My Wardrobe, Myself

The intersection of clothing, emotions, and life

This is the third and final installment in my three-part series about what I no longer wear. In my first post, I explored two types of garments that I previously loved wearing but no longer do: skirts and blazers. I reflected upon how the combination of certain types of skirt and blazers created an overly-formal vibe that didn’t work with my casual lifestyle. In part two, I showed how I progressed to the interim outfit formula of maxi-length skirts and dresses paired with cropped or tie cardigans. I also shared the current state of my skirt wardrobe and mused about whether or not skirts will continue to be part of my summer style.

Today, I look at how my style preferences have evolved and what I’m wearing now instead of skirts and blazers. I also highlight some of the reasons for my style shifts and what these changes reveal about my current style preferences and my future sartorial journey.

New Preferences: Cropped Pants and Mid-Length Dresses

After I went through menopause in 2016 and my body changed (more on that below), I started to migrate more toward wearing cropped pants in warmer temperatures rather than skirts. This shift in terms of my bottom pieces has continued as the years have gone by. My current collection of cropped pants is pictured below (I also have a few other pairs that I wear only at home):

my cropped pants collection

This is my current collection of cropped pants that I wear a lot in warm weather. 

I began to feel more attractive and comfortable in pants rather than skirts, so I gradually let go of most of the skirts that I owned. As I mentioned in my last post, I currently own only four skirts – and I wore just one of them last year. Although I moved away from skirts, I continued to like wearing dresses. However, my preferences have shifted to styles other than my previous mainstay of maxi lengths.

I now generally favor midi length dresses, as well as asymmetrical and high-low silhouettes (shorter in the front and longer in the back). I currently own eleven dresses, only two of which are maxi-length. Here’s a look at the dresses that are currently in my closet:

my current collection of dresses

These are the eleven dresses that I currently own, mostly midi-lengh. 

Included below is a collection of photos of me wearing my cropped pants and dresses. I don’t have many outfit photos from 2018 to the present, as I mostly stopped taking them, but this gives you an idea of my current warm weather style. Even though some of the photos are from three or four years ago, I still like and would wear these outfits now:

recent cropped pants outfits

Here are some recent cropped pants outfits that I’ve worn – and would still wear today.

recent dress outfits

These are some dress ensembles that I would still enjoy wearing today. 

A few notes about the above photos… Unfortunately, the black jacket paired with the turquoise dress belonged to my friend, but I would wear such a jacket now if I could find one that fit me properly (hers was a bit too small for me and wouldn’t close all the way – I just put it on for the picture). Also, I’ve had the hems taken down on some of the cropped pants to a more appropriate ankle length, or at least as close as I could get with my long legs. I no longer own the first pair of pants shown, but I wear the top with other pairs of black cropped pants now.

Why Dresses Instead of Skirts?

Although I used to love wearing outfits that paired short, fitted tops with flowing, streamlined skirts, I now much prefer to wear looser-fitting, body-skimming dresses, like the ones pictured in the last section. These dresses don’t accentuate my midsection or require that my stomach be ultra-flat or sucked in. I can breathe more freely in the dresses that I favor, and I also feel more elegant in them.

As I mentioned in my last post and other previous essays, “elegant” is one of my three style guideposts (introduced in this essay), along with “dramatic” and “polished.” Dresses often tick all three of those boxes, plus I appreciate the “one and done” quality of dresses. They’re easy to style, although toppers for dresses can sometimes be tricky due to proportion issues. The tie cardigans I showed with my dresses and skirts last week work well for me, but I’d like to find one or two alternate options to incorporate more variety. I’m open to any suggestions you might have…

New Preferences in Blazers

I’ve discussed my move away from skirts toward dresses, but as my style evolved, I also stopped liking to wear blazers. As I worked to shed the “church lady” aesthetic that I decided was too “proper” and dressy for my lifestyle and personality, I ended up purging all of the pieces in my blazer collection. Before doing so, however, I tried pairing the blazers with pants and jeans, but they looked too short in that combination. I felt like I was wearing a shrunken hand-me-down, rather than a jacket that was tailored for my tall frame, so I opted to pass all of the blazers on.

