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.
The shoe that will make all your outfits feel like a billion bucks.
I’m going on a ski trip soon and need this for my snow-bunny-by-the-fire-drinking hot-chocolate transformation.
Give everyone at your office holiday party something to talk about!
There is a LOT of burgundy on this list. You’ve been warned!
I love chocolate brown for basics.
This sweater with the brown turtleneck peeking out of the top… just sayin'!
I like my beanies to feel a little elevated, and the brushed cashmere here does the trick.
I’ve been dreaming of a pair of slouchy corduroys for winter, and these are it.
Amazing.
Ultra cozy and ultra chic with a loafer.
I love how often this skirt was styled with an oversize sweater on the website.
I find tops so hard to buy mainly because it takes a lot to catch my eye, and this stopped me in my tracks.
One of J.Crew’s pricier items, but this jacket is moment-defining.
All of my favorite styling on the site involved this sweater.
C-H-I-C.
The frenzy this dress sends me into has me feeling like it's Christmas morning.
Just gorgeous.
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.)
Another tulle top I simply have to have.
The brushed cashmere beanie might be lonely without its friend, the brushed woven scarf.
A good button-up will last forever.
The sweetest little dress-up bag.
I simply can’t get over the lining peeking out of the bottom of this skirt.
I stand firmly behind the colorful-opaque-tight trend.
I’ve been drawn to white loafers lately and am particularly fond of this ruched pair.
This is the outfit Gayot wore in the try-on I mentioned, and the cardigan will be mine.
J.Crew has been getting it so right with the early 2000s nostalgia looks that it’s a little hard for me to take.
Jeans you can wear from infinity to beyond.
This is an accessory I’m always regretful I don’t have when the holiday parties roll around.
I have this and wear it multiple times a week. I especially like it with a white T-shirt peeking out up top.
