Style Reflections – Summer Outfits Then and Now

Now that summer is well under way, I wanted to reflect on how my warm weather style has changed since I started this blog two and a half years ago.  I took some time to go through my outfit photos from 2013, 2014, and this year.   I selected some ensembles that were fairly representative of what I used to wear, as well as a group of looks that fit my current style quite well.

In today’s post, I share eight looks from the past two years, as well as eight looks from 2015.   I highlight what I no longer like from the previous outfits and what makes me happy about the current ensembles.   I also reflect a bit on what I would change about the older looks to make them work for me today.

Cabrillo National Monument

It’s summer – what have you been wearing?  (photo: Cabrillo National Monument) 

Summer Outfits from Yesteryear

Before I show you the outfits I have selected from 2013 and 2014, I want to say a few things.  The looks that I have selected are ones that I liked at the time.  While I may not love them today, I was happy with these ensembles when I wore them.   I could have chosen “dud” outfits from past years like I did in my last outfit journal installment, but I really want this post to be about how my style has changed since previous summers.

The major reasons for my style change have been doing Project 333, keeping my outfit journal, having virtual styling sessions with Bridgette Raes, and taking on my “Love It, Wear It” challenge (LIWI). These four things have helped me to better understand what I like to wear, as well as what hasn’t worked for me in the past.   This increased awareness has helped me transform my style to what it is today.

Here’s a look at what I was wearing back in the summers of 2013 and 2014:

2013-2014 Summer Outfits 1-4

A few of my summer skirt outfits from 2013 and 2014.  I wouldn’t wear these looks today…

2013-2014 Summer Outfits 5-8

More 2013-2014 summer outfits – better, but need some tweaking for me to like them now.

Some of the features that the above outfits had in common were:

  • Knit blazers
  • A-line midi skirts (my skirts always look longer in photos, but they were still too long)
  • Formal-looking shoes (and flat/low-heeled in many instances)

These features are a lot of what led to the “churchy vibe” that I lamented when I started working with Bridgette Raes a year ago.  I often felt too dressed up in what I was wearing, especially in relation to the ultra-casual vibe of the area where I live.   I didn’t really understand what I was doing wrong, as I often liked my outfits, but I frequently felt out of place compared to those around me.   I wanted to tone things down so I would feel less formal and fit in better with my peers.

I still own about half of the pieces shown above and still wear most of them.   However, I style them in different ways so that I feel less dressy.   I’m more likely to pair cardigans or moto-style jackets with skirts and dresses these days, rather than knit blazers.   And I’ve found that changing out the shoes for more casual sandals has made a big difference in terms of looking less formal.

What I’d Change About My 2013/2014 Summer Outfits

Just for fun, here are some notes about what I would change about each of the above outfits if I were going to wear them today.  In some cases, only small tweaks are necessary, whereas in other instances almost a complete change is needed for me to want to wear the look now.

  • Striped blazer outfit: I really want to find a shorter and narrower black skirt, but I haven’t been able to locate one that works for me just yet.  I would switch out the skirt and wear more casual shoes, such as one of the pairs shown below.
  • Purple tank outfit: I love the color of the tank, but was no longer a fan of the ruffled front (so the tank is gone).   The skirt has been shortened since the photo was taken and I like it much better now.  I would wear a plain purple tank with the shorter skirt and one of my other pairs of black sandals (the pair shown was returned after just a few wears because the straps kept falling off my heels).
  • Black/grey blazer outfit: The skirt is the problem in this outfit and I no longer own it.  I would like the look with a shorter printed skirt (perhaps the zigzag skirt shown below).  For a more casual look, I would switch out the knit blazer (which I have passed on) for my black tie-waist cardigan.
  • Turquoise blazer outfit: I would wear a shorter and narrower skirt with more modern sandals.  I no longer own the tank and blazer, but I have another striped tank that I could wear with my cobalt cardigan.  That would be a more casual look that would work better for my life.
  • Coral blazer outfit: I still own all of the pieces shown, but may pass the blazer on soon (I’m just not as into knit blazers anymore).   I would prefer the look with my fuchsia tie-waist cardigan (shown here) and black shoes (the silver shoes are too light and don’t really work with the rest of the outfit).  I still love the skirt and it is actually shorter than it looks in the photo. I can also fold the waistband over to shorten it even more.
  • Black cardigan outfit: I would switch out the skirt and the shoes here. The skirt is too formal (and I no longer own it) and the shoes are too heavy.   I no longer own the top, either, as it was too ruffled, but I like the print and would wear something similar.  I really need to find some shorter and narrower skirts if I want to wear these types of looks and stay true to my current style aesthetic.
  • Green tank outfit: I still like this look with the exception of the skirt (which is gone).  If the skirt were shorter and narrower, I would wear the outfit today.   I love the color of the tank, but sadly the tank got too worn out and left my closet in July.   I would love to find another top in that color or slightly darker (emerald), as it’s one of my favorites.
  • Leopard print dress outfit: I still love and wear the dress, but I think the knit blazer is too long and formal for it.   If I need a topper, I would wear a tie-waist cardigan or denim jacket instead. I would also switch out the shoes, as I no longer like the style of the shoes shown.  One reader commented in response to a previous post that they look dated, but they were purchased in 2013.   Even so, they are no longer a favorite even though they are comfortable. It’s hard for me to find shoes for my fussy feet that don’t look “old lady,” but it’s a worthwhile pursuit!

