8 Winter J.Crew Outfits That'll Have Everyone Thinking "Chic!" When They See You

If you're tapped into fashion even just a tiny bit, you'll know how much fashion power J.Crew currently holds. Even as someone who never really shopped at the so-called "preppy" retailer until now, I fully understand the hype it's received this year. You can always find compliment-inducing standout pieces and easy basics you'll get plenty of wear out of. I'd even argue that you don't have to spend a penny at the store to find it helpful. How? Well, a favorite pastime of mine is looking through the outfits featured in the brand's campaign imagery and on J.Crew Creative Director Olympia Gayot's Instagram feed.

When I scroll through J.Crew's site, I create multiple outfits from the latest selection of new arrivals and best sellers. While some can be loosely re-created with the basics I already own, I'm very tempted to purchase the unique It buys, including the strappy ballet flats our team can't stop talking about and the leather bag that could totally pass as designer. 

If you're searching for fresh winter outfits, look no further. With attire for everything from the office to your winter outings, I've got it all covered. Feel free to copy each look or shop any key pieces to style them yourself. Here's to a season of stellar outfits.

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(Image credit: Courtesy of J.Crew)

With the right layers and different textures, a neutral outfit will look anything but boring. People won't know what to compliment first—the delicate ballet flats, the perfect leather bag, or the silhouette of the skirt. It's all too good.

Shop the look:

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(Image credit: Courtesy of J.Crew)

Pops of red and silver are the trendy touches the fashion set is going for currently, so why not incorporate both into your winter look?

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(Image credit: Courtesy of J.Crew)

You can never go wrong with double denim. Brown boots and a belt just add that winter-ready touch to the classic pairing.

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(Image credit: Courtesy of J.Crew)

Do you want to dress like Sofia Richie Grainge? Then this is the outfit for you. The key to jazzing up a simple white skirt and sweater is accessories, and each one included in this outfit is perfection. 

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(Image credit: Courtesy of J.Crew)

Once you get your hands on those red T-strap heels, it's over for all the other shoes in your closet. Paired with a striped sweater and a chic skirt, they make for the ideal French-inspired winter 'fit.

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(Image credit: Courtesy of J.Crew)

Workwear doesn't always have to be a simple pair of trousers and a button-down. With the help of a metallic belt and wool skirt, you'll be the best dressed in the office with this outfit. 

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(Image credit: Courtesy of J.Crew)

Keep things cool and casual for a winter weekend outing with this look. The best part has to be the ultra-cozy cashmere wrap that'll keep you feeling warm and looking chic. 

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(Image credit: Courtesy of J.Crew)

Just because you have a ton of layers on this winter, it doesn't mean you have to look frumpy. In fact, with this cardigan and leather blazer, you'll look the complete opposite. The brown bag just ties the whole look together.

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This post was published at an earlier date and has since been updated.

Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.