The “blazers” in my closet today can be more accurately referred to as long jackets. They’re much longer and less tailored than my blazers from 2006-2014 that were pictured in part one of this series. I only own three such jackets, and they’re reserved for wearing solely with pants and jeans, similar to how they’re pictured in the stock images below:

current long jacket collection

My current version of a “blazer” – longer and less tailored. 

In contrast to my old-school blazers, my newer jackets have a casual vibe to them that’s more in line with my 2021 lifestyle and style aesthetic. I can pair them with a knit top, pants/jeans, and short boots or sandals to create an outfit that’s suitable for most of the occasions in my life. I feel attractive in these pieces and just dressy enough to be in line with my style guideposts, but not so dressy that I feel out of place in terms of where I live and how I spend my time.

Moving on From Old Favorites

To sum up some of my key points from this series up to now, I no longer pair skirts with short blazers, and I’ve done away with the latter altogether. The four skirts I still own have been increasingly gathering dust in my closet in recent years, as I rarely reach for them anymore. Skirts and blazers were part of my signature style for many years, but then I experienced a style shift that led me to move away from them and toward dresses and cropped pants outfits instead.

Sometimes we need to let go of clothes that were previously among our favorites and played a key role in our style identity. The Debbie of the late aughts and early 2010’s was known for wearing skirts and dresses on virtually all warm days and evenings. But that was a very different Debbie than the one who is writing this today.

The 2021 Debbie has endured menopause, a seemingly interminable gray hair transition process (which I’ll be sharing more insights about soon), the deaths of a few dear family members, and a long period of chronic pain and illness. She’s also struggled with her identity, her sense of self-worth, and her place in the world. The “church lady” is gone and so are all of the remnants of her wardrobe.

Perhaps moving on from long-loved elements of our style is a critical part of our overall metamorphosis in life. Maybe I brought the A-line skirts and short blazers into my metaphorical chrysalis, and they didn’t need to accompany me when I emerged as a better, brighter version of myself. In some ways, it feels like just yesterday that I started Recovering Shopaholic as a way to help myself and others shop less and pare down our overstuffed closets. Yet in other ways, it feels like a virtual lifetime ago. I’m still me, but I have evolved – and I’m continuing to evolve.

My Style Today

On my next birthday in August, I’ll be 55 years old. I’m in a much different place in my life – and in my mind – from the me of the throwback photos in part one of this series. I’m not only older now, but I’m also wiser, in many ways due to the introspection I’ve done through blogging for ten-plus years (I had three other blogs before Recovering Shopaholic). I’m now trying to determine what my next chapter – perhaps my final chapter – will be.

My vision for the future still looks cloudy. I’m not sure who my future self will be – and what she’ll look like. I don’t see her dressing like my forty-something self, though, complete with flared skirts and blazers. I see her wearing what she wants to wear, not what two television personalities told her she should wear. I see her marching to the beat of her own style drum, rather than cow-towing to the whims of the “fashion gods.” I envision her as being far more comfortable in her own skin and a lot more aware of her wants, desires, and preferences. I visualize her as being free to be her true self and free to express her creativity in her life pursuits – and in her clothing.

I see my 2021 – and beyond – self dressing more and more like the “Looks I Love” images from my July 2020 personal style post, some of which are shown below:

style inspiration outfits - black and white

Black and white style inspiration outfits.

style inspiration outfits - black with denim

Black with denim style inspiration outfits. 

I’ve been steadily moving toward the above direction in how I dress ever since I defined my “style guideposts” last summer. Taking that action brought increased clarity to how I want to look on a day-to-day basis. I always strive to have my outfits – for all areas of my life – meet the “dramatic, polished, and elegant” description that I created to reflect my ideal style. Sometimes my ensembles don’t meet all three style descriptors, but they’re usually in line with at least two of them.