So basically the main changes I would make would be the following:

  1. Wear shorter, narrower skirts
  2. Switch out the knit blazers for cardigans (unless I want to be more dressy/formal)
  3. Wear more modern, less heavy shoes
  4. Wear plain, non-ruffled tops

2015 Summer Outfits

Now let’s move on to my ensembles from this summer.  I have been wearing maxi-length skirts and dresses far more often than shorter versions, but I still have some mid-length options that I like.   Shown below are eight looks I have enjoyed wearing in recent months:

2015 Summer Ensembles 1-4

Some of my 2015 dress and skirt ensembles – I am much happier with these looks… 

2015 Summer Ensembles 5-8

Maxi dress and skirt looks are what I’ve been wearing most often this year.

As you can see, I now enjoy wearing asymmetrical skirts and dresses, as in the first three outfits pictured.  I like the way the asymmetry adds a bit of visual interest to the looks.   All of those skirts are shorter in real life than in the pictures, I think due to the camera angle when my husband does the photographs (we can’t seem to get it quite right…).

I’m not wearing toppers in most of my 2015 outfits because it’s been quite warm and I haven’t needed them.   When I do wear a topper, though, I usually grab one of my three tie-waist cardigans (see the black one above).  Those look best with the maxis and don’t overpower my frame the way longer jackets and cardigans can.  I sometimes wear my striped blazer (see the first photo above) with the blue dress, and I pair my denim and moto jackets with many of my summer ensembles. I’m really moving away from the knit blazers and have passed many of them on already. I do still like them with some skirt outfits but not so much with dresses (and definitely not with maxis).

In terms of shoes, I generally wear my plain flat sandals (either black or metallic) with my maxis and a few other pairs of black and metallic sandals with my shorter skirts and dresses. I really don’t need many pairs of shoes (the me of three years ago would cringe at that!), as I find that I wear the same few pairs over and over again. I will likely pare down my shoe collection soon, as I no longer like and wear many of my older pairs.  I am often hesitant to get rid of shoes (and pants), but it gets easier as time goes by and I find that I’m happy wearing just a few favorites and have little or no need for more.


I feel quite happy with my summer style these days.   It’s easy for me to get dressed and I have been rating almost all of outfits as “8”s or higher (with many “9”s and a few “10”s in the mix).  Over the past few months, I have been happy with almost everything I’ve been wearing. My track record continues to improve and I know it’s as a result of LIWI and my outfit journal.  Focusing on wearing what I love and taking notice of what doesn’t work has led me to make changes and hone my style. It has taken time, but it’s working.

