A few years ago, an essay titled “Why I Wear The Exact Same Thing to Work Every Day” went viral. Written by an art director named Matilda Kahl, it detailed how Kahl had spent three years wearing a weekday uniform of black trousers and white silk blouses with a neat black leather bow tied around her neck.
The story was picked up everywhere: Kahl later told Business Insider that, in the days after it was published, she was doing two TV segments, four radio interviews, and responding to dozens of newspaper inquiries a day. I was working as a fashion editor at a digital publication at the time, and I understood immediately why the idea struck a chord: Getting dressed for work is a nearly universal challenge, made doubly difficult if you’re a woman. Still, to me, the approach seemed a little extreme.
Called ”uniform dressing,” it’s an attempt to simplify this daily task by eliminating the element of choice, thereby saving the wearer the time and trouble of having to put together a new outfit every morning. It is, in Silicon Valley parlance, a means of reducing friction — a concept that has practically become gospel in recent years.
While Kahl clearly has a sense of style — that leather bow? Inspired. — the logical end of optimization in fashion isn’t a world in which everyone chooses an idiosyncratic everyday look, but rather one in which personal style ceases to exist. The idea that the perfect wardrobe is one that does away with “decision fatigue” in order to bring us one step closer to finding our inner Mark Zuckerbergs is less convincing when you consider that tech’s obsession with efficiency is also responsible for such joyless innovations as Soylent.
Still, that isn’t stopping corporations from trying to automate the messy art of self-expression: Amazon’s new styling service, Personal Shopper by Prime Wardrobe, promises to deliver clothing recommendations “curated just for you” through data gleaned from an online quiz. Like Stitch Fix, the popular online personal styling service launched in 2011, it employs both artificial intelligence and human stylists.
Elsewhere, data seems to have already won: Algorithms have so thoroughly buffed away individualism that something called an “Instagram face” exists (and you probably know without clicking what it looks like). Cities have become uncanny valleys of ads for millennial lifestyle startups, each virtually indistinguishable from the next. Everything looks nice and fine and perfectly aspirational, particularly when viewed through a screen; it also, to me, makes the idea of “uniform dressing” feel like giving in.
In the context of this pervasive sameness, personal style can be a way of pushing back, of asserting an identity beyond your productive output or the data points Facebook has collected about you.
Plus, let’s be honest — aspiring to the Steve Jobs school of getting dressed is a bit of a red flag, post-Theranos.
”I’m a strong advocate for personal style because it’s a way that you can strengthen your relationship with yourself,” says Mecca James-Williams, a stylist and contributing editor for The Zoe Report, who has dressed stars including Solange Knowles, former Georgia gubernatorial candidate Stacey Abrams, and Orange Is The New Black’s Samira Wiley. “Outside of just looking good, it’s another avenue in which you can practice self care, self love.”
Getting there isn’t always easy: Shopping can be overwhelming, proportions are often perplexing, and all of us have days where we stand in front of our closets feeling confounded by what’s inside. But a little effort now can mean way more confidence (and compliments) down the road.
Here are some tips for finding a style that works for you:
Start with basics you can build on
Peter Nguyen, a New York City-based private personal stylist for men in tech, and the founder of The Essential Man, says that even clients who aren’t especially interested in fashion usually come to him not with empty closets, but with closets full of clothes they never wear. “What I find a lot of these guys will say is, ‘You know, I thought my wardrobe was kind of boring, so I stopped by Zara or J.Crew or something, and I saw this crazy sweater and so I bought it, really hyped up, and then I got home and I had no idea how to wear it.’”
Nguyen likes to first identify the pieces they’re missing. “The way I describe it to them is: It’s like cooking, right? You want to learn the classic recipes first before you go and add your own spin and personality to it. So where I usually start with them is really building a foundation wardrobe: really timeless, versatile pieces, a lot of neutral colors, basic denim, chinos, dress shirts.”
