Dressing and Shopping for a Life in Flux

I’m currently going through a period of transition in my life.  My personal styling business is winding down and I’m not sure what’s next in terms of my career.  I’m also working to cultivate new hobbies and interests, which I hope will also lead to new connections and friendships.  At present, I don’t go out much and when I do, my outings are mostly quite casual in nature. The majority of my time is spent at home with my husband and two cats, and I spend many of my days in workout clothes and lounge wear.

Transition and Our Wardrobes

While all of this transition has been going on, I’ve also been working on paring down my oversize wardrobe to a more manageable level.  However, as I’m not sure what’s next for me in my life and what clothing I’ll need for my personal and professional activities, it’s been difficult to decide what to keep and what to purge from my closet.  Since I know many of you have experienced or are currently going through similar challenges, I decided to address the issue of dressing and shopping for a life in flux.

Dressing During Times of Transition

Perhaps your transitions are different from mine.  Maybe you recently retired or have re-entered the work force after years of raising a family.  Or perhaps you’re moving from one career to another or are starting to date again after a recent divorce or break-up.  All of these changes can leave one feeling perplexed about closet and shopping needs.  I don’t have all of the answers, but hopefully I’ll be able to offer some helpful suggestions for you during your time of transition.   As always, I welcome your feedback and suggestions.  I’m sure many of you have “been there, done that” and can add a lot of value to the conversation!

When You Know What You’re Transitioning Into

When we’re in transition and know what we’re moving towards, it’s easier to know how to dress and shop. For example, if you are returning to a career in finance or law after a hiatus, you know you’ll likely be wearing suits and other formal business attire to work.  Or if you’re going back into the dating world, you’ll need a few dresses or some polished pants outfits for nights out on the town.

Even if you’re reasonably sure of the types of clothing you need, I caution you not to buy too many new things before you actually start your new job or begin going on dates.  Compile a few “go-to outfits” for interviews or dates and then see how things go.  You may find, for example, that you’d rather not dress so fancy during first dates or that suits aren’t really required for your interviews.  If so, you’ll be glad you didn’t spring for a whole new wardrobe that won’t end up meeting your needs.

Start in Your Closet

I recommend that you always start in your closet.  Many times we think we need to go out and buy a lot of new clothes when in fact we have most of the necessary “building blocks” within our own closets.  That’s what frustrates me so much about television shows like “What Not to Wear.”  The show hosts always throw away everything in the makeover subject’s wardrobe, when the person likely had some good pieces that could have been retained and later mixed in with her new purchases.

Whenever I did a “closet audit” with a wardrobe styling client, she was often pleasantly surprised by how much was kept (the final decision was always hers) and how few items were placed on her shopping list.  Many times, the client only needed a few new pieces (often accessories) to enhance her wardrobe to better meet her lifestyle needs.

During the closet audit, I’d also help the client to combine her current garments into new looks to either dress things up or down as needed.  For example, if a woman left a corporate job where suits were required, those suits could be broken up.  The suit jacket and skirt/pants could then be combined with more casual pieces to create business casual outfits to meet the client’s new needs as an entrepreneur or working in a more dressed down office setting.

When You Don’t Know What You’re Transitioning Into

The more difficult transition situation is when the person doesn’t know what he or she is moving towards.  That is my situation at present.  I am no longer meeting with clients or attending networking meetings and I’m not sure if I will be doing such activities again in the near future – or ever.  I have no idea what types of professional (or for that matter, personal) activities I’ll be doing even a few months from now.   That makes it much more difficult to manage my existing wardrobe or shop for any new pieces.

Transition or no transition, I’m committed to reaching my goal of having a smaller, more manageable wardrobe filled only with things I love and wear, so I continue to audit my closet on a regular basis. As I’ve been paring down my closet, here are the criteria I’ve been using to determine what should stay and what should go.  It’s still a work in progress, of course, but it’s going well so far.