I would still like to find a couple of shorter, narrower skirts to replace some of the older ones I’d like to pass on, but I haven’t been having much luck in the stores. It seems like almost all of the skirts on offer are maxis, minis, or pencil styles that look pretty corporate. I am looking for skirts that come to the middle of my kneecap and are straight rather than tapered in, which seems to be a tall order these days.   I may visit a few consignment stores to see if I can find some better options. I have been hesitant to do any resale shopping due to my poor track record, but now that I have a better handle on my style and am more deliberate about what I want to buy, I think I will experience more success these days.   We shall see and I will keep you posted…

If you are in the process of honing your style or if you’d like to make some changes, I encourage you to take some time to review your current season’s outfits, both those from this year and from previous years.   Look at what you love and what didn’t like so much – and why. If you’ve been photographing your outfits, the process will be easier, but you can still do a version of the exercise I did even without photos.   Just spend some time in your closet and jot down a few notes about your favorite and less favorite looks and why you did or didn’t love them.   That will be a good start to help you improve your style.  Repeat the process each season and I believe you will happier and happier with what you’re wearing.

Your Thoughts?

I would love to hear from some of you about what you’re learning about your summer (or for those in the southern hemisphere, winter) style this season:

  • What have you loved wearing and why?
  • Which looks have fallen flat? Why they haven’t worked for you?
  • What improvements could you make to your summer outfits?
  • What strategic additions do you need to make to your wardrobe to increase your outfit happiness quotient?
  • Could you possibly make the changes you want to make through shopping your closet instead of the stores?

I invite you to answer the questions above and share any other feedback you have on your current season style.   If you have comments on what I wrote as well, you’re welcome to chime in there, too. I will be back soon with my July accountability update and some reflections on my recent birthday and the upcoming last year of my 40’s.  Stay tuned…

43 thoughts on “Style Reflections – Summer Outfits Then and Now

  1. As I look from 2013 up to today, I see its not so much that your core style aesthetic has changed, but that you have updated your clothing to reflect more current silhouettes. For example, you tend to choose a close to the body fit above the waist with a flared skirt, to which you sometimes add a topper. In your churchy days, the skirt would always be a midi length, whereas today it could be an elliptical hem or a longer skirt, which actually balances your height much better, IMO. Instead of a fitted knit blazer, you now choose a sweater that ties at the waist and gives the same fitted feel through a more current, less stiff style.

    When you compare the fit of your clothing in the churchy days with the fit of your last outfit featuring the turquoise tank + cobalt skirt (which is beautiful, BTW), you will see what I mean about your style aesthetic remaining consistent.

    • Deby, I agree. The aesthetic has changed only slightly, and carries a similar style (a good sense of style) yet what’s most noticeable is that Debbie has released a number of outdated pieces from her wardrobe, or is combining the older pieces in a different manner, and is now wearing a current silhouette.

      Debbie, back in 2013 I had noticed that a number of your clothing pieces and shoes were dated. I never mentioned it because it was more important that you begin to shop less. I didn’t want to say anything that might induce a shopping spree. Plus there was nothing wrong with your clothes, you looked nice, but they just weren’t you, and didn’t fit your personality and your lifestyle. Your day-to-day look was a lot like what I wore to work back in 2006-2010, when I worked in a conservative office. One of the binds I got myself into when I had a large wardrobe was that I had so much I only wore each piece about once a month and nothing ever wore out. Ultimately it was hard to let go of perfectly good items, even though I could see they were becoming dated. Also since I shopped too much often I would buy too much of a similar style and after a few years when it became dated (I’m thinking ruffles. Ruffles on jackets, shirts) I found myself with lots of outdated, perfectly good pieces. I had to hold my breath and release them from my life, and promise myself next time I shopped I would buy less. I believe it’s better to own less so that we can invest in better quality, and when we have less it’s easier to keep our look updated. I’m not talking trendy, but to wear a current silhouette. Debbie, I love your new current silhouettes. You look relaxed, happy and friendly, and at home in your body, and a person whose style I would admire. And if I didn’t already know you, I would want to get to know you.

      • Oh Debbie, I so wanted to say the same thing as Terra did– about the style of your clothing looking dated in 2013, but I didn’t want to interfere with your style aesthetic or hurt your feelings! At that time, I didn’t understand the casual nature of your lifestyle. To me, your churchy look was synonymous with the kinds of outfits I wore for business in the early 2000’s, up toabout 2008, when I realized they were too fussy for my career. People I knew at work or met in business were always commenting nicely about how I was “rather dressed up” or asking “are you going someplace fancy after this?”. Over the past two years I have learned to understand the newer casual silhouettes and how they work with my body type, and for business attire. As a result, I feel like I fit into groups more instead of looking too formal. And now you have carried through your style aesthetic to today’s silhouettes!

