Recently, I found myself thinking about my first-ever designer bag. I remember it perfectly: a small, beige Coach baguette decorated with the brand’s logo, gifted to me at 13 or 14 by my parents. I wore that thing everywhere despite having little need for it, but looking back, what made me love that purse wasn’t the fact that it was cute or that it went with every outfit. It was just the bag everyone else in my grade had, and I felt I needed it to fit in.
As a fashion editor, I often write about how to find your own personal style, but the truth is, it took me decades to do the same. Growing up, I was very concerned about blending in with my surroundings so, for a chunk of time, my outfits could best be described as “Staten Island Italian — Teen Edition.” Then, I was all about matchy-matchy, quirky graphic tees, and testing out celeb-approved trends — my go-to store during the mid-aughts was dELiA*s because it sold things like extra wide-leg pants and up-to-your-ribcage shorts. In college, I was heavily influenced by whomever I was dating, so my aesthetics ranged from Jersey Shore to early Zooey Deschanel.
Even when I began working in the fashion industry, I struggled to find a sense of style that truly represented me and not what I thought I was supposed to be. I splurged on clothes that I could barely afford and couldn’t quit trying to re-create whatever “It” trend I had spotted on the runway.
I’m not too sure when I made the switch, but part of finding my own personal style was by accident. For a while, I suffered from folliculitis, and I’d often wake up to hundreds of tiny pimples all over my neck, chest, and back. Panicked, I would grab a bandana or scarf in order to hide my breakout, and it soon became a styling trick I couldn’t quit. Adding that accessory to my outfits gave it some flair and also felt like a move that was unique to me. Friends and family began to associate me with bandanas; people would point them out whenever they saw someone else wearing one or give them to me as gifts. The line between wearing this piece out of necessity and wearing it intentionally became blurred, and I liked that I had my own signature look, rather than hopping on whatever was “in.”
From there, I added more “Samantha” items to my wardrobe — things that worked with every outfit I owned and made me feel good. For a while I wore metallic boots with everything, and later traded them in for a go-to white pair. I went through a period of extra-large statement earrings, which led to more whimsical fashion, such as bright colors, puff sleeves, and polka-dots. Part of finding my own personal style has also been influenced by price tags. Looking for affordable everyday clothes led me to shopping $13 Gildan sweatshirts and checkered Vans, a shoe that’s both classic and only $40.
The cumulative effect of all of that is I’ve landed on a personal style — a uniform made up of only the pieces that I seriously love, regardless of what everyone else was wearing. But I won’t say that it’s not an ongoing process. Finding your own style means evolving with it over time, and my tastes are constantly changing. Whenever I’m feeling a little lost, or my closet starts looking chaotic, I turn to a few tricks to get me back on track.
Whether you’re at step one of developing your own sense of style or just in need of a refresh, here are the rules I rely on to make sure my wardrobe is working for me.
I cover trends every single day as part of my job, and I’d be lying if I said I wasn’t tempted to shop them all. But, when I found myself searching for carrot-leg jeans last year, I had to stop and ask myself some serious questions. Was this lust, inspired by hours of looking at and talking about this questionable shape, or was it actual love? I decided that they didn’t bring me the same joy as my go-to mom jeans, so I skipped that one (and saved some money). It should be a no-brainer, but it’s important to consider what you personally like, versus what your favorite celebrities or influencers are wearing. You can always appreciate a trend from afar without forcing it into your own wardrobe or look.
Forget the “Rules”
I think a lot of finding my personal style has been reassessing what I thought I could and couldn’t wear. For instance, my whole life, I never felt like a “Dr. Martens person” because I associated those shoes with more of a rock star aesthetic. But, this past year, my white platform Chelsea boots ended up being the pair I wore with everything. You don’t have to be X, Y, Z or fit into a certain box in order to incorporate something into your wardrobe (age included!), and it doesn’t have to be a certain season or occasion to wear the items you love. If you keep looking at that one piece with a strong yearning that you just wish you ‘could’ pull it off, I’d encourage you to try it. That may be the key to unlocking a style profile that felt off-limits, but really isn’t.
