How to Dress Like You Just Stepped Out of a 90s J.Crew Catalog
Every now and then, I find myself falling down a Pinterest rabbit hole of old J.Crew catalogs from the 90s. If you know, you know. The outfits were simple, the models looked like people you’d actually want to hang out with, and everything just felt…easy. Simple. Timeless. Preppy without being stiff. Comfortable but still put together.
In the photo above, I’m wearing my favorite J.Crew Rugby Shirt, which feels so classic this time of year.
If you’ve ever wanted to look like you just walked straight out of one of those catalog pages—and as a rule of thumb, that’s been the goal for me personally for the last four years—here’s the formula I keep coming back to so you can build a capsule wardrobe of sorts.
The Shirts
Start with the classics. Think soft button-ups that look like you’ve already worn them a hundred times in the best way.
The Khakis
Forget skinny fits. Go for chinos or khakis that are a little wider, maybe even pleated if you’re feeling brave.
The Sweater
This is where the magic happens. Big fisherman knits, roll-necks, chunky crewnecks—oversized and cozy.
The Shoes
Boat shoes are the no-brainer, but you can also do loafers, bucks, or clean white sneakers.
Putting It All Together
So here’s your catalog-approved outfit:
A slightly rumpled button-up
Relaxed chinos or khakis (pleats optional, but encouraged)
A big, chunky sweater layered on top
Boat shoes or loafers to finish it off
That’s it. Simple, unfussy, and timeless.
The thing about dressing this way is it doesn’t feel like a costume. It feels approachable. Like you could be heading to class, grabbing a coffee, or leaning on the side of a sailboat in a catalog photo shoot. And honestly? Who doesn’t want to look like that?
PS: Here’s a behind the scenes look at how those old J.CREW catalogs were made