      • Deby, I agree and much of what you have said applies to me too and why I was dressing that way and why I made changes. And Debbie, I also did not want to hurt your feelings or interfere with your process of discovering your true north in style.

        And I meant add at the bottom of my comment and got sidetracked is a rave about your photo. I love your photography. This ocean scene is outstanding. Lovely work.

      • That’s true, frugalscholar… I am having to let things go because they’re worn out for the first time in a long time (with the exception of workout clothes and sleepwear). I feel sad to have to let some old favorites go, but it feels good to know that they were loved and worn regularly.

    • Thanks for your observations, Deby and Terra. I think you are right that it’s more my silhouettes that have changed than my overall style aesthetic, but it feels quite different for me now. I feel a lot better in what I’m wearing and I’m happier with it. And yes, my current outfits are a much better fit for my lifestyle. I think I took what I saw on “What Not to Wear” a bit too literally and that’s part of how I ended up with the churchy vibe. Plus, I shopped resale a lot, which can lead to a dated feel if one isn’t deliberate in what they are buying. It probably would have hurt my feelings if you told me I looked dated and it likely would have had me shopping more, which wouldn’t have helped at that time. I DID buy too much in the past and felt guilty when I only wore things a couple of times per year. I had too much of the same styles but didn’t want to let things go because they hadn’t earned their keep. I’m glad I stopped the incessant resale shopping and took the time to decide what I really want and pare things down. I believe I will never have a huge wardrobe again, as I feel I dress a lot better with less and feel less overwhelmed. It’s a good feeling now… Thanks for sharing that both of you went through similar journeys. I’m glad we have all come out the other side!

      • Debbie, thank you for understanding why I never said anything about your outfits seeming dated. I came so close, so many times to suggesting it, but then backed off.

        You have highlighted one reason why I seldom shop in resale stores (although I take my own clothes there twice yearly). An avid reader of fashion magazines, I try to incorporate bits of current trends into my wardrobe each season along with my basic style aesthetic. Trends have varying lives, and sometimes longterm trends don’t work out for a variety of reasons. I cut my losses by taking “wrong” items to resale so that someone else can benefit from my mistakes while the items are still relevant and desirable.

        I also update my basic silhouettes about every two years. For example, the last few summers, I wore palazzo pants and tiered maxi skirts, but this year that looked boring to me so I’ve switched out the palazzos for newer slouchyankle pants in drapy fabrics and plain, less boho maxi skirts.

        When I go into a resale shop, most of the things look dated to me. I am also very picky about choosing natural fabrics (or at least synthetics that are not obviously so). I dislike bright clashing graphic prints and embellishments on tops–the hallmarks of fast fashion, which is a lot of what you see in resale shops even if the clothing is more current. From time to time, I will see a garment in a resale shop that is timeless, or one that I remember from years before that is still relevant. and I will purchase that, but only if it fits perfectly off the rack.

      • Me too. And oh dear Debbie, I never want to hurt your feelings, and I fear that I’ve hurt you now, and I would never want to do that because I adore you. I held back from making comments because there wasn’t anything wrong with your wardrobe. Yet since you are young and beautiful, tall and thin, I was rooting for you to begin to dressing in a younger, updated style, and now you are! When I look at photos of myself back when I was in my 40s I can see how matronly I looked, but at the time I didn’t see it. My husband and adult daughter told me that I was buying (new) clothes and combining them in a manner that dated me, but I didn’t get it at the time. When I turned 50 I began working in a progressive office and was able to ditch the type of skirt/jacket/shoe combos I wore previously. I began to be open to wearing new styles, and I embraced the fact that office-wear had evolved to a style aesthetic that was far more youthful than in past decades. In turn I began to evolve, and I felt younger and looked better in my 50s. Debbie, I see you following a similar path. At 49 you have found yourself, and you look fabulous. You are beautiful and you look youthful in an age appropriate way. And… you look far younger now than you did a few years ago. Enjoy being 49 and walk forward toward your 50s with confidence. Heck, 60 is pretty good too!

