My Wardrobe, Myself

The intersection of clothing, emotions, and life

In my last post, I offered a suggestion for helping you increase your understanding of your style preferences. Since many of us have a better sense of what we don’t want in our lives – and in our wardrobes – than what we do want, I recommended starting there to gain some powerful insights. I also suggested looking back at what you used to love wearing but no longer do, and I explored two of my previous closet favorites that have since fallen by the wayside: skirts and blazers. I shared photos of some of those formerly loved garments, as well as examples of ensembles in which they were featured.

flared midi skirts - no longer wear

I used to love wearing skirts like this, but I don’t anymore.

In today’s essay, which is the second installment in what will now be a three-part series (I found I had more to say than I originally thought!), I look at how my style has evolved to the point where I very rarely wear skirts and blazers any longer. I’ll show how I progressed from my too formal summer “uniform” of skirts with blazers to an interim formula that better suited my lifestyle and style aesthetic. I also share my current skirt collection and my thoughts about the future of skirts in my wardrobe. The third installment in the series will cover my current style preferences and some thoughts about my future sartorial journey.

Next Generation Skirts (and Dresses) – Maxi Lengths

Once I started blogging about my wardrobe and engaging in analysis of what wasn’t working for me – and how I actually wanted to dress, I started to release my “church lady” persona. That process took a little while, but at the end of it I still liked skirts. The difference was that instead of wearing A-line, midi-length styles, I moved on to wearing the maxi-length style that had gained popularity in the mid-2010’s. During that era, I accumulated a number of maxi-length skirts and dresses, which became a key element of my summer signature style.

I fully embraced maxi skirts and dresses for about five years, and they pretty much encapsulated my summer uniform during that era, with skirts being favored over dresses due to the versatility of pairing them with various different tops. I typically only wore skirts and dresses for the duration of the warm weather season (typically July through November) back then.

Below are a few photos of my skirt and dress ensembles from that next-generation era of the mid-to-late 2010’s. These outfits do not feature toppers, but I’ll highlight some examples with “third pieces” in the next section.

maxi-length skirt and dress ensembles

I moved on to wearing maxi length skirts and dresses in 2015.

Toppers for the Maxi Skirts and Dresses

As I mentioned in my last post, I typically paired my skirts with blazers during my unintended “church lady” era. Back then, I collected both midi skirts and short blazers, as they were key components of my style aesthetic until around 2015. When I started to make my big style shift toward maxi-skirts and dresses, I paired those garments with cropped or tie cardigans instead of blazers. This created a less formal look, as well as better proportions with the longer, narrower fit of the maxi silhouette on my bottom half. Since I was no longer wearing my blazer collection at that point, I gradually started to let them go (more on this in part three).

The following are some of my ensembles featuring maxi-length skirts and dresses topped with shorter cardigans:

maxi skirts and dresses with tie and cropped cardis

I paired my maxi skirts and dresses with cropped and tied cardigans.

The Current Skirts in My Closet

At the time of this writing, I own only four skirts (including one in my “holding zone”). My remaining skirts are all maxi length, but two of them also feature a high-low element (shorter in the front and longer in the back).

Here are the four skirts that I currently own (the black and white printed one is in my holding zone):

skirts I currently own - April 2021

I only own four skirts at present and rarely wear them.

Although the above skirts are still part of my wardrobe, I almost never wear them. In fact, I only wore one of my remaining skirts last summer. Yes, it was a weird year (to say the least!), with fewer opportunities for out-and-about ensembles, but I could have worn skirts more often and decided not to. The skirt that I did wear was the black two-layer crinkly maxi skirt (second from the left). I still like wearing this skirt – and my husband also likes it, but I don’t feel as attractive in it as I used to, as my body and preferences have changed.

However, I did feel happy wearing the following outfits from 2019 and 2020, in which I paired either a drapey top or a loosely-tied cardigan with the crinkly maxi skirt:

black crinkly maxi skirt outfits

I wore these black crinkly maxi skirt outfits in 2019 and 2020. 

Will This Be the Year That I Let Go of All My Skirts?

It’s entirely possible that I may pass on all of my remaining skirts this year, or I may only hold on to the black crinkly skirt shown above. We’ll see how often I wear my skirts and more importantly, how I feel when I have them on. If I have occasions to wear my skirts this coming summer and choose not to, that will be a good sign that their time has passed. And if I purge my remaining skirts, will I buy any new ones – or will I abandon wearing skirts altogether?

I haven’t purchased a new skirt for at least a few years, as I wasn’t drawn to the styles that have been on offer. This year’s midi-length, flowing styles are more to my liking, as they’re not knee-length and flared like my “church lady” era skirts were.  Because the 2021 skirts are a bit longer and less voluminous, their silhouette lends itself to a more casual vibe that works better for my lifestyle. But skirts are not as easy to style as dresses, as I have to decide which tops to wear with them.

