6 Chic Shoes to Wear With Cropped Jeans This Winter

If there’s one denim trend that seems to defy the seasonal shuffle, it’s cropped jeans.

Whether an ankle-grazing skinny cut or a wide-leg silhouette that hovers just above the ankle, this wardrobe staple has earned a permanent spot in the fashion set’s rotation. As someone who lives in cropped jeans year-round—switching between lighter washes for summer and raw hems for winter—I’ve come to realise that the right pair of shoes can make or break the look.

The perfect shoe not only completes an outfit but sets the tone—no matter if you’re aiming for effortless French-girl style or laid-back cool. And with runway shows continuing to serve us impeccable denim and shoe combinations, now feels like the right time to share which shoes truly complement cropped jeans best.

Take, for example, The Row‘s autumn/winter 2024 show, where minimalist ballet flats were styled with slightly flared cropped denim. The juxtaposition of the typically “feminine” flat with the casual feel of cropped jeans was a standout moment that inspired me to rethink how I style my cropped jeans. Whilst I lean towards trainers for a more off-duty vibe, my fellow editors are devoted to the timeless appeal of loafers—especially when paired with cropped straight-leg jeans. From kitten heels at Miu Miu to classic pumps à la Carrie Bradshaw, certain footwear works beautifully with this hemline.

Beyond aesthetics, there’s also a practical element at play. Cropped jeans, by nature, frame the ankle, making them the perfect canvas for shoes that command attention. Whether you prefer sleek, polished options or something more laid-back and streetwear-inspired, the key is balance. Each shoe style lends itself to different styling possibilities; chinky trainers add a bit of an edge whilst a low heel imparts elegance.