      • Oh, Terra–I can so relate to what you just wrote! I dressed abominably when I was in my mid 40’s. I thought I was fat, so photos show me dressing like I’m a widow from a very conservative environment. I used to wear ankle length black dresses with undefined waists, black opaque hose, and chunky black shoes–it was my uniform. If it wasn’t so pathetic, it would be laughable! Who knows what I was thinking–I must have had some body dysmorphia going on because I thought I looked sophisticated in these drab duds. Now when I look at photos from that time I see how I looked so totally “off” was my style compared to my coworkers.

        When I was 49, I started dating a very charismatic man who persuaded me finally that there was nothing wrong with my figure that I needed to hide beneath swathes of black fabric. Our relationship did not stand the test of time (in fact, I found out a few weeks ago that he had passed away suddenly), but the confidence he instilled in me has stayed with me. Today at 61, I weigh 10 lbs less than I did at 49, and I wear fitted stylish clothing now–and I’m not afraid of colors! I am not exactly svelte–I just learned I am the same height and weight as Amy Schumer–but like Amy (who is my hero because she is outspoken and is not afraid to be human), I think I look pretty good for my age, or any!

        And Debbie, you look much more relaxed and approachable in your new looks than you did as a church lady!

      • Maybe there is something about the mid-40’s and not dressing well, but I think I dressed WORSE in my mid to late 30’s actually. I could have been on “What Not to Wear” back then, but after I started watching the show, I took Stacy and Clinton’s advice a bit too literally and ended up as the “church lady.” I’m glad to be finding a happy medium these days. I have definitely struggled with body dysmorphia over the years and it’s still an issue for me. I always think I look bigger than I actually do, which is a remnant of my many years of having eating disorders. I love that you are so confident about your body these days even if you are a bit heavier than you were when you began that relationship in your late 40’s. I am a BIG fan of Amy Schumer and I think she is fabulous and looks beautiful! It’s so refreshing to see curvier women on TV and in movies who are still playing sexy and attractive characters. I’m sure you look great for your age or any age, Deby. I always wish I could see all of you. I know what some of you look like, but most of you are just names to me. I wish we could have a big party where we could all meet!

      • Deby and Terra, neither one of you hurt my feelings, but you might have if you told me my clothes were dated two years ago. It’s easier for me to accept that looking back than if I were still wearing such outfits now. Deby, I think your plan for keeping your wardrobe updated is a good one. If you would be interested in writing a guest post about this, that would be great! I was just thinking about that topic last night – how to stay current without overshopping. I was pondering how many new pieces per year a person might need to add for that purpose. I’m not sure, as I still add too much, but I am continuing to refine my style and create a workable wardrobe.

        It makes sense that resale shops often have a lot of dated items. Sometimes it is really obvious, but other times not so much. I think it’s a good idea to stick to classic pieces when buying secondhand, unless one finds current trends there that they want to play with for a low cost. I have noticed lower quality overall at resale stores lately and figured it was because of “fast fashion.” I also think my taste and standards have changed, so I don’t see as much that I like in such stores now. I don’t see as much that I like anywhere anymore, which is a good thing, as it pays to be selective and know one’s style aesthetic and lifestyle.

        Thanks for all of the wonderful encouragement and compliments, Terra. You are always so kind and I appreciate that. I also appreciate the look ahead to the 50’s and 60’s. I am nervous to turn 50, but it’s not just about my looks. It’s also about where I am in life, but that will be a topic in my upcoming birthday reflections post (one week later but still relevant).

      • I would rather write a guest post about updating your wardrobe than about caring for winter knits!

      • I would be delighted for you to write this post, Deby, and I’m sure it will be beneficial to readers. Whenever you want to do it, I welcome it!

  2. What I see that is the common thread of the previous looks is the half half proportionate or 1:1 ratio that you’ve got going on it all of those outfits. These all shorten your height despite your tallness and give a matronly vibe. I agree that a shorter skirt paired with a longer top will give you a more flattering proportion of 2:1 or close to that. Also it looks more youthful and modern.