Since I no longer possess the super-slim waist of my pre-menopausal years, I don’t see myself wearing snug-fitting tanks or tees today. I’ve also never particularly liked tucking in my tops because I’m short-waisted, so I’ve always maintained a separate collection of tops to wear untucked with skirts. This collection has dwindled in size over the years with my body and style changes, and it’s been difficult for me to find suitable replacements. I now have just a few tops that I like to wear with skirts. This is fine if I only wear skirts occasionally, but if I buy new skirts, I might also have to purchase new tops to pair with them, and buying a bunch of new pieces isn’t exactly in line with my 2021 “less” theme.

Perhaps I just don’t need the skirts and shorter tops cross-section of my wardrobe any longer. Maybe the time for those pieces has come and gone, and I might feel relief instead than sadness if they no longer hung in my closet. Dresses are just a lot easier, even if they’re less versatile in terms of multiple outfit combinations. My life might be easier if I left skirts behind completely, and it’s possible that could be part of where my style is headed now. We’ll see what happens through the rest of this year….

Conclusion – and Your Thoughts?

I originally planned on sharing my reflections on my current style in today’s post, but since it was getting a bit long, I’ve decided to make this a three-part series. I want to get away from “marathon posts” on this blog! I’ll probably never be a minimalist in terms of my content here, but I am trying to cut down on overly lengthy essays because I value your time and attention. I also like the idea of posting more often to keep the conversation and momentum going, and some of you have mentioned that you’re enjoying the more frequent posts. My goal is to post weekly as much as possible, which has become easier to do since I started spending at least an hour a day writing about two months ago.

I’ll be back next week to talk about my current style preferences. I’ll show you photos of some of my favorite pieces, as well as some more recent outfit photos. I’ll also discuss how my style preferences continue to evolve and what I see happening with my wardrobe in the future.

So that’s a bit of the “state of the blog” and some coming attractions. Now I’d love to get your thoughts about anything I’ve shared in today’s post and in this ongoing series. Many of you weighed in after last week’s post, but I welcome any additional thoughts you’d like to add today.

12 thoughts on “What I Don’t Wear Anymore – Part Two

  1. Claudette says:

    I loved your comments in the past about eating the frog and I got the book at the library,,, I gather you are using that idea still and hence, more writing daily… I surely am enjoying your more frequent posts! and your explanation and photos of your journey into your journey… I too am short waisted but I love short pencil skirts with a top worn on outside… I haven’t worn a top inside pants/capris/skirts in years due to being short waisted…I do need longer tops with pants due to a flat bottom and find pants/capris sag out in the back after sitting in them for an hour,,, am sad that the era of skinny pants and tunic tops are ending,,, ongoing trend changes that make some people happy and others not happy!!
    yes, dresses are simpler but living in a cold winter climate i hardly wear them in winter as I am not a legging/with dresses type and will need to look for more summer ones, I am mid 70’s though and can not do sleeveless with my arms and of course sleeveless is so much available likely due to being way more cost cutting in clothing production!!!

    1. Debbie Roes says:

      Thanks for your comment, Claudette! I don’t use the “eat that frog” concept all of the time, but I really should… I always feel better when I handle the most important things first, but I still struggle with procrastination sometimes. I feel the same about the lengths of tops as you do – needing longer tops to wear with pants versus skirts. As for skinny pants, I think they are now a “classic.” They may not be on the cutting edge of fashion anymore, but I think we’ll still see lots of people wearing them and they’ll still be sold in stores (still tons of skinnies where I live). I only wear dresses in the summer, too, except on those unseasonably warm days (and it doesn’t even get cold here – I just FEEL cold more than most). You’re probably right that sleeveless dresses are more prevalent because they’re cheaper to produce, but many post-menopausal women don’t love showing their arms as much, so retailers are missing the mark (and a lot of women would probably pay more for what they truly want).

  2. NATALIE K says:

    I am new here. I found you through your old shopaholic site. I don’t believe this really fits me, but maybe it does. I’m really surprised you’re considering getting rid of an entire type of clothing but…I don’t wear anything but skirts! I do this for my beliefs, but I don’t have a problem with women who do wear pants, but it as a personal decision I made 20 years ago now. Surprisingly, I find it difficult to find floral skirts. I’m short waisted so I don’t own any dresses! Very frustrating!

    1. Debbie Roes says:

      I’ll only get rid of my skirts if I don’t end up wearing them, Natalie, and it’s possible I may buy others. I’m just pondering what’s right for me at this point in time. I’m sure that only wearing skirts makes getting dressed simpler for you, just as it’s easier for women who only wear pants (my mother fits that description). Interesting about the floral skirts… I know that dark florals have been popular for the past few years, but I guess it depends on where you are and where you’re looking. Yes, dresses are difficult to fit for those of us who are short-waisted! I have to try on quite a few to find a winner. I do better with the more streamlined silhouettes without an elastic or banded waist. I wore one dress that on which the waistband hit me wrong for a wedding three years ago and it was irritating the entire time (and I never wore the dress again).

  3. Jenn says:

    I own three skirts, two of which are leftovers from my career days and are now reserved for funerals. The other one might be more versatile, but I’ve never worn it. I can see the appeal of a maxi skirt and how it might be a more versatile choice.

    Tucked-in tops have never looked right on me either, due to my own short-waist. For that reason, and my 5’3” height, I am enjoying some of the shorter lengths in tops, though none that are cropped enough to show my belly.

    Like many others, I am also enjoying the more frequent posts.

    1. Debbie Roes says:

      I’ll definitely vouch for the longer skirts, Jenn, as well as the asymmetrical and high-low silhouettes. For some reason, they just skew less dressy (of course, the fabrication factors into that equation) and have worked better for me. As for the shorter tops that are currently being sold, that gives me hope that maybe I won’t have to stop wearing skirts. However, I ordered a few to try and they didn’t work. It’s hard to find that “sweet spot” length, and I’m very picky! Glad you’re enjoying the more frequent posts. I’m getting on a roll with it again. 🙂

  4. Vildy says:

    It’s so interesting to me to see how by switching from a flared silhouette to a narrower one you give off a willowy effect despite not having a superslim waist anymore. Food for thought for me. I need to examine my chosen silhouettes more closely.

    1. Debbie Roes says:

      To be fair, Vildy, my waist was still smaller in the earlier photos in this post (from 2015-2017), but I do feel that the narrower skirt/dress silhouettes still make me look slimmer even with a less defined waistline. It’s worthwhile to try on different proportions because it’s hard to know what will work best for us. I don’t tie my cardigans as tightly as I did before and I wear looser tops with my skirts (when I’ve worn them), but the narrower fit still works.

  5. Katrina B says:

    Gorgeous outfits, as always, and very interesting thoughts! I can’t believe I hadn’t thought of the advantage of dresses over skirts. I had just dismissed dresses completely because they are dressy. But what’s really silly is that because I have so much trouble figuring out what top to wear with a skirt, I usually wear a top in exactly the same or a very close match to the fabric of the skirt. So essentially it’s a dress. Obviously I should just switch to dresses… if I ever get tired of my skirts. I love them! Finally, after decades of too short or too puffy or too tight skirts, I realized that I only like maxi skirts and they should be fitted or slightly stretchy – no heavy gathers around the waist! I still love midi/tea length skirts but I hate looking down and seeing the masses of veins on my legs, so I don’t have any in that length anymore. Now I have five maxi skirts that I love (despite the problem with tops) and I will probably wear them until they fall to pieces.

    1. Debbie Roes says:

      Thank you for the compliment, Katrina, and I’m glad you liked this post. I used to always consider dresses to be “dressy,” too, but the maxi dresses made me reconsider that perspective (maxis were SUPER popular here for years and I still see them a fair amount). I guess you feel my pain about finding the right tops to wear with skirts! It can be frustrating, but I used to have a lot of great combinations (that I have to veer away from after my body changed). It sounds like you really know which types of skirts work for you. If I find a new “formula” for skirts that I love, I could see myself wearing them more again, but my newfound love of dresses is working for me at the moment. I hope your five maxi skirts will last for a very long time! I have the vein issue, too, so I get it…

  6. RoseAG says:

    Remembering that I”m the person who has declared she must stop buying dresses b/c I have 4 in my closet I haven’t worn yet, I think they do reduce decisions about what to wear, and make going with the “column of color” strategy easy. You look great in the photos with a dress and a contrasting sweater. Even if our waistlines are just a memory it’s always flattering to suggest they’re there, and a belt of contrasting top serves that purpose.
    I am not crazy about maxi dresses. I’m short and I feel like I look more balanced with some leg. Plus I like to wear dresses or skirts instead of shorts. I feel like a straight skirt, knee-ish length is more flattering on me than shorts, which tend to emphasis my thighs. I like the sporty vibe and long dresses don’t quite have that.

    I hope you are hanging onto those cobalt blue items, at least if you like them and they fit. I think that’s your best color.

    1. Debbie Roes says:

      I prefer to wear dresses rather than shorts, too, Rose (and I also like to wear cropped pants). Yes, I’m hanging on to my cobalt blue items, as that remains one of my favorite colors (as well as black, burgundy, and red). Thanks for your compliments about my dress outfits. I do still like to wear dresses with contrasting sweaters, and I agree that the sweater helps to define a waistline. I can see how maxi dresses would be trickier on a more petite woman, but it also sounds like you just have alternate preferences and know what works best for you (which is great). I hope you wear those four “benchwarmer” dresses soon, and I hope you decide that they’ll work out for you. Sometimes it just takes wearing something for a day – or a few hours – to determine if it’s a hit or a miss.

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