  1. The Love Factor – As I go through my clothes, I ask myself if I love each item in question.  I rate each garment on a scale of 1-10 in terms of fit, style, color, and comfort.  Ideally, anything that’s rated under an “8” is slated for donation or consignment.  I may keep some wardrobe staples until replacements are found (pants come to mind here…), but ideally only “8”s or above get to stay in my closet.
  2. The Need Factor – Does the item in question meet a current lifestyle need?  Do I see myself wearing it within the next few weeks to an actual activity in my life?  While I’m maintaining a very small capsule for potential business needs (e.g. interviews, networking, speaking), the majority of my more formal pieces have been passed on.  I don’t see a real prospective need for such garments, so I’ve let them go.
  3. Review the Current Season – Since it’s summer in my part of the world, my primary focus has been on garments I will wear for that season.  While I regularly review my entire wardrobe for the “love factor” (my standards keep increasing, so I like to review my clothes fairly often), the “need factor” for fall/winter remains up in the air.  I’m keeping everything I love for the time being and will re-evaluate what I need next season when that time approaches.

How to Shop When You Are in Transition

In regards to shopping, we should proceed very carefully when we aren’t sure what’s next for our lives.  The way I’m approaching shopping now is to only buy items that I’ve determined will fill a current need or which will replace existing pieces that have worn out or need to be upgraded.   If I don’t think I’ll wear a prospective new piece within the next week or two, I won’t buy it!  That’s part of my reason for skipping the Nordstrom Anniversary Sale.  I have no idea what I will need or want to wear when fall weather arrives a few months from now.

I maintain a shopping list for items I need, and I edit this list frequently.  Since I’m still focused on decreasing the size of my wardrobe, I aim to buy very few new pieces that are high quality and which I can’t wait to wear.  For example, I bought a new Brighton handbag (one of my favorite brands) in June and have been carrying it daily since that time.  I’ve also purchased some upgraded loungewear and a casual jacket for my regular evening walks.  I know these new items will receive a lot of wear over the coming months, so they were good purchases.  They meet my current lifestyle needs and will ultimately have a low cost-per-wear.

The Bottom Line

While this post has been about dressing and shopping during times of flux, the basic principles apply to everyone. We should only buy – and keep – what we love and what works for our current bodies and lifestyles.  With very few exceptions, we should not buy or keep things for “just in case” scenarios.  If we don’t have an actual event to which we will wear an item in question, it should remain in the store instead of coming home with us. We shouldn’t buy something just because it’s “in” or because a salesperson told us it looked great on us.

If we shop for defined lifestyle needs and stay true to our personal style aesthetic, we’re much less likely to end up with “wardrobe benchwarmers.” And if we only keep clothing and accessories we actually wear, instead of being afraid to purge things because we might need them someday, our closets will be smaller and we’ll be happier.   This advice applies not only during times of transition, but all the time!


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Comments

  1. Great post Debbie! I just looked in my closet and I have three fancier dresses, two pairs of high heels, an evening bag, and a thick wool sweater that don’t get worn in my everyday life. So most of what I own are things that I wear. I cleaned my out my closet a couple of days ago (I’m not usually a numbers girl, but I thought of you and counted-53 items went). I still have a lot (too many) clothes and shoes, but I’m okay with that for now. I don’t feel that I am lacking anything and I feel like I have something to suit any occasion that comes up in my life. I will go through everything again in two or three months and see what isn’t being used.

    The shopping part is what is the transition in my life now. For years I have spend a great deal of time and money searching for great deals on more expensive clothing, much of it on Ebay. When I went up north to visit my family I spent about $200 on clothes. If I had stopped there it wouldn’t have been a big deal, but when I got home I kept looking online for more things to buy. I knew that I didn’t want to continue like that so I asked myself what was the thing I least wanted to give up. The answer to that was Ebay, so that is what went for the rest of this year. Online shopping in general has been where I have overspent and overshopped. Since I have stopped the online shopping I have found that so much time has opened up for me to do other things. I live over an hour from a mall and I haven’t found myself running out to TJ Maxx, Belk, and Kohls in town all the time, so I don’t think that shopping in person will be a regualr thing. When I do, I want to be very picky about what I bring into my closet.