    I see that your dresses and longer skirt outfits all give you an uneven proportion of 2:1. Either that or you are wearing single pieces (dresses) or columns of color (same color in different shades throughout from the top to the bottom piece). I believe that is why you like the maxi skirts better than those flare skirts (which exaggerate your hips also imo). Your dresses also all taper at the smallest part of your waist. I also see greater use of verticals (vertical stripes, vertical leopard pattern, maxi skirts). So you look significantly taller in these new photos despite being the same height as before. This gives a more modern appearance that also highlights your shape. I would use shorter jackets or shrugs with those older outfits.

    • Exactly the 2:1 ratio makes a huge difference. Debbie, in your latest non-churchy outfits, compare #2 and #3 (the one with the asymmetrical red striped skirt and black top).

      #2 (the sleeveless striped stop with the black skirt) looks great on you. #3 looks good too, but would look more balanced in the 2:1 proportion if you belted it at the waist to guide the eye, or tucked the top in.

      like you, i only wear maxi dresses now.

    • Very good points, Margaret and Nutrivore. I agree that the proportions in the recent outfits are better. I’m also about 10-12 pounds thinner than I was a year ago, so that has some bearing on looking taller and slimmer, too. But I know that the clothes have a lot to do with it. I would hate to look matronly and am glad that word applied to the older looks, not the recent ones… That’s the last word (or one of them) that I want to apply to 49 year-old me!

      I will definitely try shorter jackets or shrugs with the mid-length skirts and dresses, as I know it would be a better look for me. Regarding the grey and black striped outfit, that is a dress instead of a skirt and top, which makes things much easier… The black top with the red and black striped skirt has ruffles on it, which makes it trickier to style. It could work with a belt, possibly, but I’m not sure. I am a bit “belt-challenged” and only have two, but I will give it a try. I have tried tucking in the past and never liked how it looked and most of my skirts have elastic waistbands (and are too loose for me with my weight loss). I won’t give up on tucking, though. I can see how it might work with the right garments. Dresses are much easier than tops and skirts because it’s one and done 🙂

  3. Damn Debbie, you look hot! You go girl. Happy 49th!
    I’m in the last year of my 30s and just want to start putting my life back together now that we’re finally back in the QC. I’ve managed to buy a couple of things here and there to help me scrape by, but definitely have some work to do to get the closet in order.

    • Thank you so much for the nice compliment and wishes, Claire. Best of luck to you in the last year of your 30’s. It sounds like you are doing much better following your move. I hope your closet will be more in order very soon.

  4. The style you wear now flatters you so well. As I think I may have similar body shape to you,I want to take pointers from you about how you put outfits together.

    • Thank you, Fiona. If you have any specific questions for me, please let me know. I would be happy to try to help. I’m still figuring things out for myself, but if I can offer you any guidance, it would be my pleasure to do so.

  5. Congratulations on what looks to me like a huge improvement! Two things you didn’t mention, which I noticed straight away… the second set are bolder, simpler outfits, with less fussy detail. This makes them look more modern and confident (I think ‘churchy’ is as much about looking fussy or demure, rather than any particular length of skirt etc). The second change is that the first set all follow a bright top-neutral bottom formula. The recent ones are more adventurous and mix things up – a red skirt, a bold vertical panel in the black/white maxi dress, and my favourite – the turquoise tank + cobalt skirt. Do try lots more adventurous colour blocking!

    Also, I like the length of the slightly longer black skirt. Although I know others are saying ‘shorter = less dowdy’ i’m not so sure, it could just be the style, or the way they are combined in outfits. The ‘midi’ length seems to show-case your pretty ankles and shoes. Have you tried cropped pants?

    • Very good points, Alice. I have noticed that I really don’t like fussy details anymore. I have even gotten rid of some jewelry pieces that I used to love but started to feel too big and ornate to me recently. It was a spur of the moment choice to pair the turquoise tank with the cobalt skirt, but I really liked it. I will definitely try more adventurous color pairings in the future. I would love to get another bright skirt, as that cobalt one is really the only one I have (except for the red and black striped one, but I am more limited there). I still like that longer black skirt, too, and so does my husband. It is one of my most long-standing wardrobe pieces and I still like it for casual with a tank top and maybe a shrug of tie-waist cardigan. I haven’t worn cropped pants in a long time. I went through a period when I wore those instead of skirts and dresses, but not recently. Maybe I should try some on again…

  6. Sorry, just noticed you asked a whole bunch of questions to which I didn’t reply. I’ve had over a year of my project to sort out my wardrobe. There have been some improvements, especially in identifying things that don’t work (shapeless tops and jackets, very straight trousers with matching shoes,, a too corporate/masculine ‘vibe’) but there is still a long way to go!

