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.
Cashmere sweaters that are this affordable don't come around every day.
Next up, 7 simple 2023 trends that'll make your outfits so much better.
Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. 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.
-
Step Aside, Leopard Print—This Is Unquestionably 2025's It Print
Alaïa and Zara both agree.
By Anna LaPlaca
-
Madewell's Insiders Event Sale Is So Good—27 Picks Chic People Will Be Adding to Their Carts
Get 25% off just about everything.
By Jennifer Camp Forbes
-
Well-Dressed Celebs Have Basically Stopped Wearing These 3 Shoe Styles With Leggings
Find out which five styles they're into.
By Allyson Payer
-
I'm in Awe Over How Chic the New J.Crew Collection Is—29 Items That Will Have Fashion People in a Frenzy
Stunning. Absolutely stunning.
By Bobby Schuessler
-
These $20 Old Navy Flats Are Just as Chic as the $900 Pair I Have Been Coveting Since Last Spring
These are guaranteed to sell out.
By Jennifer Camp Forbes
-
These Are the 7 Stylish Shoe Trends Fashion People Will Be Wearing With Jeans This Spring
I see chic denim outfits in your future.
By Jennifer Camp Forbes
-
If You Have Great Taste, You Don't Want to Miss These 30 Chic J.Crew and Madewell Sale Picks
So many gems. So little time.
By Jennifer Camp Forbes
-
25 Spring Staples I'm Replacing My Old Ones With From J.Crew's Massive Sale
Wardrobe reset (at a discount).
By Michelle Scanga