As I mentioned above, I don’t take photos of my outfits very often anymore. I mostly stopped taking them in 2018 because I was too critical of my appearance while going through my gray hair transition and dealing with menopausal body changes and weight gain. As a result, I don’t have many recent examples of my style to share with you. However, the following photos reflect how I like to dress today, even though some of them were taken several years ago. I no longer own all of the items shown, but I have very similar pieces in my current wardrobe that reflect my ideal style aesthetic. The photos of my summer style shown earlier in this post are also very much in line with how I like to dress now.

how I like to dress now - part 1

How I like to dress now – some cool weather ensembles. 

how I like to dress now - example 2

Examples of how I like to dress now – mostly cool weather outfits. 

Black remains the most prevalent color in my wardrobe, and I often pair it with one or two other cool-toned hues, as well as a warm tone here and there. I’ve embraced red a lot more since early 2020, and it’s now one of my favorite colors. Stripes remain a mainstay, but I also enjoy wearing other prints that are grounded in black.

Although I’ve pared down my jewelry collection considerably over the past seven years, I could streamline it still more, as I typically reach for the same handful of bold, minimalist pieces over and over again. The same can be said of my shoes and handbags, and I’m now trying to find replacements for some of my tried-and-true favorites that are becoming worn out (I’ll be addressing shoes in an upcoming post). I hope that I’ll also be able to be more minimal with my clothing as time goes by. That’s something that I’ll continue to work on – and write about here!

Conclusion, Coming Attractions, and Your Thoughts?

I hope you enjoyed this three-part series about some of the things that I no longer wear – and why. I hope it helped you to reflect upon your own style evolution, as well as the direction you’d like your style to take in the coming months and years. While some of you may have already been clear about your wardrobe likes and dislikes, perhaps taking time to consider what you don’t want and what you no longer wear has brought increased clarity for those who needed it.

In future posts, I’ll share some of my current favorite pieces in various areas of my wardrobe and highlight why they work so well for me. I’ll also continue to write about my adventures in honing my style and paring down my wardrobe, among other topics.

I’d love to read about what you learned from these last three posts. Some of you already shared about your style evolution in the comments section of the last two posts, but I welcome additional insights now from anyone who wants to chime in. Here are a few more questions for you to answer if you’d like:

  • How has the past year of lockdowns, quarantine, and working from home affected your style, if at all?
  • How do you envision your wardrobe and style in a post-pandemic world (which I hope is coming soon)?
  • Are you feeling the desire to dress up more now – or less?
  • Has your color palette shifted recently? What about the silhouettes you like to wear?

As always, I look forward to reading your thoughts. Have a wonderful weekend, and I’ll be back soon with another post for you.
Buy Me a Coffee at

17 thoughts on “What I Don’t Wear Anymore – Part Three (What I Like to Wear NOW)

  1. Lori says:

    Debbie, I really enjoyed this three part series. I don’t know if you feel the same , but for me, letting go of the GUILT of “letting go” has been one of the best attitude changes I have had in the last year. I also read this article
    which was a new way to determine what my style recipe is. I continue the KonMari process, albeit, in a much less dramatic fashion. I will go into my closet and realize that I never wear something and actually don’t WANT to wear it as it doesn’t spark joy and put it aside in a giveaway pile. I think that this past year of isolation and reflection has made a difference in my priorities. I want to dress to make myself happy and don’t really care about what anyone else is wearing! I am sure that we will all continue to grow and change and that is a good thing!

    1. Debbie Roes says:

      I’m so glad you enjoyed this series, Lori! Yes, it does feel good to let go of guilt around letting go of the things that don’t work for us. I still battle that sometimes, but it’s getting easier to push the guilt away. Thank you for sharing the link! I look forward to checking out her process. Her blog overall looks interesting. I always like to find style bloggers over 50 to follow. I love what you wrote about your new priorities and wanting to dress to make yourself happy. I hope that’s what a lot of us have gotten – or will get out – of this challenging time we’ve all gone through!

  2. Terra says:

    Thanks! I enjoyed this glimpse Debbie. ❤️

    1. Debbie Roes says:

      You’re welcome, Terra. I’m glad you liked it!