    • Debbie Roes says:

      Sounds like you’re doing so well, Tonya! Congrats on your successful closet pare-down. 53 items is a lot to release (thanks for counting even though you’re not a “numbers girl”)! It seems like your wardrobe is in really good shape now. Mine is getting there gradually… What a great step you’ve taken by giving up Ebay for the rest of the year. I know that wasn’t easy for you to do, but it’s good that you know your weakness and are acting accordingly. I sometimes do too much online shopping, too. I have weaknesses both online and in-person. I haven’t bought much on Ebay (too worried about sizes), but nordstrom.com has gotten a lot of my business, as have a bunch of other sites! It’s good that you’re being more picky about what you bring into your closet. After doing Project 333, I can really see the value of a smaller, well-edited wardrobe!

  2. “If we shop for defined lifestyle needs and stay true to our personal style aesthetic, we’re much less likely to end up with “wardrobe benchwarmers.” -”

    This. I recently went through a massive closet audit and this one was profoundly different from all of the others before. I have had different transitions in my life that have, I thought, required different kinds of clothes and I’d modeled my shopping around that. And still kept ending up with a closet full of clothes and nothing to wear. This time, I thought long and hard before I even started building the donate pile. I asked myself what I wore most often, what were the items I just kept coming back to and then examined why. And I realized those clothes defined my personal aesthetic and were the things I felt best in because they were comfortable, flattering, fit well AND fit my aesthetic.

    I work in a professional environment but notwithstanding, I like to look a certain way. I like to dress up and even on the weekends, you will rarely see me in a pair of jeans. When I was unemployed for six months, I still dressed up almost everyday because that’s my thing– I like to dress up. I dress up to to go the grocery store. Figuring that out about myself was enormously helpful. I then felt free to get rid of all of my jeans except 1 pair for example (because when I rarely wore jeans THAT was the pair I grabbed). I was able to really get my closet down to what fit my lifestyle and aesthetic without that panic I would suffer previously at the thought of having too few options.

    • Debbie Roes says:

      Congrats on your successful closet audit, Marisa! How great that you took the time to ask yourself powerful questions to see what you were really wearing and what you really like to wear. Now you’re in a much better place as a result. Your story shows why lists of “must haves” don’t work in real life. Not every woman needs jeans, white button-down shirts, pencil skirts, and little black dresses. What we need is determined by our lifestyles and our personal preferences. There’s nothing wrong with preferring dressier clothing. I live in a very casual place and even though I probably don’t dress up as much as you do, I’m regularly asked why I’m so dressed up. I just smile and tell them I enjoy it 🙂

  3. Elizabeth says:

    My lifestyle is in transition, too, but there’s one constant — I love black cotton yoga pants. My strategy is to buy two new pairs per year. Knowing they will last at least three years each, my newest pairs become my “dressy” pants, my two-year old ones become my weekend wear, and my three-year-old ones become my gardening and workout wear. At the four-year mark, I turn them into rags or donate them. Because of this rotation, I always have a very black, new-looking pair for when I need to look good — although yes, my daughter has frequently reminded me, “Yoga pants are not real pants.” LOL!

    My husband employs the same strategy with his hiking boots. The new pair is for the workweek, the older pair is for the weekends, and the oldest pair is for yard work or fishing.

    Yoga pants and hiking boots — those are the constants in our lives. 😉

    • Grasshopper says:

      I do something similar with knit tops, jeans, and athletic shoes. The oldest ones are reserved for yard and house work. I have really worn out some pieces with this mindset and it feels really good to see a garment worn until it completely falls apart. It makes me feel like my money was well spent. I don’t feel so well about the items that are donated while still looking brand new.

