Figuring out your personal style can be perplexing. It can seem like some extremely stylish people — royalty, rockstars, and the like — are born with an unfailing, instantly recognizable aesthetic. But the truth is, anyone can tap into and develop their own distinct look. One way to start is to simply lean into the things you love: the well-worn blazer or animal print that’s become your “thing,” the palette you’re repeatedly drawn to, the silhouettes and fabrics that give you a little thrill. Find the never-fail elements you like wearing most; then get creative with how you use them.
For insight into how some real women live their sartorial truth, we asked a few of our consistently well-dressed colleagues what guides their specific style choices, including the one garment that’s emblematic of their current (or forever) fashion phase. The through-line: All nine women we spoke to for this series (including the three below) noted that feeling great about their appearance makes them feel great, period. So with help from J.Crew’s fall collection, we invited them to style their chosen item into a Feel-Good Look.
Jane Larkworthy, beauty editor-at-large
Style bio: Usually, I’m in clothes that are billowy and roomy, with nary a print in sight. And clogs. Almost always, a clog.
Wardrobe hero: The crazy thing about this dress is that its color kind of matches my own eye color, which, I was told, brought them out — and I’m all for anything that brings my eyes out. I love longer dresses, and I love how the fabric moves; it feels great against my legs. I used to wear dresses all the time. Someone once commented on that, “I get it. A single dress is a complete outfit. You don’t need to figure out the pieces.” I’d never thought of that, but I agree. A few years ago, pants became more of my mainstay, but slipping into a comfy dress every once in a while somehow improves my posture. Pants are slouch-worthy. In a dress, I stand taller. Other than the white rubber shoes I was wearing, I’d wear this with a pair of clogs in a dark gemstone green, or even my brown ones.
Go-to styling twists: My eyeglasses. There’s also a high probability that I’ll be wearing white, and carrying this rubber tote. It’s a street-stopper. [What makes me feel best] fashion-wise is discovering a new combination that works in a remarkable way. “What if I tried these brogues with this skirt … ? Nice!” Also, new underwear is always an exciting foundation.
Fashion feels: If I wear something that doesn’t feel like me, I tend to trip around all day — mentally, and sometimes even physically! J.Crew has always had a magical way of resurrecting a piece of clothing your dad had in college, or that your preppy friend always wore, so it could become yours. I remember when it launched — this aspirational world of 20-somethings. They picnicked, hiked, hung laundry on the clotheslines of Nantucket houses in cloudy weather. The models had beautiful partners and happy friends, and they all seemed to care about each other, and were always having such a good time. I swallowed, hook, line and sinker. I lived in their swimsuits, Bermuda shorts, and rugby shirts back in my beach house days, and my first cashmere sweater was from J.Crew.
Dayna Lee, senior designer
Style bio: No color — I only wear black and sometimes dark or light grey, which saves me so much shopping time! I mostly go with basics and rarely wear patterns or anything super-textured. A lot of my clothes and accessories are pretty versatile and pair easily with everything else in my closet; I love layering pieces. I own the most variations on a black T-shirt, turtleneck, and wide-leg pants. Fit-wise, I usually go with something more oversized or high-waisted to fit my shape better. I like my outfits to feel effortless but still look edgy in some way (e.g., something I can throw together in a few minutes but still look polished).
Wardrobe hero: I love that these rain boots are functional, but also something I can wear with everything else in my closet. They’re also very comfortable, a quality I usually go for when picking clothes. I’ll wear these on a pretty regular basis given how versatile they are, especially through fall weather (my favorite season). I absolutely love the fit of these pants and how they rest slightly above the boots to show the shape of my legs more. I’d also wear these shoes with a more fitted, high-waisted pant (cuffed); a turtleneck; and an oversized coat or a leather jacket.
Go-to styling twists: My rings and watch are definitely a signature. I always, always need to have them on, and I never really switch those up. My hair also adds to my overall personal style and adds contrast to my clothes. I’ve had the same haircut for more than five years and only play with color — it’s currently silver — which is where I get to have more variation. I also have fun with bold lip colors like gray, purple, and black.
Fashion feels: In general, I value function as much as form when it comes to clothing, but I also value minimalism and owning fewer things in general. I feel best when I’m wearing an outfit combination I’m familiar with and have worn before, though sometimes when I find new ones, that makes me feel even better. I also make sure to check the weather before I leave every day to make sure I’m wearing the right shoes, jacket, etc. A good outfit makes me feel confident and energetic, like I can really tackle anything.
Erica Smith, beauty writer
Style bio: The majority of my wardrobe is made up of pants. I have pants in every silhouette and texture imaginable and I’m currently conquering the pattern arena. They’re the starting point of most of my outfits. To make the biggest impact while wearing as few pieces of clothing as possible, I like to mix and match silhouettes, textures, colors, or patterns on top with whatever pair I gravitate toward. I’m a pretty laid-back person and while I enjoy putting things together, at the end (and beginning) of the day, I want to be comfortable and have the shortest getting-ready time I can.
Wardrobe hero: I love everything about these pants — they’re comfortable, have a fun shape, and the combo of the tailored cut and plaid pattern makes it look like I’m ready to get things done, even though I could easily lounge around or stretch in these like I would in leggings. After pants, jackets and ankle boots make up the next biggest pieces of the pie chart of what’s in my closet, so this combo is pretty on-brand for me. I’d also pair these pants with a tied-up white tee or a French-tucked oversized pullover, with chunky platforms or ankle boots depending on the chill factor outside.
Go-to styling twists: A look never feels like me until I add 1) shoes with some semblance of a lift and an interesting pattern and/or weird shape; 2) a pair of sunglasses (weather permitting) specifically picked from my collection to vibe with the look; and 3) I pile, separate, or tie my hair in the way the look intends.
Fashion feels: What makes me feel my best … Things that feel good (pieces I’d pet if I were browsing in a store). Things that fit comfortably (clothes that wouldn’t get stuck over my head during the removal process in a dressing room). And things that are supportive in some way (a huge hoodie that cradles you, or high-waisted pants that give you a nice hug). A great outfit that clicks is up there with a large cold brew as far as excellent motivators. If I have a good look on, the entire day seems to go smoother, from getting out of the door in the morning to running around to whatever meetings or appointments the day holds.
For more about what’s new at J.Crew, check out the Cut’s editor-in-chief, Stella Bugbee, in conversation with the brand’s recently instated head of women’s design, Chris Benz.
This is paid content produced for an advertiser by New York Stories. The editorial staff of The Cut did not play a role in its creation.