  3. Rachel says:

    ok, this is interesting: over the past 5 years or so, I have also largely stopped wearing skirts; adopted loose, cropped (just above the ankle) pants as a wardrobe staple; swapped all of my formal blazers – and cardigans, actually – for unstructured jackets and jacket-sweaters; and traded most of my fitted-waist dresses for looser ones. Part of this is my personal preference…or what I ASSUMED was my personal preference – but I wonder if the fact that style and trends and fashion overall have generally moved in that direction as well on all those fronts as well (likely in part for many of the reasons you mentioned, but also just because it’s felt like a newer, fresher silhouette) could mean that you, and I, and thousands and thousands of other women, have subconsciously absorbed that reality… and that’s possibly part of the reason we don’t feel comfortable in the (now objectively dated and less-fashionable) skirts and fitted jackets and dresses that we used to wear?

    Either way doesn’t make it any more or less valid a choice! It’s just interesting to try to parse motivations, and our awareness of all the reasons for our decisions. I’m a bit younger than you are, and my body hasn’t changed much over that time, I just…started feeling like I was more comfortable in that silhouette – and it didn’t occur to me that this evolution wasn’t just unique to me until I read this and realized that most of the people I see on the street when I do my daily lockdown-escape walks now dress this way too. Fascinating.

    1. Debbie Roes says:

      Very interesting, Rachel! You may be on to something about our eyes adjusting to new trends and silhouettes. I always say that I’m a “slow adopter” and that I’m not overly interested in following trends, but I think that we can’t help but be affected by what others are wearing and what we’re seeing in the media and in stores. Often when new trends come out, I don’t like them much at all! In fact, I was NOT into ankle-length pants when they first arrived on the scene, probably because finding pants that are long enough was a lifelong problem for me. But now I love that look, so I think my eyes and brain just got used to it such that I ended up embracing it. I wonder if that will happen with high-waisted pants and jeans. Hmmm…. Thanks for sharing your observations. It definitely gives me some food for thought! But you’re right that our choices are valid regardless of whether they’re unique to us or not. As an aside, your comment about “jacket-sweaters” makes me want to look out for those. That just might be a good new type of topper for me to try!

  4. Katrina B says:

    First of all, YOUR HAIR!!! So beautiful! Wow! Also I absolutely love your current looks and your future style/”Looks I Love”. Really a perfect embodiment of dramatic, polished, and elegant. Your goal for future Debbie to wear what she wants to wear is a good goal for everyone. There are so many styles available now, and they change so fast, it’s hard to see how we could be “in style” or following someone’s rules all the time anyway. I often joke that I’m wearing the same thing I did in 1973, and even though it’s not literally true, there are many styles that I have continued wearing through the decades because I just couldn’t see myself in whatever awful fashions were current. However, I’m still a sucker for rules and guidelines, see my thoughts on color palette below.

    I don’t think I’m even going to try to analyze or describe my style right now. The last couple of times I’ve done so, I later realized I was describing my 2019 style. I have absolutely no idea whether I would be comfortable dressing the same way now. Weight gain is one thing, but the level of dress here has dropped below even our former, extremely casual state. I wonder if even my smart casual clothes will feel too formal for work now. I have a lunch date in 3 weeks so I will be able to test the wardrobe – starting with can I fit into anything – and see if my outfits seem “right.” Office appearances probably won’t be required for another couple of months, so I have time to think about it.

    My color palette is a problem. I didn’t completely agree with “Light Spring” when I was analysed many years ago, but I tried! After a while I realized I didn’t wear most of the colors in that palette because even the “light” versions of the colors were too bright for me. But that analysis was done when I had very bright golden blonde hair, and although the color analysis was not supposed to be swayed by hair color, it was hard to ignore. Now my hair is a combination of silver in the front and pale cool brown in the back, which makes spring colors look quite outlandish. So now I’m back where I started, which is wearing colors I like, rather than what has been prescribed for me. This was a problem in the past, since I like ALL the colors, and would buy any pretty thing. However I think now I’ve had my flirtation with the brights, the darks, the reds, the oranges, and I love my closet full of light blues and soft greens. Hopefully this will keep me from going off course.

    I look forward to your shoe post, as shoe preferences are something that is always changing for me.