    • Debbie Roes says:

      Elizabeth and Grasshopper, It sounds like you both have good strategies in place to get a lot of wear out of your clothes! I’m doing something similar with many of my tops (since I have so many!). I’ve relegated some previous favorites (that are a bit worn out) to at-home wear and for going on walks. Some of my lounge wear gets downgraded to workout wear, etc. It’s a good way to increase the wardrobe life cycle. Sadly, I still end up donating or consigning clothes that are in pristine shape because they weren’t a good buy in the first place, but I’m learning… At least those “mistakes” aren’t taking up space in my closet any more!

  4. Deborah (Deby) says:

    I think we are all in some kind of flux because you can never accurately predict what is going to happen in any given life or work situation. I have found that dressing for a life I imagine myself having is not always exactly the reality, so you have to be a bit flexible.

    (My advice when in transition: keep your receipts in case you have to return anything, and pay attention to need/love that Debbie speaks of. Its important.)

    My own recent story about flux: one year ago I was largely responsible for opening a new branch office for our company. During the time of renovating the space to suit our needs, my attire was very casual because I spent a lot of time with general contractors and I wanted them to feel comfortable around me. In business, I tend to dress for my audience so as to be able to communicate better. I figured that after the renovation was complete, once we opened for business that I would dress in a more professional way. With this in mind, I went out to purchase some new work clothes to fit my role I imagined at the new office.

    Dressing professionally is very different now than it was a few years ago. I have had the luxury, for many years, of working primarily from a home office, often attired in black leggings (my one wardrobe constant 3 seasons of the year) with a variety of long tops (also short dresses) to give a hip creative vibe as an expression of what I do career wise (graphic designer, marketing manager). Insulated at home much of the time, I imagined that people in offices dressed more “professionally” than myself.

    I was wrong. I quickly discovered that what I considered professional, everyone else in my office considered to be “overdressed” compared to them. On the other hand, I considered most of them to be unprofessional in their ill-matching and sometimes inaproriate attire, so now most employees wear company shirts every day with their choice of bottoms. While I don’t go to the office every day, when I do, I wear the company color to give a feeling of solidarity, even if I am not wearing a company logo shirt. Our company color, cobalt blue, is not a color I have in my personal wardrobe, but it coordinates with pieces that I have, and fortunately it looks good on me. I have a small selection of cobalt blue separates that I wear just on the days I go to the office.

    I ended up taking back all those business clothes that were too overdressed (that’s why I say keep your receipts!) and rethought my whole wardrobe. Around this time I also learned about Project 333 and Debbie’s blog, so this has been a great help to me in figuring out my new professional wardrobe! Now I am looking forward to doing the fall winter segment because its been such a learning experience!

    • Debbie Roes says:

      You raised some excellent points with your story, Deby. It’s always a good idea to save receipts and make note of store return policies! On and off, I’ve had a personal policy to return anything I hadn’t worn in a month. I think I’m going to make that more of a hard and fast rule. But of course, it’s better to just buy the right things in the first place, but you’re right in that we don’t always know. It sounds like you were able to get onto the right course with your professional wear and you’re doing great now. I’m sure that soon your fall/winter segment will be in excellent shape, too! I’ve been working on my summer clothing, as we have late summers where I live. I will likely send some more things out the door very soon. It feels great to pare down my wardrobe and it’s easier than I thought it would be since I did Project 333!

  5. Good post! I agree with you Deby and Debbie. I know that I will always be in flux and I want to stay in flux and maintain a small amount of clothes that I wear frequently.

    I no longer want to shop for and collect clothes I “might need” since I can never accurately predict the future. Back when I purchased for a work and social life I imagined myself having I always guessed wrong and the result was a closet full of great clothes I seldom wore.

    • Debbie Roes says:

      You and me both, Terra! I had SO many “just in case” clothes that just hung in my closet. Most are now gone (I shudder to think about the wasted dollars) and I am really trying to buy things I will wear pretty much right away. I am often drawn to dressier clothing but it just doesn’t have much of a place in my real life. I’d rather buy what I’ll actually wear and have my clothes be worn out when they end up leaving my closet!

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