James-Williams recommends mapping it out day by day: “I would take the process slow and think about it in terms of, ‘Okay, I wear one outfit each day. What do I need?’ Sometimes I like pants. Sometimes I like skirts. So I find four to five pieces in the pants category and the skirt category that I know I will like, and then build that up to tops.”
While “basics” will look different for everyone depending on factors like your personal preferences, profession, and gender presentation, some foolproof places to start are a great fitting pair of jeans; an everyday jacket (try a blazer, bomber, or motorcycle); non-denim trousers (think about what you like in jeans, such as a tapered leg or a slightly cropped inseam, and try pants with similar elements); and a selection of T-shirts and dressier tops that pair easily with the bottoms in your wardrobe. Even introducing one of those categories can be revelatory if you’ve been missing it.
If you’re a rookie in the fashion department, it helps to work with someone who understands fit, whether that’s a sales associate, a trusted friend, or a personal stylist. They can steer you toward pants that won’t gap when you sit and suit jackets that won’t swallow you whole. They can tell you what can easily be fixed by a tailor — a service certain retailers, including Nordstrom and Levi’s, offer for free — and what may not be worth the extra cost.
Getting a second opinion can also help you break bad habits: If you’re used to wearing your shirts two sizes too big, that’s probably what you’re going to grab from the rack. Having someone push you to at least try something new can help you see yourself in a new light. (This is basically the entire premise of Queer Eye.) Once you have the essentials down, it’s much easier to try a trend or experiment with something new when the opportunity arises.
Get rid of the dead weight in your wardrobe
The average American buys 65 new pieces of clothing per year, according to the research firm Kantar, but we spend a far smaller share of our income on the category than we used to. Because clothes have gotten so cheap, we’re encouraged to buy in greater and greater volumes — a habit that makes the experience less satisfying with every subsequent purchase, according to one theory recently posited by a Morgan Stanley analyst (and probably backed up by the pile of forgotten shirts languishing in the back of your closet). In economics, the law of diminishing marginal utility states that as consumption of a good or service increases, the marginal utility (or satisfaction) consumers derive from each additional unit declines. Or, in shopping terms: the tenth shirt we buy inevitably brings less happiness than the first.
All of this excess can make it hard to see — let alone put together — the pieces you actually want to wear.
”Sometimes you think you have all these pieces, but then when you really sit down and look, you’ll find there’s a hole, or this button doesn’t really button over your cleavage well,” says James-Williams.
A closet cleanout forces you to evaluate what actually works for you. Start by taking everything out at once, so you don’t forget about pieces lurking out of view. Then, eliminate pieces that only fit an imagined future self, are stained beyond repair, and/or are too uncomfortable to wear. Keep the workhorses of your closet — your everyday essentials — as well as anything you genuinely love to wear. And don’t, under any circumstances, put anything back in that needs to go to the dry cleaner or tailor — do that now! Or it might sit there for months. (I say this from plenty of personal experience.)
These days, depending on the quality of your unwanted items, they could even net you some extra dollars to put toward your next, more thoughtful purchase. Resale sites such as Poshmark, The RealReal, and thredUP; local consignment shops; and marketplaces like eBay all offer the chance to turn castoffs into cash. If you donate rather than going the resale route, do your research on local and national organizations (including recycling facilities) to ensure your stuff doesn’t end up among the 10.5 billion tonnes of textiles added to landfills every year.
Look for inspiration everywhere
If you have a smartphone or laptop, you have access to a world of outfit ideas. Make liberal use of Pins, saves, and bookmarks on apps like Pinterest, Instagram, YouTube, and Reddit; browse through magazines and books (old and new); and collect screencaps of stylish characters from movies and TV (Shiv Roy, anyone?). Look up from your screen, too: Take note of what stylish friends, coworkers, and strangers are wearing; visit stores you otherwise wouldn’t; walk around a new neighborhood or city and people watch.
