I’ve Been A Fashion Editor For 12 Years And Getting Dressed Feels More Confusing Than Ever

I have no idea what to wear anymore.

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I’ve worked in fashion for well over a decade, and I know good clothes inside and out: who makes them, who wears them, and how cool, interesting people are putting them together. A big part of my job is helping others decide what pieces are worth their hard-earned money — and, of course, how to squeeze the most styling juice out of their purchases. But I also have a dirty little secret: Lately, I have absolutely no idea what to wear myself. Celebrities are pairing dresses with jeans like it is 2002 again, and influencers are hitting the runway show circuit in nearly naked outfits. And when it comes to editors like me, who have traditionally flocked to and from the same specific trends together, an elaborate buffet of TikTok-created “aesthetics” and increasingly over-the-top runway collections have left many of us confused and wondering: Which way is the style insider zeitgeist shifting?

I find myself consumed with this question one afternoon at the Bustle Digital Group offices. It’s around lunchtime and I’ve fully decided that I hate the pants I chose that morning. Despite coming from a very fancy designer label, they feel too cropped, too tailored to my waist … too something I can’t really put my finger on. As I start Google searching the style to see how the brand styled them in a lookbook instead of attending to, you know, actual work, I received an audio message from a friend who works in fashion public relations. “I’m going shopping right now because I don’t know how to get dressed anymore,” she exclaims as I sneak into a hallway to listen.

Wardrobe befuddlement is crystalizing as a theme with my contemporaries across all corners of the industry. A few months ago, WhoWhatWear co-founder Hillary Kerr posted a lengthy caption on Instagram about losing — and looking for — her personal style on Instagram, while fashion writer and journalist Lauren Sherman took to her newsletter, Lauren In The Afternoon, to explore her own evolving tastes. (“Like everything else, my style has once again changed,” she wrote. “If not completely, enough to stress me out a little.”) Just last week, WSJ Off-Duty published a package about two writers, in their 40s and 60s, relearning how to get dressed after the pandemic. And when I mention writing this article to any editor, writer, or publicist friends in passing, they laugh and sort of grimace. “Let me know what you find out,” they say.

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“I do find myself just standing in my closet being like, ‘I don't want to wear any of this, but I don’t want to get rid of it,’” Ali Pew, the fashion creative and editorial director at goop, tells me over a Zoom call. I secretly am a little relieved to know she’s been feeling stuck, too, because her clean and minimalist look has always seemed to have such a clear sense of direction unaffected by fashion’s churning trends. “I think I just always have to remind myself this is my own style and I’m always going to look better and feel better when I feel like myself versus looking at someone else.” Still, she’s found a big sticking point to be that people simply aren’t dressing for multiple occasions in a single day anymore. A flexible, hybrid work schedule has made it possible to dress aggressively down for office hours and then dial it up to the nines for an evening event. Gone are the days when throwing some lipstick and heels to elevate your jeans and blazer before leaving the office did the trick.

With the constantly looming presence of high-resolution cameras at every party, there’s also just more pressure for editors — and everyone, really — to put effort into their wardrobe. “I think the call to get really dressed is more pressing now than it was 10 years ago when you go to an event because there’s social media and there’s images,” Luisaviaroma editor-in-chief Kate Davidson tells me. With experience working at both ELLE and Harper’s Bazaar before entering the world of luxury retail, she’s seen the ebb and flow of fashion insider-approved style up close.

“About 15 years ago, the old guard [of editors] had a very specific uniform,” she continues. “It was the blazer over the shoulders, it was the perfect jeans, and the T-shirt, and heels.”

I find myself nodding in agreement, and mentally recounting the many industry-wide bandwagons I’ve jumped on for a ride. There was the “model off-duty” moment of the early 2010s — a slouchy, tissue-thin tee, skinny jeans, and a moto jacket — and the Jenna Lyons-driven J.Crew catalog look that followed shortly thereafter. (I bought a lot of striped shirts and statement pants back then.) By 2015, the style around my office moved into faded 501s and ugly sneakers (remember “normcore”?), followed by an eccentric maximalist moment ushered in by Alessandro Michele at Gucci. And, of course, there was always a constant, ongoing obsession with understated and cerebral (old) Celine under Phoebe Philo’s direction.

“[Now] I think there’s more of a look-at-me element at play,” says Véronique Hyland, ELLE’s fashion features director and the author of Dress Code, via email, when I ask for her thoughts on the industry look du jour. “I hesitate to say post-pandemic because we’re still very much in a pandemic, but post-lockdown at least, people were looking to have more fun with fashion and apply more of a special-occasion-dressing approach to all occasions.” Plus, she posits, the said “look-at-me element” is tied to the fact that the job descriptions of most editors has changed. With the rise of social media “personal brand” building, behind-the-scenes industry players are increasingly looked to as influencers as well.

