As summer winds down and autumn approaches, one silver lining is the return of denim to our daily wardrobes. Besides sandals, it’s time to swap in shoes that are better suited for cooler temperatures. As the clouds roll in and the breeze picks up, we’ll be trading open-toe styles for more practical options.
Luckily, there’s no shortage of stylish shoes to choose from, as verified by the Fall/Winter 2025 runways held waaay back in February. We might not have thought about them in months, but the time has finally come when they are more relevant than ever. And frankly, we could not be more ready.
If you are too, you can’t go wrong with one of the below jeans and closed-toe shoes outfit combos that effortlessly nail transseasonal dressing and offer a fresh take on denim for the new season. Don’t just take our word for it, check them out for yourself…
High-waist jeans and ballet flats
Victoria Beckham famously declared in her 2006 fashion manual (titled That Extra Half an Inch and now only available to buy on eBay) that wearing skinny jeans with ballet flats would leave you looking like your legs were golf clubs. Either way, it’s certainly a dated look, and we recommend pairing your pumps with a more modern, high-waisted, straight-cut silhouette for a laid-back, cool girl style.
Cuffed jeans and socks + loafers
We hate to take sides, but when it comes to the generational sock culture war, we’re firmly in the high-socks camp—especially when worn with loafers. Opt for cuffed jeans (or, ya know, just turn up the hems on your favorite pair) to ensure your style statement takes center stage.
Frayed hems and kitten heels
Slingback kitten heels have prim and proper connotations, so we love the idea of pairing them with distressed denim. Whether you opt for subtle clashing with frayed hems or go full grunge with rips and holes, it’s a guaranteed sartorial slay.
Skinny jeans and cowboy boots
Skinny jeans weren’t exactly “of the moment” for a while, but the tucked-in trend provides the perfect opportunity for you to grab yours out from the back of your wardrobe. If you swore never to return to the skin-tight silhouette, you can still get in on this look with any slim or narrow leg jeans—or, just allow for bunching at the tops of your knee-high boots.
Wide-leg jeans and animal print shoes
Animal print isn’t going anywhere this fall! After cow print burst onto the scene in spring, it’s set to return as a stylish contender alongside leopard spots, zebra stripes, and snake print. Rather than making this the focal point of your outfit, rely on the voluminous hems of your wide-leg jeans to offer just a peek of pattern.
Ankle-grazer jeans and Mary Janes
We love a preppy Mary Jane! If you struggle to keep ballet flats on your feet, the signature strap on this shoe is a game-changer and deserves to be recognized as so with a pair of ankle-grazing jeans to show off its sleek silhouette.
Alexandria Dale is the Digital Fashion Writer at Cosmopolitan UK. Covering everything from the celebrity style moments worth knowing about to the latest fashion news, there’s nothing she loves more than finding a high street dupe of a must-have designer item. As well as discovering new brands, she’s passionate about sustainable fashion and establishing the trends that are actually worth investing in. Having worked in fashion journalism for six years, she has experience at both digital and print publications including Glamour and Ok!
