Wide-leg jeans never go out of style. Whether you prefer a boyfriend, baggy, or barrel silhouette (and the list goes on), the key is all in the fit—and how they make you feel. When you find a pair that’s both comfortable and flattering, you’ve struck gold. Hold onto them for as long as you can.
So, what do you wear them with? It’s easy to default to your usual jeans-and-cute-top combo, but as the weather cools down, layering season is officially here. That means more chances to play with textures, proportions, and pieces that make your outfits stand out.
Sure, they’re timeless, but they also dominated the Fall/Winter 2025 catwalks—making them very much of the moment in a variety of styles. At Chloé, the high-waisted pair was styled with a romantic lace blouse, a long checked overcoat, and T-bar ballet flats.
Balenciaga's had more of a baggy fit, with point-toe silver pumps peeking out from underneath the dragging hems and paired with a fluoro pink, fur-trimmed puffer jacket.
Starting to get some winter 'fit inspo? Good, because there's more to come. The street-style scene has put wide-leg denim to the test in the real world, and these are some failsafe outfit formulas you'll come back to time and time again.
With more denim and sneakers
The Canadian tuxedo is always a good idea. Denim on top, denim on bottom, you can't go wrong. Darker indigo shades are particularly trending right now. Wear with your favorite sneakers for a comfy yet stylish everyday outfit.
With a leather jacket and animal print flats
Leather and denim are a match made in heaven. Pair complementary, muted tones together, and then bring patterns into your outfit with a pair of animal print shoes.
With a statement belt and turtleneck top
The low-slung, baggy denim of the Y2K era calls for a slim, form-fitting top to offset its oversized shape. Finish the look with a statement belt buckle for some extra flair.
With a trench coat and loafers
A classic trench coat goes with everything, including your favorite wide-leg jeans. Finish off with some two-tone loafers and a silk scarf for the ultimate old Hollywood vibe.
With a chore jacket and kitten heels
Unexpected pairings, like this chore jacket and fluffy kitten heels, make for a super cool outfit. The length of the panelled, stonewash denim works perfectly with the heel height.
With a blazer and ballet flats
It doesn't get more classic than this. The easiest way to look chic and pulled together is a blazer and jeans outfit combo. This wearer has updated the look with a pair of sporty sunglasses.
Rebecca Jane Hill is the Senior Fashion Editor at Cosmopolitan UK. She has previously contributed to publications including Vogue, Elle, Marie Claire, Harper’s Bazaar, Refinery29, The Face, Glamour and Stylist. She started her own magazine, Sister, in 2012 whilst at university. Focused around feminism, fashion and culture, it went on to produce 12 globally stocked print issues, as well as countless events and partnerships. She closed the magazine in 2023.
Rebecca has been an associate lecturer at London College of Fashion since 2018, where she teaches on the Fashion Journalism course. She is a passionate second-hand shopper and is constantly on the lookout for new design talent.
















