6 Chic Shoes to Wear With Cropped Jeans This Winter

If there’s one denim trend that defies seasonal change, it’s cropped jeans.

Whether it’s a skinny cut that skims the ankle or a wide-leg silhouette that hits just above the ankle, this wardrobe staple has earned a permanent place in the fashion set’s rotation. As someone who wears cropped jeans year-round, switching between light washes in the summer and raw hems in the winter, I’ve found that the right shoes can make or break a look.

The perfect pair of shoes not only completes your outfit, but also sets the tone, whether you’re going for an effortless French-girl style or a relaxed, cool one. While runway shows continue to give us the perfect denim and shoe combinations, we feel like now is the perfect time to share which shoes really compliment cropped jeans.

For example, at The Row’s Fall/Winter 2024 show, minimalist ballet flats were styled with cropped denim with a slight flare. The juxtaposition of the quintessentially “feminine” flat with the casual feel of cropped jeans was a standout moment that made us rethink the style of cropped jeans. While I prefer trainers for an off-duty vibe, my fellow editors are obsessed with the timeless appeal of loafers, especially when paired with cropped straight jeans. From Miu Miu kitten heels to classic pumps Ara Carrie Bradshaw, certain shoes look beautiful with this hemline.

Beyond aesthetics, there is also a practical element. Cropped jeans are essentially made to hug the ankle, making them the perfect canvas for attention-grabbing shoes. Whether you prefer stylish, sophisticated options or something more relaxed and streetwear-inspired, balance is key. Each shoe style offers different styling possibilities. Chinky trainers add a little edge, and low heels add elegance.

Below, we’ve compiled six major shoe styles that go well with cropped jeans. With both designer and high street options, there’s something for everyone. You no longer have to worry about which shoes to pair with cropped jeans.

Shop your favorite shoes to wear with cropped jeans:

1. Ballet shoes

Style notes: Few shoe trends have seen a resurgence in recent years like ballet flats. Thanks to fashion’s obsession with quiet luxury, ballet flats are seen everywhere from the streets of Paris to the Instagram feeds of the most stylish editors. Their dainty profile pairs beautifully with cropped jeans, offering a delicate touch that balances out the more casual vibe of denim. Choose a pointed-toe style for a more elevated vibe, or a classic round-toe version for a true Parisian aesthetic. I like to pair it with slightly distressed or frayed jeans so it doesn’t look too flashy. Throw on a boxy blazer and you’re good to go.

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2. Trainer

Style notes: When it comes to casual style, cropped jeans and trainers are perfect. It adds a cool, effortless vibe that works well whether you’re running errands or meeting friends for coffee. Streetwear-inspired silhouettes with a retro aesthetic are especially popular this season, but stick to classic white trainers for a timeless style, or go for something trendier with new designs. Please try. For a sports-luxe twist, pair your trainers with raw-hem jeans and an oversized coat.

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3. Kitten heels

Style notes: Last year, the fashion world fully embraced kitten heels, and it’s easy to see why. The perfect balance of chic and comfort, they’re perfect for when you want to elevate your style without having to worry about towering stiletto heels. Cropped jeans allow dainty heels to take center stage and are the ideal footwear solution for smart-casual evening outfits. Pair it with cropped straight jeans and a tucked-in blouse for an office-ready look. On the weekend, try pairing it with a graphic T-shirt and statement belt for a cool-girl vibe.

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4. Loafers

Style notes: Loafers are very popular these days, and we think that’s because they can be styled in so many different ways. Whether you prefer a chunky sole or a sleek, slim design, cropped jeans add a polished finish without being too formal. Choose platform loafers for an edgy twist, or classic penny loafers for a more timeless vibe. I love pairing cropped wide-leg jeans with cozy knits for a relaxed yet sophisticated look.

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5. Pointed toe court shoes

Style notes: No shoe style embodies chic like the pointed-toe court shoe. Whether you choose a bold color or a sophisticated neutral, high heels elevate cropped jeans in a timeless and fashionable way. Add a pop of color by pairing bright pants with dark-wash jeans, or go monochrome with nude, black, or deep-hued pumps for a more streamlined look. Complete your look with a tailored blazer for a sophisticated look.

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6. Ankle boots

Style notes: It’s easy to pair cropped jeans with boots, especially during the change of seasons. Whether you choose sock boots for a streamlined finish or chunky combat boots for a tougher edge, cropped jeans let your boots take center stage. For a classic look, style with a pair of slim-fit ankle boots and straight-legged boots and a wool coat. If you want something more casual, opt for chunky lace-up or Chelsea boots and a leather jacket.

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