Consider the Core of Your Wardrobe
Something else that really helped me develop a personal style was finding items I knew I could rely on every day, which weren’t necessarily on-trend but brought me joy. It’s how I would describe my previous relationship with bandanas, but then it became puff sleeves, ruffles, and polka-dots — people I worked with even jokingly (and lovingly) called my sense of style “Fashion Clown,” because I tended to gravitate toward pieces that featured those details and wore them all the time. Even when I style celebrity photo shoots, I can’t escape adding a white boot or sneaker — that’s my personal choice, because I think a neutral shoe looks great with everything.
Think about the versatile pieces you yourself can’t quit, then style your outfits around them. If you’re already gravitating toward Birkenstocks, don’t just save them for casual days. Pair them with dresses and jeans, or experiment by adding some socks to your look. If you love wearing button-downs, use them as sweaters, layer them under overalls, or wear them as cover-ups. Soon, these staples will become your signature pieces, aka something people immediately associate with you in a positive way.
“I would try putting things on together that were ridiculous, that totally didn’t belong together. But out of that came some amazing magic.”
Play Dress-Up With Your Own Clothes
Is there something you own and love, but you never wear because you don’t have the ‘straight off a mannequin’ ideal outfit to put it in? Maybe there’s a whole other way to wear that piece you haven’t thought of yet, and it can work with what you already own. Former stylist and TV personality Stacy London recently told InStyle she became reacquainted with her wardrobe this way. “I spent a lot of time in my closet during the pandemic, because what else was there to do? And I took it upon myself to play, to take out clothes that I haven’t worn in years — maybe they don’t fit anymore, maybe it was time to get rid of them. But also just play with what I had and experiment, go shopping in my own closet, and look at my clothes through different eyes so that I could come up with something new. I would try putting things on together that were ridiculous, that totally didn’t belong together. But out of that came some amazing magic,” she says.
Think Less About Fast Fashion
Another trick that helps me spice up my wardrobe is browsing vintage stores, or shopping secondhand sites like Etsy, The Real Real, or Depop. With so many decades worth of clothing at my fingertips, I’m much more likely to buy something that I personally love, without being influenced by hot trends of the moment. Maybe I’ll find a fun floral dress with ruffled sleeves, inspiring me to type in that search term and shop multiple options, later making that style a major part of my wardrobe (it’s happened before!). Plus, it’s a great way to embrace throwback-inspired trends while still having clothes and accessories that feel unique and special to you. Of course, you want to make sure these pieces can be worn with your staples (the green shoes you can’t stop wearing, your growing collection of chunky earrings, etc.), and that they’re items you really do love, rather than impulse purchases. But, don’t worry so much about putting a label on your style if some of what you buy feels eclectic or “punk,” while other items are more basic or “girly.” The thing about personal style is that it’s just that — personal — so if you want your thing to be old band tees styled with voluminous skirts, go ahead and do it.
The point is to choose wisely. You can buy two to three special, standout items that epitomize you rather than walking out of a mega store with 14 pieces, and end up happier and with more outfit ideas — I promise. London explained that developing your own sense of style is all about asking yourself the right questions: “How do you make your style work for you in every aspect of your life? How does it bring you joy? How does it have utility in your life and your closet? Do you feel that your closet is a place that is cohesive, or are there big holes so that it’s hard for you to wear 80% of your wardrobe, and you wear 20% of your wardrobe, 80% of the time? You want a wardrobe where you wear everything. Where you love everything.”
A few months ago, with the Y2K resurgence and my old Coach baguette bag on my mind, I went on Depop and scooped up the same design for $40. The ‘cool kids’ might not be wearing it today, but I don’t care. It reminds me of a time when I was really beginning to come into my own, and I love it more and differently now. Instead of fitting in, it helps me stand out.