“There is definitely less and less of a distinction between the two roles, in part because the job descriptions have blurred a bit,” she says. “Editors are creating social content and functioning as influencers, while influencers are stepping into newsletter writing and other kinds of more traditional media. I don’t think there’s a clear divide anymore.”

Davidson agrees. “Publishers [at magazines] are selling [editors to advertisers] against their own personal social media handles. So they’re selling that into packages and editors get bonus or some other quid pro quo,” she says. “That really tipped the scales completely toward the [idea of] editors as influencers. And as these girls all build their own personal brands, which is what we're seeing so much of now, I feel like that’s even more of a reason why they’re dressing is becoming a little bit louder, a little bit more demonstrative, and a bit more directional. We [editors] were always supposed to be behind the scenes and quiet, but that paradigm totally flipped.”

In many ways, this makes complete sense to me. There was definitely a time in my early career when I could walk into an event and tell you, just by looking at everyone’s outfits, who was the old-school writer or stylist and who had a buzzy presence online. And I’ve seen the lines fuse between categories over time: Many of my colleagues have grown their influencer side hustle into a full-time gig; top-tier digital media stars have landed contracts at legacy publications (see OG “bloggers” Bryan Boy and Margaret Zhang’s editor-in-chief appointments at Perfect Magazine and Vogue China, respectively).

Yet I still can’t shake the feeling that the answer to my quandary is less about editors wearing flashier clothes for the sake of social media, than a quiet rewriting of fashion rules. I’ve been surrounded by social media for the better part of a decade, but it’s only been lately that I feel insecure about how to dress for it. Right now the world I work in feels like a shaken-up snow globe, each little fleck of white representing a rapidly circulating trend waiting to settle into its proper place.

Part of the problem for me, admittedly, is I’m in an awkward transitional place in my life. At 35 years old, I constantly feel torn between the decade I left behind not too long ago and the one I’m hurtling toward. Trying out every “-core” look my social media feed serves me makes me feel incredibly old and try-hard, but I haven’t yet settled into an alternative uniform that I’m fully secure in committing to. Maybe I just need some space for trial and error, but with two daughters under 4 years old, I barely have time to put on clean clothes let alone rethink ways to put them together. And don’t even get me started on not wanting to dress like a mom … but also not wanting to look like I don’t acknowledge the fact that I am one.

Designer Maria McManus, whose namesake line has been a favorite of capital-F Fashion folk from pretty much day one, has also had to rethink the way she gets dressed recently. But unlike me, she feels little angst about defaulting to a few key things that work. “With my business, my husband’s business, and two kids, I've actually had to be quite thoughtful about what my uniform is, just to make getting dressed easier in the morning,” she says, calling out favorite items in her line, like a perfect-fitting pair of trousers and a double-breasted blazer. “I think it does come back to those pieces, like a great shirt, great T-shirt, a great blazer, and great pants — and then sweaters depending [on the season]. And I do stay very neutral, so everything can interchange with each other.”

On the other hand, Davidson leans into experimenting with her look. A big part of her job, after all, is putting pieces together in new ways at photoshoots — so why not reserve a few of those camera-ready ideas for herself? “Because I style [on set] so much, I kind of always have a running wish list of outfits in my head,” she says in explanation of her bold wardrobe choices, which have recently run the gamut from a low-slung pleated Miu Miu midi with boxers peaking out the top to a cut-out dress in Barbie-worthy pink. It’s a look-at-me color, in fact, that McManus has noticed more than a few other editors drawn to since debuting her latest collection.

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“It’s really interesting because we just launched Pre-Fall and there’s sort of a shot of pink ... that has really resonated. A lot of people have reposted an all pink outfit [from our lookbook] with our button-down shirt and long column sheer skirt,” she says. “It is two quite basic items, but I think your entire outfit being one color seems to be something the editors have all gravitated towards.”

Personally, I’m not sure if I’m ready to dive into head-to-toe bubblegum tones, but after reporting out this piece I’m also not about to fully rule them out as a possibility. Although everyone I spoke to for this story has a different approach to tackling style right now, they all had two things in common: a general sense that the way fashion insiders dress, much like the trends that have directed them for years, is all over the map right now — really, anything goes! — and incredibly sweet support and advice on my journey to find my fashion groove again.

So it was with an open mind that I recently found myself considering something unusual for me: a sequined Stine Goya set, picked by a colleague for a holiday party style story. “I think I want this,” I said to her as I edited the piece. “Who am I?!” Honestly, I’m still figuring out the answer to that right now. But I kind of hope she wears sparkle.