    • Thanks for sharing your progress, Alice. I think it’s good for us to acknowledge how far we’ve come even if we still feel we have quite a ways to go. Identifying the things that don’t work is an important part of the process. Best wishes for continued growth and progress!

  7. I agree with the proportions and what a difference it’s made. My favorite is the the royal blue dress with no waistline, longer length, and snazzy, updated sandals! Second favorite is the black/white ensemble next to it… The higher defined waist looks more in proportion on you, along with the longer length on the skirt. Lookin’ good!

    • Thanks so much, Karen. Both of those outfits are favorites of mine, too. The striped ensemble is actually a dress rather than a top and skirt, which makes it very easy to wear. No tucking or belting required… Maybe I should look out for more dresses along those lines.

    • I appreciate your kind words, Mette. I agree that I should show off the small waist while I have it. It may not last forever as I inch toward my 50’s, but I’m happy to have it now 🙂

  8. It really is amazing what a difference shoes can make. I’m so happy there are more fashionable comfortable shoe options now, even more than a few years ago. I really love your looks in all the current outfits and like you I never would have imagined myself in maxis a few years ago, but now I love them. I would reconsider pencil skirts, I have found that its the material that makes a huge difference, ie ponte knit or twill totally change the vibe away from corporate. I’ve also changed some of my corporate skirts feel with ultra casual items, tanks, tees, denim and casual shoes, that has helped more often that not. I wouldn’t buy anymore of those now, but can still wear some of my old ones. Thanks for the updates and I like keeping up with your evolving style and rationale for changes. I am definitely tweaking my looks to fit my lifestyle for today, not yesterday or tomorrow!

    • Yes, shoes can make a huge difference, Natalie, more so than I ever used to realize. Good point about the pencil skirts. I agree that the fabrication and pairings can make them look less corporate. Good for you for making your corporate skirts work for casual wear and for tweaking your looks to fit your current lifestyle. Way to “make it work,” as Tim Gunn would say 🙂

  9. First off, I love your summer 2015 look! I think you looked pretty before and you look pretty now, but the main difference is that you look more comfortable in your skin now. Those earlier outfits were kind of fussy, and they just didn’t suit your personality or lifestyle as well, based on what you’ve said.
    For myself, I’ve been doing a modified LIWI this summer – modified because sometimes I will force myself to wear an item just to see how I look and feel in it. If it doesn’t get a high rating, I may try it in another combo or it may go onto my probation pile (if it’s not recalled by the end of the season, out it goes).
    What I’ve discovered is that I like color and subtle prints more than I thought I did. I feel most comfortable in pants, but I like to wear dresses for dressy occasions. I’m happy with a modest number of neutral colored pants, and I introduce color with tops and toppers – but I do have a few pairs of colored or patterned pants and one print skirt for warm weather to be worn with neutral tops. I’ve also realized that while I love the neutral blazers I have for work, outside of the office I prefer more casual jackets, cardigans or V-neck pullovers. I did buy a few summer tops, but I’ve also revived a few from my closet that I was “saving” for going out – with jeans or cropped chinos they look cute and casual.

    • Thank you for your compliments on my current looks, Murphy. Yes, they suit my personality and lifestyle a lot better than what I was wearing before and I’m much happier in them. Good for you for modifying LIWI to suit your needs. I like the idea of having a probation pile and having a rule to let things go at the end of the season if they are not recalled. Sometimes it IS about how we pair things that determines whether or not we’re happy with them, so it can be worth giving something a second chance. You seem to be learning some valuable things about your style. LIWI really does help us to figure things out. Best wishes for future style lessons!

