29 Comfortable J.Crew Items to Wear With Jeans and Leggings

Every single time I try something on from J.Crew, I can't get over how comfortable it is. I don't know if I just gravitate toward its most comfortable pieces or if everything they make is comfortable, but it never lets me down. And the best part is that its prices are affordable and there are tons of chic items to choose from that fit the comfort bill.
I don't know about you, but I wear jeans and leggings a lot, but girl cannot live on jeans and leggings alone, so I'm always on the lookout for cute pieces to wear with them. More often than not lately, I find them hiding in plain sight at J.Crew. And because I'm in no mood to gatekeep, I'm here to share my most recent finds with you. Each one of these comfortable items (from jackets to shoes) would pair perfectly with jeans and leggings, so scroll to shop to your comfort-loving heart's delight.
Next up, 7 simple 2023 trends that'll make your outfits so much better.

Allyson is a senior editor forBest Knockoff Luxury Clothing . She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories forBest Knockoff Luxury Clothing . Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
The 19 Luxe Nail Colors Fashion People Are Wearing Into Fall (Plus the Ones They're Quietly Retiring)
It’s time to switch your nail wardrobe.
-
I Just Got Back From Puerto Rico—Here's How Visitors Honored the Island's Heritage With Their Outfit Choices
We have to talk about Bad Bunny's Debí Tirar Más Fotos Tour.
-
The New Elite Way to Shop Is Off the Grid and Invite Only
If you know, you know.
-
Summer or Fall, This Is the Casual But Elegant Flat-Shoe Trend That Always Looks Good With Jeans
As seen on Jennifer Aniston.
-
I Just Started Investing—31 Chic Pieces That Will Have Me Dressing the Part
Effortless and elevated is the goal.
-
Spotted on Zoë Kravitz on a Stroll With Harry Styles: Fall 2025's It-Girl Denim Trend
Their style is already in sync.
-
I Shopped so You Don't Have to—the Ultimate Fashion-Editor Fall 2025 Wish List
It-girl fall has arrived.
-
The Refined Edit: 32 Luxury Finds on Sale at Saks
Starting at just $58.
-
It's Official: This Is the Flat-Shoe Trend to Wear With Fall 2025's Most Popular Legging Color
As seen in Los Angeles.
-
Editor Instincts Activated: We're Grabbing These 18 Fall Pieces Before Everyone Else Does
Run, don't walk.