There are some outfits you never forget. In a perfect world, you remember the good ones. The ones that gave you confidence (I’m looking at you, double denim), the ones that make you feel like the best version of yourself (the magic jumpsuit I wear to 80% of the black tie events I attend). But as with so many other aspects of life, I’ve learned more from my style failures than my successes.
Take for instance, my family’s trip to the Final Four in 2019. We were incredibly lucky to get to watch the University of Virginia play (and eventually beat) Texas Tech for the national championship. I was there with my husband and two of our kids as well as my dad, my brother, and two of his kids. Everyone was decked out in their orange and blue and I felt like I needed to do that, too. I’m a UVa. alum who owns one UVA sweatshirt, so I wore that, and I borrowed a baseball cap from someone (or maybe I bought one?). I wanted to look the part of sportsball fan for this special event.
But here’s the thing: I’m not a sportsball fan. I was uncomfortable and self-conscious all night.
I felt like I was wearing someone else’s skin. I know that’s a bit dramatic, but it was a big epiphany for me. It doesn’t feel good to project an image that doesn’t jive with who you are.
A friend of mine expressed the same sartorial sadness via text just a few months ago.
On the surface, fashion can feel, well, superficial. But getting dressed is a creative act and a form of self-care. And just as your style can make you feel balanced and confident, a lack of it — or a costume trunk approach to it — can erode your confidence and make you feel out of whack and insecure.
After four years of working from home, I am struggling to be more intentional about what I wear and how I wear it. So sitting down to write this was pretty selfish. I wanted to pull all my thoughts together in one place. So here’s what I did to try to jumpstart my personal style.
It all starts with a closet cleanout.
Curate your closet
I’ve mentioned stylist’s Allison Bornstein’s AB Closet Editing System before, but I’ll go into a bit more detail here because I think it’s a fabulous approach to this intimidating chore. Without even knowing you or seeing your closet I can say one thing for certain: You own too much clothing. I do, too. We all do. Using this system helps solve for that by making every item in your closet earn its place, but it only works if you pull out everything and look at each item really critically. No cheating. Remove every single thing.
This is going to take a while. So grab a beer or a glass of wine and queue up a fun playlist. Also, make sure you’ve got a full-length mirror nearby.
Pull out the Regulars. These are the items of clothing you wear the most often — your greatest hits. Set these aside in a spot you can easily access — maybe on your bed.
Identify the Nevers. This pile will probably look pretty different from the Regulars. You may already be running out of room on your bed, so maybe the Nevers go on the dining room table, in a guest room, or some other seldom-used space. For me, the Nevers are usually either prints or things I bought while traveling. (What is it about being in a different city that makes me think I should be a different person?!)
Divide the Nevers pile into three more piles.
Pile #1 is the No, Never pile These are things you’re going to get rid of. Stuff that doesn’t fit, stuff that you no longer like or stuff that no longer gives you confidence. Sell the good stuff at a consignment shop. Donate the rest.
Pile #2 is the Not Now pile These are the things you’re not ready to part with, but shouldn’t take up space in your closet. These items are not in your regular wardrobe rotation: occasion wear, maternity clothes, your favorite pair of jeans that you’re sure will fit again once you figure out hormone replacement therapy. Put them in a guest room closet, a suitcase in the basement, a SKUBB from IKEA that you can slide under your bed — anywhere but your closet, where they become the trees preventing you from seeing the style forest.
Pile #3 is The How pile These are things you love in theory, but don’t wear because you don’t know how to style them. Keep these in the same room as your Regulars pile.
Experiment with the Regulars and the Hows. This part’s tricky. And time-consuming, but it’s really important. You need to figure out how to combine the Hows with the Regulars. Collecting inspiration and naming your Three Words (two concepts we’ll get to soon) will help. Watch the video I shared above, too.
Organize your closet as you start putting stuff back in it. This may require some trial and error and a lot of this discussion is outside the scope of this piece, but for the purposes of what we’re talking about here, I strongly suggest organizing your closet by clothing type (blazers together, sweaters together, pants together) and then by color (black blazers, navy blazers, grey blazers). It doesn’t have to be complicated and it doesn’t have to be gorgeous.
