Full of items that are just like the dress you wrote about in this post. Sometimes there is nothing wrong with the item – and nothing wrong with my body – but they don’t work well together. Better to pass them along so someone else can use them. There are probably 50-75 items between the two bins! I made a third bin for things that I love but which don’t work right now (I’m within a few pounds of wearing it or it’s for the wrong season), and it’s only half full. The rest of the stuff is in my closet. I may edit a little as I go along in there, too, as it leaves my closet a bit more full than I’d like. But it’s really great to feel like my wardrobe is getting closer to the “bests” and I can feel myself getting better at demanding things that feel good and meet my needs. It will mean a little shopping (part of putting things in purgatory is sometimes acknowledging that I need to spend good money to replace staples that are simply too worn).

    As always, glad to be on the road with you!

    • I do know I’m not alone with my wardrobe struggles, Rebecca. I knew that before I started the blog, but I didn’t realize as many women struggle in similar ways. I don’t know if I want to say that’s comforting, as I don’t wish such issues on anyone, but I do feel less alone through blogging and interacting with all of you. I sounds like you have a good system for paring down your wardrobe. I think the idea of “purgatory” bins could be helpful for those who have trouble deciding what should stay and what should go. I am not quite that organized with it, but I do often place items at the end of the closet rod or in another closet to designate them as things that may be on their way out. More often than not, these things end up going, but not always right away. Sometimes things that need to be replaced go in those area and I have about 5 such things right now. I need to make replacements a priority (and I am), as I always feel lousy when I wear things that are worn out and past their prime. You have done a lot of hard work on your wardrobe and it seems like it’s really starting to pay off!

  20. Debbie, you are a true star and so generous in how you share your experiences in a way that helps others on their own journeys. What I love about clients like you is you are active in the process. There is only so much I can do. What is the saying? “You can lead a horse to water…” I love when clients are ready to not only let go but do things differently.
    And, funny story, this weekend my husband and I were going through the closet to change it over to fall and he went through his ties. He has to wear one to work everyday so he has a lot of them. Some of them were over 10 years old but he has held on to them even though he didn’t wear them. A lot of it had to do with guilt or not feeling like he could get rid of them. We’re not Rockefellers, so there is also often this feeling like we need to hold onto something due to a scarcity mentality. Afterwards he said to me, “It just felt so good to say, ‘I never liked this tie. I am getting rid of it’.”

    We truly can’t let better in until we have the faith to believe that we deserve better. Clearing clutter, or getting rid of things that don’t serve us, isn’t just a physical removal of stuff, it is a mental one too.
    Keep up the good work. It has been nothing but a pleasure to see you through this journey.

    • How great to see you comment here, Bridgette. Thank you so much for all of your kind words! My time with you (as well as reading all of your great blog posts) has been instrumental in my style and wardrobe growth and transformation. But I had to be ready to make the changes and take in the suggestions. I don’t know if I would have been in the right place a year ago.

      I love the story about your husband and his ties. Lots of things are “perfectly good” but aren’t right for us. I think many people have that type of scarcity mentality that has them hold on to such items. I think that if I went into my closet even now, there would be some of those, “I never really liked this,” types of items. I didn’t believe I deserved better because I made the mistake of making wrong purchases. But at some point, we have to stop flogging and punishing ourselves! Your comment that my “good outfits” were more than enough for my life really struck a chord with me. It may still be a gradual process to let go of some of the other things, but I’m making good progress. Thanks so much for all of your help and encouragement!

  21. I think this is such a common problem. I know for me at least, it is something I struggle with a lot. The thought of wasted money is very frustrating, but it’s not always easy to forsee that this is what will happen when purchasing a new item. So far, the best I can come up with is to try and remember what has happened in the past to these questionable yet purchased items. At least doing so makes me pause longer than I would have previously when I shop.

    • It’s definitely a challenge to be able to foresee which items will be losers vs. winners. I look back at my accountability updates and why I bought things, and I seemed so confident about the items at the time. My outfit journal is helping me to better understand what works and doesn’t work for me, as is my documentation of why I get rid of things, but I’m still making mistakes! Hopefully, our mistakes will become fewer and farther between as we continue to learn valuable lessons.

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