    1. Debbie Roes says:

      As always, I appreciate your detailed and thoughtful reply, Katrina, and thank you for your kind words about my hair! I also appreciate your validation that my current looks and future style direction are in line with my style guideposts. I agree that wearing what we want is a good goal for everyone! It’s very hard to keep up with what’s most current anyway, and things change so much that it’s almost like anything goes anyway…

      I’m sure a lot of people are in a similar boat as you are in terms of not knowing how to describe their current style. Saying that what you describe is more like your 2019 style makes sense, as we’ve all been in basically a “holding pattern” since early 2020. It’s good that your lunch date will give you a chance to experiment a bit with how you’d like to dress now for being out in the world. As for colors, that can definitely be challenging. I sometimes wonder if my color palette should change now due to my lower contrast level with the lighter hair. I have shifted my colors a bit to less vibrant hues (and more red), but I haven’t made a dramatic shift. I’m glad you have a greater awareness of your love for light blues and soft greens after doing some experimentation. Sometimes we need to try a lot of things to get a better sense of what we like. It’s a bummer when color analysis isn’t accurate or doesn’t feel right for us. It’s hard to believe that hair color wouldn’t make a difference, as it’s such a big part of our overall coloring. I guess the good news in what you wrote is that you’re now wearing the colors you like most. Yay for that!

  5. NATALIE says:

    I have found this three-part topic interesting. I only wear dresses, which some of you may find unusual. I feel comfortable in skirts but not dresses. I am short-waisted and long-legged, so I find finding dresses that fit me correctly very frustrating! I’m desiring to dress more elegant casual. This is me normally, but the winter before the pandemic, I was dressing very casually and wearing tennis shoes. This was very out of character for me but was because I was in severe back pain. This is now under control. I’m hoping now to start back wearing my elegant casual clothing. Shortly before the pandemic, I Marie Kondo’ed my wardrobe. What a mistake! I literally spent several thousands replacing my wardrobe!! I will never do that again! You are right…there is a closet set-point!

    1. Debbie Roes says:

      I’m glad you enjoyed this series, Natalie. I struggle to find dresses, too, for the same reasons you mentioned, but I enjoy wearing the ones I do find that work. I like the description “elegant casual” and enjoy dressing that way, too. That’s great that your back pain is now under control and you can get back to dressing how you’d like. I’m sorry you have regrets about Kondo’ing your wardrobe. I’m sure you’re not alone in that respect! Because I sometimes change my mind about letting some things go, I usually put them aside somewhere else in my house (outside of my closet) for a month or two before I actually get rid of them. Yes, the closet set-point is a real issue for many of us, which is why downsizing gradually can be a better option. But we all make mistakes and learn as we go. It sounds like you’ve learned some good lessons from what you’ve gone through, which is what’s most important.

  6. Jenn says:

    I think the cropped pants, dresses, and less tailored blazers are great looks for you, Debbie, and your hair looks fantastic! I wonder if referring to yourself in the third person may be a brilliant way to observe your style more objectively. I might have to try that!

    I feel a bit “stuck” style-wise, likely due to the pandemic. But now that I’m five days post-second vaccine and beginning to make social plans, I expect to actually wear more of my clothing items soon.

    For the past year, I think I’ve allowed myself to be influenced by the emphasis on neutral colors. I like wearing neutrals on the bottom, but when I recently pulled the tops I LOVE from my closet and arranged them on a rack, I saw a lot of color. I’ll still enjoy wearing my oatmeal and gray sweaters, but I’ll make sure to add interest to them with accessories.

    And Katrina, years ago, a color analyst told me she’d never had a more challenging time classifying a client, and after about three hours, she dubbed me a Light Spring. Like you, I found many of those colors too bright (and “hot”) for me. I’ve since read that Light Springs and Light Summers are “sister seasons” and often misclassified for the other. After much experimentation (and many mistakes), I’ve found my best colors are primarily cool, light-medium in depth, and not too muted nor too bright. Lavender is my absolute favorite color to wear.