The key, says Beth Jones, the stylist, blogger, and YouTube creator behind B. Jones Style, is “not just seeing it as something that somebody else can do, but actually thinking, ‘How can I interpret that for myself?’ Or, ‘What could I take from that and bring into my everyday life?’” It doesn’t have to be a head-to-toe outfit — it could even be an unexpected color pairing or a new-to-you silhouette.
Remember, too, that there’s a world of inspiration on Instagram beyond jet-setting influencers and celebrities — take advantage of it and follow people with different budgets, backgrounds, and body types. That way, you’re less likely to get stuck thinking that style is something only certain people can achieve.
Subreddits like r/malefashionadvice and r/femalefashionadvice have millions of members, many of whom have probably asked some of the same questions you’re wondering about. And Jones has cultivated a diverse community around her hashtag-cum-mantra #alwaysplaydressup, and says she’ll sometimes scroll through their photos when she wants to get out of a rut. Check out the tagged posts for brands you like — not just the professional photos on their feeds — and, if there’s someone on the app whose style you’re into, see if they’re following any other cool accounts you haven’t discovered yet.
Push yourself to put in a little effort
Just because you live a normal life full of Monday morning meetings, carpool pickups, and commutes doesn’t mean you have to resign yourself to an equally mundane wardrobe.
”I think a lot of it comes back to the way that we get stuck in our heads about things,” says Jones. “Like, ‘Do I have the confidence for this?’ Or, ‘I don’t have anywhere to wear this.’ Or, ‘I’m a mom with little kids. What will people think?’”
As a mom of two boys, Jones says she’s usually getting dressed for softball games or Target runs, which means putting together outfits that are comfortable but still “bring some joy and a spark to the day.” For her, that might mean colorful track pants and a fanny pack rather than Lululemon leggings and a T-shirt — anything that feels more playful and creative than the default option.
If you work in an office, a common challenge these days is striking a balance between looking professional and keeping up with the more relaxed dress codes many companies (even Goldman Sachs!) are adopting.
”I always recommend being slightly overdressed rather than underdressed,” says Nguyen. “Because you can always pull it back a little bit and wear jeans and a nice sweater — you don’t have to roll in a T-shirt and shorts even if your boss does. It’s all about where do you want to go with your career and how seriously do you want to be taken?”
”Boring office clothes” may allow one to look “professional, not special,” as The Atlantic’s Olga Khazan argued in a recent essay defending the much-maligned retail chain Ann Taylor. But they can also make a dull day even less inspiring — and they’re hardly the only option, given the proliferation of subscription rental services that allow members to try new pieces without the commitment.
Find your niche
Spend some time discovering what you’re naturally drawn to and nurture that interest. Maybe you’re a burgeoning sneakerhead, or perhaps you want to live that #cloglife. Maybe you’re into jumpsuits, zany socks, or Hawaiian shirts. This doesn’t have to be the garment or style you’ve been told “highlights” your best “assets,” and it certainly doesn’t have to be trendy. It doesn’t even necessarily have to be something you wear out of the house (case in point: caftans).
For Jones, it’s blazers: The style, she says, has the power to transform just about any outfit, whether it’s a mannish tweed version paired with a turtleneck and trousers, or one in purple leather atop an animal print skirt. “I always say, ‘Make it better with a blazer,’” says Jones. “A great, cool, classic blazer — that can be from a thrift store so easily. You can find one for, like, $5.”
Nguyen recalls working with a client in his late 30s who was into sneakers. “He owns his own business, so he’s doing a lot of investor meetings, and we built a wardrobe for him that was pretty classic — a lot of blazers and chinos and things like that. But adding those streetwear elements to that classic wardrobe makes sense for him because he’s a collector.”
Think of this as a way to get better in touch with your tastes — an approachable gateway into cultivating a style that feels uniquely “you.”
Hilary George-Parkin is a writer based in New York City. She covers fashion and consumer culture for publications including Vox, Glamour, Fashionista, and CNN. She last wrote about a shoe that’s taken over urban streets for The Highlight.