How to Wear Mid-Calf Boots

Of all the boot styles out there, mid-calf options can be one of the most daunting to wear. The edge of the boot typically hits between the ankle and knee, making it hard to decipher exactly which dress lengths and jeans will complement the look.

To get to the bottom of this, we’ve drawn inspiration from chic celebrities and street-style stars on how to style the boots — plus rounded up some must-know tips for choosing the right fit and silhouette. Below, discover everything you need to know, and shop a range of chic mid-calf boots perfect for elevating your wardrobe.

1. Choose boots that fit comfortably around the calves.

Boots that are too narrow in the calf will be uncomfortable, while boots with lots of excess room can actually make your calves look bigger (a major con if you have wider calves and struggle to make them look slimmer). The key to achieving the perfect fit is finding a pair that hugs your calves and ankles without it feeling constricting. To test this, try wedging your finger between your calf and the back of the boot. If your finger fits there without any gaps on either side, the boots should be wearable (and not require much breaking in). You can also look for styles with zippers or elastic at the back for extra flexibility. If you’re into a more laidback style, try a cowboy boot.

2. Opt for a heeled pair to make your legs look longer.

Shorter ladies, listen up. To elongate your frame, opt for a heeled pair. The style looks amazing in practically any heel height, from a sexy stiletto a la Kim Kardashian to a modern kitten heel for greater walkability.

3. Pair them with a knee-length skirt.

While mid-calf boots work with many skirt lengths, we love the idea of pairing them with a knee-length skirt or dress — as this creates a svelte effect.

Sam Edelman Calexa Sock Bootie - $103

4. Or try a shorter skirt for a sassier look.

For a slightly less covered-up aesthetic, mid-calf boots also look stunning when paired with a miniskirt.

5. Style with cropped jeans. 

Follow Rosie Huntington-Whiteley’s lead by pairing your mid-calf boots with cropped jeans (note: a high-waisted pair can offer an even more flattering effect). For this look, it’s best if the hem of your pants hits the top of the boot to avoid awkward gaps.

6. Pair them with skinny jeans for a lengthening effect.

Even if your jeans aren’t cropped, they’ll work with mid-calf boots, especially if they’re form-fitting. Tuck a pair of skinny jeans or leather leggings into your mid-calf boots to create a streamlined effect. Bonus points if you style the jeans with sock booties, which will add to the sleek look.

All products featured have been independently selected and curated by our editorial team. If you buy something through the links included on our site, FN may earn a commission.

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