Keep in mind what KC Davis says in her book, Keeping House While Drowning: “I love a calming visual as much as the next person, but it’s important to remember that not everything has to be aesthetically pleasing to be organized and not everything aesthetically pleasing is functional!”
Record lessons learned. This is my tip, not Bornstein’s. You’ll learn a lot about your shopping and style habits as you edit your closet. Open a note on your phone or a Google Doc and record those observations.
Here’s what I learned when I cleaned out my closet last weekend: I take too many chances on final site items I find on the web. Sometimes it pays off. But all too often, buying something I didn’t try on and can’t return ends up being a mistake (shocker, I know!). I also tend to love the idea of prints, give in to temptation and buy them, but then never wear them. My husband even pointed this out to me when he watched me try on a printed wrap dress last summer. Being the stubborn person that I am, I bought the dress anyway — and then consigned it before the year was over. (See “Understand the difference between taste and style” below.)
Rinse and repeat. This isn’t a one-time thing. You should do a closet edit every time you switch out clothes for the season, anytime dressing has begun to feel like a chore, and whenever you find yourself thinking, “I don’t have anything to wear.” Bullshit. Yes, you do. As Bornstein often says, “You don’t need more clothes. You need more ideas.”
Name your three words
The Three-Word Method is an editing tool of sorts — another gem from Alison Bornstein. It gives you a framework that helps you decide what to hold onto and what to let go of, sartorially speaking. It will help you, as Bornstein says, “access, accentuate and amplify” the details of your personal style.
The idea is to find three words to describe your style. Keep in mind that there’s supposed to be a little tension among these words. The first word is a practical word: It’s defined by your Regulars. This word should describe your current style. The second word is an aspirational word. A North Star of sorts. And the third word should provide what Bornstein calls “an emotional counterpoint.” It should describe how you want to feel in your clothes.
It helps to see some examples. Bornstein’s words, for instance, are 1970s + classic + elegant. Here are some other examples from her book, Wear It Well, which I wholeheartedly recommend:
Jane Birkin: tomboy + sexy + casual
Princess Diana: sporty + demure + opulent
Rhinnna: Sexy + tough + sporty
Michelle Obama: bold + daring + polished
Not every piece of clothing needs to match all three words. Think, rather, about the totality of your wardrobe. “We rarely think of the clothes we wear as a holistic entity,” explains Bornstein, “so these systems are designed to bring your style into alignment, create a wardrobe that makes you feel good, and cultivate the image you want to project into the world … ”
Still confused? Here’s a helpful illustration. Lots of women have a blue-and-whtie striped button down. But they might style it in completely different ways depending on their three words:
While I might wear mine tucked into Levi’s with a blazer and gold jewelry, Sofia Coppola might wear hers with trousers and ballet flats,” writes Bornstein. “Phoebe Philo might wear hers oversized and untucked. And Kim Kardashian might wear hers over a sleek catsuit. This striped shirt can work for each of us, but how we each make it sing is where our Three Words come into play — and where style is created.
Find your foundations
Quick: Think of someone you know who has great style. Have you ever noticed how consistent their outfits are? They have a foundation, and they build on it. Basically, they wear a lot of repeats. They futz with the foundation (changing the shoes, swapping the jewelry), but they build an outfit using the same blocks, over and over. Leandre Medine Cohen, formerly of Man Repeller currently of The Cereal Aisle, calls this the uniform template. To help you figure out what yours is, she asks, “What is the most surefire outfit you have in your closet — the one you put on when you’re in a rush, want to know you’ll look good (or at least like yourself!) and don’t have time to think about what you’re wearing?”
My uniform template is jeans and a blazer. In the winter I might add boots to the base. In the summer, the blazer is linen and the shoes are sandals. Yours might be a wide-leg trouser and a button-up shirt. Bornstein calls these a base and talks about them a lot. “Outfit repeating is actually a sign of someone who is confident and knows their style,” she explains.
Collect inspiration
But Bornstein doesn’t want you to go out and buy more clothes. She wants you to shop your own closet. “You don’t need more clothes,” writes Bornstein. “You need more ideas.” All kinds of creative types collect ideas for inspiration to iterate on. They call it a “swipe file.” Create your own and fill it with examples you love. I have one in Photos and another one on Instagram. If you subscribe to print magazines or love to peruse catalogs, you could fill a folder with paper clippings or cover a bulletin board with them.
