When it comes to fall, we find ourselves in a strange, in-between sartorial season. There’s still that end-of-summer heat trickling into September, making the full-time transition from flowy linen pants to wide-leg jeans all the more difficult. Stacked against their more fitted counterparts, like skinny and cigarette jeans, the relaxed denim silhouette has become especially preferred for transitional dressing. You get structure from the rigidity of the denim and the comfort from its loose fit.
After selecting the top half of your outfit, however, nailing down the perfect shoe-to-jean ratio can pose a challenge amid a change in weather. As a baggy pants aficionado, I’ve discovered the key to styling shoes with wide-leg jeans: It’s all about playing with proportions. While there’s a natural gravitation to wear cropped styles with ankle boots or barrel jeans with comfy sneakers, I’ve learned that some of the best outfits come from embracing unexpected shoe pairings with my wide-leg pants—think kitten heels or ballerina pumps with ultra-baggy bottoms.
You don’t have to wait for temperatures to drop to experiment with a few fashion-forward outfit combinations. Below, we’ve compiled six stylish shoe options to wear with wide-leg jeans, along with street-style outfit inspiration for this season.
With kitten heels
PARIS, FRANCE – JANUARY 29: A guest wears long wavy medium brown hair with bangs and a center part, black oval sunglasses, metal bangle bracelets, a handheld black leather tote bag, a dark green pleated shiny jacket with a pointed collar and green button front, a black top, light blue denim wide leg jeans, black pointed toe slingback pumps shoes, outside Miss Sohee, during Paris Fashion Week – Haute Couture – Spring Summer 2026, on January 29, 2026 in Paris, France (Photo by Edward Berthelot/Getty Images)Edward Berthelot/Getty Images
Denim doesn’t always have to mean dressing down. On days when you want to look polished and put-together while staying within your comfort zone, consider taking a fresh approach with wide-leg denim and low-rise kitten heels. Lean into the casual chic look by opting for a relaxed blouse on top. No need to worry about adding structure to your outfit; the combination of baggy jeans and the sharpness of your heels will naturally create a balanced uniform. All that’s left is deciding whether to opt for open-toe or closed-toe heels.