    1. Katrina B says:

      Nice to hear you had such a similar experience! I definitely feel less overwhelmed by cooler, softer colors. And how funny that your analysis took so long! Mine took so long that after 3 hours we had to stop and eat lunch before getting back to it. At this point I really think that soft/muted/neutral people are impossible to classify and so it just depends on the day or the analyst you see.

    2. Debbie Roes says:

      Thank you so much for the compliments on my outfits and my hair, Jenn! I think you’re right that referring to myself in the third person helps with objectivity – very interesting… The pandemic has probably led to a lot of people feeling stuck with their style. I know that I’m finding it harder to get dressed in nicer outfits because I do it a lot less often. It helps to have practice! I like to have color in my tops (and toppers), too, although most of my bottoms are neutrals. Adding interest with accessories is a fun way to take things up a notch. I haven’t worn my scarves in a long time, but that’s always a good way to add color and pattern.

      Wow, taking three hours to do a color analysis is a LONG time – for both you and Katrina! Color analysis CAN be a helpful tool for a lot of people, but it can also lead to challenges like both of you experienced. Sometimes I feel curious about doing a formal color analysis (I’ve never actually done that, but a few image consultants have dubbed me a Winter), especially with my hair color change. But then I worry what I would do if the person told me that all of the colors I’ve been wearing are wrong. I don’t think I would stop wearing the colors I like, but I might find others that I haven’t been wearing that might help to light me up more. I sometimes feel washed out since I transitioned my hair, and I always feel like I HAVE to wear lipstick and blush now. I’m glad both of you have discovered the colors that you most like to wear, even if it was a bit of a circuitous route. Sounds like you might be able to raid each other’s closets if you lived close by!

  7. Sdlsel says:

    Great post Debbie,I loved the evolution of blazers into ‘long jackets’, etc..  very pretty options featured. I think I have done a similar process of looking at what is in my closet and really thinking about what do I like to wear the most.  One funny aside – kimonos have been popular and I bought a bunch.  You know how many I wear – close to none!  I just find them to be a little too unstructured for me.  I have some long cardigans (like your long jackets) that have a little more structure but have to be soft and comfortable.   I do like wearing the capri and mid length pant.  If it is a short, it has to have a little length to it. Fun to read through this!  thanks for sharing.Susan

    1. Debbie Roes says:

      I’ve had the same experience with kimonos, Susan. I’ve only actually purchased one (secondhand), but I’ve tried on A LOT of them. I so often like how they look on other people, but I need more structure myself. I like a balance in terms of structure. A lot of blazers are too stiff for me now, but the kimonos are too flowing and drape-y. I mostly stick with cardigans and long jackets, but I’m intrigued by the new “shackets” that are out there. Seems like it might be the best of both worlds for those of us who like both structure and comfort.

  8. Murphy says:

    Thanks for this series, Debbie, I really enjoyed it! It’s funny – skirts were my go-to for most of my life and then one day about 5 or 6 years ago I put on a favorite tweed skirt and cashmere round neck pullover. I looked at myself in the mirror and just felt like I looked old and dumpy. So like you, I walked away from the skirts. I « archived » a few for sentimental reasons, but I only have two skirts in my closet right now – a cool leather one and a print summer skirt. I hardly ever wear them but there are occasions where they would be just right. I’m wearing pants and jeans, cropped or regular length, 98% of the time. Otherwise it’s dresses, mostly around knee length or a bit longer.
    Part of the change for me is probably my shift to more comfortable and supportive shoes. Somehow pants look better with the shoes I’m able to wear now. But somehow I just feel more like me in pants and a flattering top.

    1. Debbie Roes says:

      I’m glad you liked the series, Murphy. Thanks for sharing your skirt experience and how you’ve also transitioned more to pants, like I have. Footwear definitely can have something to do with it, as we often need to wear different shoes with skirts/dresses vs. pants (although I have a few pairs that work well with both). I think it’s important to wear clothes in which we feel like ourselves. I know that when I wear clothes that don’t feel right, it can affect my whole day. I’ve felt old and dumpy looking in the mirror in items I used to love, too. That’s a good sign that it’s time to move on.

Comments are closed.

%d bloggers like this: