I Think My Personal Style Is Shifting

It took some time to figure out why.

On the first warm day of spring, I surveyed my closet and felt a surprising sense of uncertainty. I’d been planning to wear a casual daytime dress — historically a staple of my warm weather wardrobe — but none of the options felt quite right. I wouldn’t have thought twice about it, except for the fact that it happened again a few days later. And then again a few days after that. I found myself consistently avoiding any dresses that over-indexed on details like a super feminine print, puff sleeves, a tiered skirt, smocking, or ruffles — a real challenge, since that describes a large portion of the dresses I’ve had for years, dresses I might have once considered intrinsic to my taste. 

I’ve always felt pretty grounded in my sense of style, especially as I’ve learned to listen to my gut instincts, shopped a lot more secondhand, and really established my center in the process. It’s been interesting to observe that center moving over the last handful of months. Not drastically, but enough to throw me out of orbit, testing some of my own philosophies around how to shop (like a collector, not a buyer!), and how to build a wardrobe that lasts. 

Today’s newsletter is a dispatch from the midst of what followed, an exploration of how to navigate a shift in personal style without losing sight of what still makes it mine. 

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At first, I was skeptical. A change in taste is far from the only reason why I might be feeling stuck while getting dressed. Plus, because I was heavily pregnant last summer, this was the first time I had access to my full summer wardrobe in two years. I wanted to make sure it wasn’t just a passing mood or phase — so, I gathered evidence for months. I tried styling my dresses in a variety of ways. They felt off every time, like clothing that wasn’t the right size, even though they fit me perfectly fine. I tried experimenting with my favorite accessories, which only heightened the feeling of disconnection. The dresses seemed to compete instead of cohere. Styling them was awkward — an uneasy limbo that didn’t seem to be operating according to any particular rules, but maybe that was a good thing? I hoped by sitting in the discomfort, instead of trying to escape it, that maybe there was something it could teach me.

Some of the dresses I eventually put into storage.

Eventually, I needed some space to think more clearly. I folded up the dresses that “felt wrong” and put them in storage bins at the top of my closet. I am a big advocate of ruthlessly purging, donating, reselling, etc., but in a case like this I also thought it would be wise to give myself the opportunity to change my mind, or at least to more specifically parse what I did or didn’t like. Maybe I just needed some time away from certain pieces to feel reinvigorated about finding new ideas for styling them; or maybe, the space would provide confirmation that it was time to part ways and make more permanent room for something else.

Once I was finished packing up, four summer dresses remained: a black mini dress from Sézane, a black midi with a full skirt from Merlette, an old white Love Shack Fancy sundress with cross-back straps, and a vintage embroidered turquoise dress. Interesting. I was starting to sense some themes, but I wanted to dig a little deeper before drawing any real conclusions. I decided to use Pinterest to gather visual inspiration (a mixture of dresses from my own wardrobe that I still felt drawn to, dresses I’d been tempted to buy recently, and dresses I’d admired on other people), and then I analyzed the results.

A selection of images from my Pinterest board…

1. My full-skirted black midi dress from Merlette; 2. A 100% cotton embroidered vintage Mexican dress from my Etsy saved folder — an alternative to the similar embroidered turquoise dress I still love, but don’t reach for as often as I would if it wasn’t made of a synthetic material; 3. A striped deadstock mini dress from Rawson (there are 7 left!); 4. My old Love Shack Fancy sundress with cross-back straps; 5. Zoe Kravitz looking perfectly accessorized; 6. A still from the closing credits of The Last Days of Disco where we get the briefest glimpse of Chloë Sevigny in a strappy, striped red dress with a V-shaped drop waist; 7. A still from Jamon Jamon where Penélope Cruz wears another red dress that I haven’t been able to stop thinking about; 8. An old Dôen dress that I wish I owned — the black fabric, short hemline, and high square neck provide nice contrast to the femininity of the puff sleeves; 9. An outfit shared by Laura Vidrequin, who has incredible style and writes this wonderful Substack; 10. My black cotton mini dress from Sézane, which is still in very limited stock; 11. A vintage silk turquoise dress I’ve been eyeing.

And some analysis…

I dove headfirst into the cottagecore / milkmaid aesthetic when it exploded in 2019, and many (if not most) of my summer day dresses are from that time period. The mood board above marks a shift away from the midi-length, floral print, pastel, puff-sleeved styles that defined that era, toward something more streamlined and adaptable. Not because cottagecore isn’t trendy anymore — it hasn’t been for a while — but because of something more fundamental: I think I’ve reached a point where I’m conscious of wanting my individual styling to dictate the terms of how I look, rather than a hero item or recognizable trend. Even though that sentiment extends to my entire wardrobe, I can see why dresses in particular had become a sticking point. Unlike separates, dresses don’t offer as much room for nuanced styling, and the overpowering aesthetic of most of my cottagecore-era dresses only amplifies this limitation. That doesn’t mean dresses are off the table for me — I just need to be thoughtful about choosing pieces that allow my style to speak louder than the clothes themselves.

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I recently bought the vintage embroidered dress and striped deadstock dress pictured above, and I’m happy to report that I’ve been wearing both with enthusiastic frequency. I’m tempted by this very simple black cotton midi dress from Everlane with rave customer reviews, but holding off for now in case I can find a secondhand option I like just as much or better. I’ve also been gradually donating and reselling some of my old dresses — it’s time for them to spark joy in new homes.

I hesitated to write about this since I feel like there’s still more to figure out, but I’ve found a lot of value in the process itself, and I’m hoping others might, too —

1. Identifying that a true shift is, in fact, taking place (vs. a temporary mood).

2. Embracing the awkward stage that occurred while trying to re-style pieces that weren’t clicking.

3. “Merchandising” my closet by putting some stuff in storage.

4. Making a mood board to visually map out the direction in which I feel like my style is shifting.

5. Pinpointing the precise nature of the shift, and confirming that current trends aren’t the motivation behind it.

6. Thoughtfully investing in a couple new-to-me items, and donating or reselling stuff that no longer feels right.

In my early twenties, I probably would have run straight to Zara to buy a bunch of cheap stuff before even taking the time to understand what was going on. Now, I’m trying to be intentional about my approach, and I think it’s paying off. I promise I’ll keep you posted — and in the meantime, I’d love to hear about your own experiences navigating tangible shifts in personal style. How did you identify that one was happening, and what did you do about it — if anything?

xo Harling

Graphics by Paige Stewart Enslow.