  10. I like your new summer style, Debbie. It’s very modern, current and flatters your body a lot better. I believe it’s more suitable for your casual lifestyle too?!
    I’m having a similar summer and doing a Wear What You Love challenge myself! I’m learning so much about my wardrobe and honing my style as well. I see a remarkable shift in my style compared to two summers back.

    I believe my style to be ‘Comfortably Dressy’ and I now wear more and more outfits in my work from home lifestyle that feel ‘right’ and represent my style aesthetics even in a casual environment. I’m so glad to hear you’re having a great summer too! Keep it up!

    • Thanks, Maneera. Yes, my current style is more suitable for my casual lifestyle. How great that you are doing a “wear what you love” challenge this summer. It really can help us to learn a lot about our wardrobes and style. Comfortably dressy is a good style descriptor… I’m glad you are happy with your outfits and feel that they represent your style aesthetic. It’s a good feeling, isn’t it? I wish the best with your ongoing style learning and evolution!

  11. Congratulations Debby. These pictures show just how far you have come in style. You look so much more confident and contemporary in the new style. 3/4 sleeves, longer blazers with skirts and dresses and full skirts now look dated. You new style with softer cardigans, and simple fitted dresses is perfect. I am also having problems finding good skirts, so am focusing on dresses, which often look better than a mismatched skirt and top anyway. I rarely wear formal jackets now, but find cropped denim jackets (various colors) really useful with dresses. I know you don’t get cold weather like we do in UK, but I’m looking forward to seeing your style for cooler weather. I find jersey dresses with dress length cardigans and slim skirts with long sleeved bretton T shirts (over, not tucked in), opaque tights, and boots work well.

    • Thanks for your comment, Lynn, and for your suggestions. I like the idea of cropped denim jackets and will keep my eyes open for that style. You’re right that we don’t get actual COLD weather where I live, but it does get cool and I tend to feel the cold more than most people. Your ideas for cold weather ensembles sound good to me. You know I love my stripes 🙂

  12. Your old look is very reflective of the WNTW formula!! I liked that show well enough but looking back they were SO limited in the way that they encouraged people to dress that everything looks heavily dated already. I think part of the reason you look so much slimmer this summer is that you’ve created an hourglass rather than rectangle shape with your clothes.

    I feel like my wardrobe hasn’t changed too much this summer – I tried a maxi dress (hated for summer! so much fabric!!) and traded t-strap sandals for ankle-wrap ones (love!). I’m also excited to see that flared legs are coming back for fall. I do like skinny jeans but it’s gotten pretty boring having no other options to choose from in stores.

    • Good point about WNTW, Sara. I wonder how many other women out there followed their advice to the letter of the law and ended up looking “churchy”… Probably quite a few! In regards to my looking slimmer, the outfits are only part of it. I have actually lost 10-12 pounds since last summer, so that’s a big part of it. But I do like my current outfits SO much more and I like to show off that I have an hourglass frame. That may not always be the case, so why not flaunt it now? I’m excited for flared legs to come back, too, even though I was a late adopter of skinnier styles. Why not embrace both? I also like ankle-wrap sandals, but have trouble finding ones that work for me with my protruding ankle bones. I did find one pair that works pretty well because the ankle strap is a bit lower (the black ones I’m wearing with my red and black striped skirt). Those are a new favorite of mine. Best wishes with your fall wardrobe!

  13. Very nice outfits. The 2015 looks remind me of a post that you did some time ago. You had included some photos of people with outfits the you admired and wanted to have that look. I’d say that you’ve been successful. Still love the red skirt and it looks even better with those shoes and that top.

  14. Thanks, Tonya! Do you mean this post?: That was almost exactly a year ago and… you’re right! I do seem to have achieved my goal and that makes me very happy. Yes, the red skirt is still a favorite and I love my new black sandals that I’ve paired with it above. I wear those all the time. Hope your summer wardrobe is treating you well. You seem to have things pretty well dialed in these days, which is great!

    • Yes, that’s the one that I was thinking of. Your new outfits have the same vibe as those pictures. My summer wardrobe is good. I’ve been enjoying simpler outfits as well.

      • That’s wonderful feedback! It’s good to know that I’m on the right track. I’m glad you are enjoying your summer wardrobe, too. I’m sure I would like your simpler outfits, especially since you are also a fan of black, grey, and white 🙂

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