J.Crew Is Eating My Wallet. Here Are the 9 Things I Just Bought or Totally Want.

This is not sponsored; this is a personal obsession.

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Like so many of you, I have had an on-again, off-again relationship with J.Crew for most of my sentient life. Back in the mid-’90s, I remember poring over its catalogs, which were stuffed with cashmere cardigans in seemingly endless colors in winter and cherry-red one-piece swimsuits on sporty-chic models in summer. One of the wealthiest girls I went to high school with (and there were many) ordered barn jackets by what seemed like the dozen with a credit card she’d purloined from her parents, and that level of luxury left me dizzy with envy.

But then I didn’t think about it again for years. It was too preppy for my flared Abercrombie cargo khakis–loving heart, I thought, as I canceled the catalog.

Fast-forward to the 2010s.

Suddenly—literally overnight—it seemed impossible to not adore everything J.Crew was doing, and I didn’t even try. As someone who’d worked in the New York fashion world for years, going to the optimistic, downright accessible J.Crew presentations was a bright spot in my NYFW rounds. Everything shown was cool but democratic. A little preppy, sure, but styled in a slightly subversive way. And rules were broken. Sequins for daytime! Neon is the new neutral! Leopard-print coats for everyone! (Jenna Lyons is, and always will be, the GOAT.)

The love affair carried on for ages, but then we hit another valley, and my relationship with J.Crew cooled off. Sure, I relied on it for simple black side-tie bikinis, and yes, I owned a few pairs of slim leather sandals, but it no longer was on my radar.

And then, whilst scrolling TikTok in my CBD bath one night, a video popped up on my FYP about the newish head of women’s and kids’ design at J.Crew, Olympia Gayot. When I tell you I was too stunned to speak, I mean it. Mesmerized. I was mesmerized. And I wasn’t the only one; I noticed chatter in the Who What Wear editors’ Slack channel about how good J.Crew was again, which turned into a wildly popular article for our site.

Short story long: J.Crew is very much back and has been winning all my money this summer. Its new pre-fall pieces are just hitting stores, and there’s a lot to love. Here are a few of my favorites to kick-start your shopping spree. Have fun!

J.Crew Cropped Cashmere Crewneck Sweater ($128) in Rugby Stripe

She’s perfect. If you follow me on social, you know I bought a chunky cotton striped sweater from J.Crew a few months ago, and I’ve been wearing the heck out of it. Will that preclude me from getting this cashmere version in the green/navy stripe? No. Will it stop me from getting it in the cream/navy stripe? No. Will it stop me from getting it in the most perfect brilliant kelly green (available at a slightly more affordable $118)? No. And this is why.

I have depended on J.Crew for sweaters since 2003. Cotton, wool, or cashmere, they always offer excellent quality at a reliable price point, and they last basically forever. They are wonderful work staples that also translate perfectly to the weekend. These are perfect basics that make up the foundation of my wardrobe, and I’m excited for the new colors and stripes to join the camel, gray, and black iterations I’ve already owned for nearly two decades.

J.Crew Woven Bucket Bag in Leather and Suede ($148, plus 30% off for members) in Burnished Pecan

This bag looks about a trillion times more expensive than it is, especially in the Burnished Pecan colorway. You can definitely wear it with the crossbody strap, but I’m not going to. I’m going to remove the strap and carry this little bucket bag by its little top-handle straps because that will play up its vintage vibe. Would look equally darling with your end-of-summer white dresses as it will with your velvets and chunky sweaters come deep fall.

J.Crew Cabana Oversized Sunglasses ($30) in Cream Tort Pink

I don’t know what’s going on in the J.Crew sunglass design department, but they are destroying it right now. I picked up a pair of red cat-eye sunglasses for a very reasonable price earlier this summer that is hands down my favorite purchase of the last three months. I then tried to buy the oversize ’70s tortoiseshell aviators and was too late, so I am currently consoling myself with these big-but-glam sunnies in a creamy pink tortoiseshell. Love the proportion and the price, but I have a word of advice: Buy quickly because all the sunglasses sell out fast.

J.Crew Gwyneth Slip Skirt ($90, plus 30% off for members) in Dark Loden

This ’90s-inspired slip skirt is certainly not a new silhouette, but this iteration in the perfect army-green color is an absolute must for me for fall. I love that it lightly hints at one of my favorite movies, Great Expectations. I adore how this will look styled with a pop of red somewhere in my look (maybe the aforementioned sunglasses, maybe a shoe, maybe a matchy-matchy OPI Big Apple Red mani-pedi).

I think it runs pretty true to size, and I tend to wear either a small or a medium if I want it a little slouchier and lower on the hips. That’s the good thing about this piece; it’s super accommodating. Size up for a more effortless look; size true for a more polished look.

J.Crew Collection Cropped Lady Jacket in Suede ($798) and Mini Skirt ($350)

Don’t yell at me; I know it’s expensive. But here’s the thing. Back in the ’70s, shortly after my parents got married, my dad was sent back to Vietnam for his second tour of duty, and my mom moved to the Philippines so she could see him when he was on leave. At some point, they went to Hong Kong, and my mom had a suede skirt suit made that looks almost exactly like this. While the skirt suit is in my possession, I have a hard time wearing it because it’s so precious to me. (And also probably because the skirt is wildly short.)

So while I love getting a less precious (albeit still pricey) chance to wear this sentimental-for-me look, I realize that most folks might not want to invest so much money in a matching suede ensemble. And that’s fine! Either piece looks chic on its own; the miniskirt is just aggressively cool, especially when worn with flats or flat boots, and the jacket would look amazing with a worn-in pair of Levi’s 501 jeans.

J.Crew New Downtown Field Jacket ($178, plus 30% off for members)

Due to the aforementioned military family, I have an affinity for field jackets that borders on obsession, and frankly, J.Crew makes some of the best on the market, at any price point. I have a camo iteration from the Crew that I bought a decade ago that is still one of my most-worn and -loved pieces.

This dark moss-green cotton jacket is exactly what you want in your closet come fall. It helps your summer pieces transition into cooler weather and looks great over warmer staples too. This is my preferred piece for travel as well, as you can load up the pockets with your in-flight necessities.

J.Crew Maisie Ankle-Strap Heels ($248, plus 30% off for members) in Metallic Leather

Also available in black leather or a really excellent deep ruby leather that’s available for preorder, these shoes will surprise you with how versatile they are. They make jeans look cooler and work with cropped trousers or puddle pants, and the block heel is low enough to work for long walks and cocktail parties alike.

J.Crew Garment-Dyed Utility Mini Skirt ($60) in General Surplus

Personally, there are many styles from the early 2000s Y2K era that I lived through and never need to see or consider again. Generally speaking, anything cargo-adjacent falls into that category. But I'm going to contradict myself and make an expectation for this cotton-linen skirt with a tiny bit of stretch.

The utility detail is subtle, the lived-in fabric feels effortless, and what else am I going to wear with the 9000 striped T-shirts I own?

Birkenstock Arizona Shearling Sandals ($150) in Midnight Suede/Shearling

Currently available for preorder, this deep-navy shearling iteration of the classic Birk silhouette is just yummy. Navy always looks rich without being as stark as black, and this particular color is giving me strong luxury vibes.

As always, thank you for being here, and thank you for sticking around. If you have any questions or concerns, or want me to touch on any topics in particular, I’m all ears. Leave a comment on Hi Everyone’s Bulletin or DM me on Instagram—I’m @hillarykerr—my inbox is always open!