The idea isn’t to copy and paste whatever you see onto yourself, or to create a shopping list based on what an influencer is peddling: The idea is to get your creative juices flowing and then shop your own closet. Here’s how Bornstein explains it.
Understand the difference between taste and style
Becky Malinsky, formerly the fashion editor at the Wall Street Journal and currently at 5 Things You Should Buy, wrote a great column about this last year. Here’s how she breaks it down:
Consider our taste as our kingdom in taxonomic rank, and our style as our individual, VERY specific species. Or in simpler terms, taste is a general category in which things you love fall into. But not everything you love needs to be something you buy, own or wear. Not everything you love will suit you. Style is more specific. It’s the things you love, that you wear (and don’t wear you) and make you feel confident and distinct.
You guys, this is incredibly liberating. When I realized that I could love a piece of clothing or a pair of shoes — that I could think it was gorgeous and simply appreciate it — while simultaneously realizing it didn’t make sense for me, everything changed. And I’m not alone. “It’s my taste, but it’s not my style,” is a mantra you should repeat more often than you add something to your cart.
Shop for your life, not special events
You don’t want a closet full of things that are perfect for a specific event, location or situation, you want a closet full of things that are perfect for you. So don’t shop for weddings, black-tie occasions or big work events when you need to, buy occasion wear when you find something you love.
Bornstein recently tackled this quandary on Instagram. Let’s say that you were invited to a destination wedding in Tulum. It’s tempting to shop for a dress for a wedding in Mexico, but if you do that, you’re just cosplaying as a woman going to a wedding in Mexico instead of showing up as yourself. The same goes for dressing like a sportsball fan or Square Dance Barbie. Pretending to be someone else doesn’t feel good — which means it won’t look good either.
I’ve made this mistake plenty of times. Exhibit A: this fun red velvet blazer and matching pants from the Gap on the top of my Never pile in the photo below. I thought it would be a great outfit for a Christmas party. It fits well. It looks good on me. Only one problem: it isn’t me.
Experiment
Developing a sense of style involves a lot of practice as well as trial and error. It doesn’t just happen and it’s not just a matter of buying stuff. You have to practice. You have to experiment. And while you’re doing that, keep in mind what Amy Smilovic, founder and creative director for Tibi explains, “There is no right or wrong, there is only you or not you.”
Also, you don’t have to practice in public. Conduct your style experiments at home if that’s more comfortable. Build on your base, try out the wrong shoe theory, or commit to the 75 Hard Style Challenge (style’s answer to Dry January/75 Hard/Whole30) if the discipline of it all appeals to you.
Follow smart stylists
I recommend these people as resources not because of their personal style, but because of their philosophies regarding style. They’re smart and thoughtful about it all.
I obviously relied very heavily on Allison Bornstein for this piece. That’s because, in my opinion, she’s creating the most practical and helpful style content out there. I also like the fact that she doesn’t focus on shopping, but on styling what you already own. Follow her on Insta, TikTok and YouTube. Also, buy her book.
Follow Amy Smilovic of Tibi on Insta and at
on SubstackTibi offers a Style Class via Instagram Live every Wednesday. It can get pretty heady pretty quickly, but I always pick up a nugget or two of style wisdom when I watch (even though I don’t buy anything they recommend).
Leandre Medine Cohen ( on Insta and at
on Substack) and Becky Malinsky (on Insta and at on Substack) are generally way too wacky for me, but I enjoy their thoughtfulness and they certainly embrace experimentation.Meghan Alida Strachan, founder and CEO of Dorsey, has exquisite, expensive taste. But you don’t have to buy the products she links to — just swipe the ideas. Follow her on Insta and at
.Meredith Peck’s get-ready-with-me videos on Insta are mesmerizing. Her style is a bit over-the-top for me, but I still get lots of ideas from it.
And, finally, if you haven’t listened to this episode of the Ezra Klein show, it’s worth it. It doesn’t focus on fashion, but it’s definitely fashion adjacent.
Now, go edit your closet.
Have a great weekend,