I’ve written before about my love for J.Crew. I frequently think about how a J.Crew cashmere hoodie I stole from a guy friend in 2009 single-handedly made me appreciate the timelessness of a well-made sweater. I’ve been wearing the brand since my first middle school camping trip, but ever since Olympia Gayot came on the scene as creative director in 2020, my friends and I can’t get enough. She’s also responsible for relaunching J.Crew’s iconic catalog, which is something I was GIDDY about.
If you don’t know Gayot’s Instagram, well, you should. Each season, she does try-ons of her favorite new J.Crew pieces, styling them in ways so enviable that it came up in conversation at lunch with two of my friends this week; the most memorable being the way she recently put together a red cashmere sweater-and-shorts set. This is all to say I, and everyone I know, will have whatever she’s having. And you should have it, too, which is why I’ve narrowed down 30 of my favorite fashionable J.Crew looks (largely curated from the Olympia’s Picks tab—you’re welcome for the tip) below.
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Teagan T-Strap Heels in Patent Leather
The shoe that will make all your outfits feel like a billion bucks.
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Jacquard-Print Sherpa Half-Zip Fleece Pullover
I’m going on a ski trip soon and need this for my snow-bunny-by-the-fire-drinking hot-chocolate transformation.
Christopher John Rogers X J.Crew
Front-Slit Skirt in Red Vinyl
Give everyone at your office holiday party something to talk about!
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Delaney Kickout Sweater Pant
There is a LOT of burgundy on this list. You’ve been warned!
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Tissue Crepe Turtleneck
I love chocolate brown for basics.
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Cashmere Diamond Fair Isle Sweater
This sweater with the brown turtleneck peeking out of the top… just sayin’!
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Brushed Cashmere Beanie
I like my beanies to feel a little elevated, and the brushed cashmere here does the trick.
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Loose Straight Corduroy Pant
I’ve been dreaming of a pair of slouchy corduroys for winter, and these are it.
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Lace-Trim Slip Dress in Textured Satin
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Ultracozy Trouser Socks
Ultra cozy and ultra chic with a loafer.
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Gwen Lace-Trim Slip Skirt in Textured Satin
I love how often this skirt was styled with an oversize sweater on the website.
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Tulle Button-Up Shirt With Lace-Trim Camisole
I find tops so hard to buy mainly because it takes a lot to catch my eye, and this stopped me in my tracks.
Christopher John Rogers X J.crew
Barn Jacket in Gold Lamé
One of J.Crew’s pricier items, but this jacket is moment-defining.
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Cashmere Relaxed Cropped V-Neck Sweater
All of my favorite styling on the site involved this sweater.
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Stratus Lace-Trim Pant in Textured Satin
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Collection Velvet Dress in Cherry Print
The frenzy this dress sends me into has me feeling like it’s Christmas morning.
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Made-In-Italy Colette Satin Slingback Heels With Pearls
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Wrap Trench Coat in Italian Double-Faced Wool Blend
This coat is near identical to the one Ali MacGraw wears in Love Story. (If you don’t know the movie, it’s essential fashion viewing.)
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Collection Sheer Bra Top
Another tulle top I simply have to have.
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Brushed Woven Scarf
The brushed cashmere beanie might be lonely without its friend, the brushed woven scarf.
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Étienne Oversized Shirt in Striped Cotton Poplin
A good button-up will last forever.
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Collection Small Bow Bag in Satin
The sweetest little dress-up bag.
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Chiffon-Lined Sequin Skirt
I simply can’t get over the lining peeking out of the bottom of this skirt.
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Control-Top Opaque Tights
I stand firmly behind the colorful-opaque-tight trend.
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Maison Ruched Loafers in Leather
I’ve been drawn to white loafers lately and am particularly fond of this ruched pair.
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Featherweight Cashmere Pointelle Shrunken Cardigan Sweater
This is the outfit Gayot wore in the try-on I mentioned, and the cardigan will be mine.
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Pleated Organza Mini Skirt
J.Crew has been getting it so right with the early 2000s nostalgia looks that it’s a little hard for me to take.
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Mid-Rise Straight Jean in 1984 Rigid
Jeans you can wear from infinity to beyond.
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Velvet Bow Hair Clip
This is an accessory I’m always regretful I don’t have when the holiday parties roll around.
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Cashmere Relaxed Crewneck Sweater
I have this and wear it multiple times a week. I especially like it with a white T-shirt peeking out up top.
