There are two types of people when September hits: those mourning their sundresses and flip-flops, and those (like me) already mentally layering cardigans over shirts and jackets. Autumnal dressing offers numerous styling opportunities. Think: rich textures, cozy layers, and, most importantly, endless excuses to dust off your favorite boots for the colder months ahead.
Though if the sudden appearance of winter garments all over your social feeds and shop windows feels like a personal attack, don’t worry. These six jeans-and-boots outfit combos (and how to wear them) are here to help you romanticize the seasonal shift instead of resisting it.
Boots bring structure to an outfit, while denim keeps things grounded and wearable—aka a pairing that works for everything from casual office days to after-dinner drinks. So if you're still crying over the temperature drop, grab a PSL and let me, your Cosmo style fairy godmother, help you plan some chic fall outfits.
Patent points + a cuffed style
Pointed patent leather boots instantly add a sleek, edgy touch, while cuffed jeans keep the overall vibe elevated yet casual. It’s the ultimate high-low mix—perfect for everything from desk to dancefloor. Go bold in double denim, and bring in extra depth with accessories that add color and texture, like statement orange sunnies, a woven bag, and oversized silver earrings.
Timberlands + baggy fit
Yes, the much-loved Timbs are making a round in the fashion scene, and they’re bringing that retro, street style energy. Try them with slouchy jeans and an oversized blazer, but juxtapose the loose silhouette with a fitted tee and Carrie Bradshaw-esque handbag. This is the ultimate early aughts outfit recipe, brought bang up-to-date for 2025.
Snakeskin + straight leg
Move over, leopard print, because snakeskin is taking the lead. These bold boots make a statement, so let them shine by pairing them with classic straight-leg jeans like Levi's 501s, a crisp white tee, and your go-to long trench coat. It's the perfect look for transitional weather.
Western suede + bootcut
Understated cowboy boots in rich suede are packed with vintage vibes, especially when poking out from underneath a pair of bootcut flares. Extra style points if you match it with a tonal jacket and large framed sunglasses, mastering that ’70s Western mood.
Stiletto + barrel leg
This one’s for the fashion girlies. The utilitarian shape of barrel-leg jeans contrasts perfectly with glam, stiletto-heeled boots, elevating your whole outfit with minimal effort. Jump on the barn jacket trend if you haven’t already, and layer like a pro with an oversized white shirt.
Biker + light wash
Biker boots can feel heavy, but pairing them with a light-wash jean softens the get-up instantly. It's also our duty to inform you that tucking your jeans into your boots (whatever the style) is so back for fall/winter 2025. A bomber jacket and aviator shades keep the biker look on point, but consider adding a chunky sweater depending on how chilly it is.
