Jennifer Aniston, 56, and Hailey Bieber, 29, Prove That All the Cool Girls Are Wearing Baggy Jeans This Winter

Looking back on 2025, there have been a surprising number of new denim trends, from barrel and bootcut silhouettes at the beginning of the year to a resurgence in leg-lengthening flare jeans. Going into this winter, however, celebs have been opting for a more relaxed vibe, gravitating toward baggy styles—the slouchier, the better.

For example, Jennifer Aniston was recently spotted in NYC wearing the cutest casual winter look made up of a black wool coat, beanie, and, yes, baggy blue jeans that pooled around her white sneakers. The 56-year-old actress is the latest star to embrace the slouchy style, following in the footsteps of Jennifer Lawrence and Hailey Bieber.

As a die-hard baggy jeans fan myself (I’ll never go back to suffocating styles), I couldn’t be more thrilled that the comfy-chic trend is here to stay going into 2026. Below, I rounded up five billowing pairs of jeans from Amazon to add to your winter wardrobe, starting at just $35. 

Levi’s 94 Baggy Wide-Leg Jeans

Nobody does denim like Levi’s (in fact, Aniston is a fan of the brand), so it’s no surprise that these baggy jeans tick every box. From the timeless mid-rise fit to the high-quality 100 percent cotton denim, they’re the kind of jeans you’ll wear on repeat year after year.

Cider Distressed Baggy Jeans

The distressed detailing of these ripped baggy jeans emphasizes the laidback-cool vibe of the slouchy silhouette. Style them with a cropped tee, ballet flats, and a grungy faux fur coat for a 2000s ‘It’ girl-inspired look. 

Levi’s Cinch Baggy Jeans

Another tried-and-true Levi’s style, the Cinch Baggy Jeans have a flattering high-rise fit that accentuates the waist with an adjustable fit. I love the silver metallic racing stripes on this pair (perfect for holiday outfits!), but the style also comes in basic dark, medium, and light washes.  

Trendy Queen Wide-Leg Jeans

Black jeans are a winter fashion essential, so I’m eyeing these Trendy Queen Wide-Leg Jeans that are on sale for their lowest price in 30 days. If you like your jeans to have slight stretch, this is the pair for you.

Rag & Bone Selah High-Rise Tailored Wide-Leg Jeans

For a more polished take on the baggy jeans trend, opt for this tailored dark rinse pair by Rag & Bone. These splurge-worthy jeans are ideal for dressing up for the office or a dinner out without sacrificing comfort. Simply pair them with heeled boots and a blazer for an effortlessly chic look.

By Jordan Julian