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Wondering What Shoes to Wear with Leather Pants? Here Are 5 Stylish Options to Try (& 2 to Skip)

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Shoes are often the trickiest part of an outfit to figure out, so if you’ve been wondering exactly which shoes to wear with leather pants, the trendiest winter style of the moment, you’re not the only one. Leather (and faux-leather) boots are often our go-to footwear choice for colder months, but do they make sense next to pants of the same material? Does your pant silhouette matter? What about color, or matte vs. patent finishes? Have no fear, we have all the answers for you right here. Read on for the five easiest shoe/leather pant combinations that are also incredibly chic, plus two shoe styles you’re better off saving for another outfit.

The 10 Best Shoes to Wear with Leggings, According to a Fashion Editor


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1. pointy-toe Heels Or Flats

This shoe style works with just about any leather pant silhouette (except leggings, which work better with a more substantial shoe), from cargo styles to wide-legs to classic slim-fit leather. Our favorite way to rock the duo is with a straight-leg pant and a contrasting pointy-toe kitten heel, but feel free to play around with matching shades or various heel heights.

Shop similar styles: Cuyana trench coat ($295); Everlane T-shirt ($24); Wilfred Free pants ($148; $60); Linea Paolo shoes ($120)

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2. contrasting Ankle Boots With Black Leather

Much like black leather boots, black leather pants are perhaps the easiest version of this style to wear. However, trying to pair the two together often looks either oddly incompatible and mismatched or just blah and uninspiring. Instead, try slipping a pair of contrasting boots on under your pant legs, like a gray snakeskin, khaki suede or stark white.

Shop similar styles: Nordstrom trench coat ($150; $97); J.Crew shirt ($80); Rag & Bone belt ($150); Pistola pants ($158); J.Reneé boots ($120)

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3. chunky Sneakers With Straight-leg Pants

If you’re looking for a more casual option, try pairing sporty sneakers with straight-leg leather pants. The key to making this combo work is all in the hem, which should hit just above the ankle to give a small flash of skin between your footwear and your pant leg. (P.S. If you’re rocking leather leggings, try a sleeker shoe option, like a classic Converse rather than chunky kicks, to keep your outfit’s proportions in check.)

Shop similar styles: Open Edit blazer ($75); L.L.Bean T-shirt ($25); Strathberry bag ($645); Anine Bing pants ($349); Selected Femme sneakers ($182)

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4. tall Boots With Leather Leggings

Curve-hugging leggings are a dream come true for tucking into boots that hit mid-calf or higher and, rather conveniently, the two make for an incredibly chic outfit base too. It doesn’t much matter whether you prefer ‘90s-esque knee-high boots, supermodel-inspired thigh highs or trendy lug-sole Wellies—so long as they are neatly tucked in for a smooth finish.

Shop similar styles: Only coat ($87; $61); Naadam sweater ($350; $200); Spanx leggings ($98); Chelsea Paris boots ($646)

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5. pointy-toe Kitten Heels With Culottes

We love the leg-lengthening effects of a stiletto heel, but cropped pants and high-heels rarely work well together. However, a pointy-toe kitten heel is just as good at giving us mile-long legs without throwing everything out of proportion, making them the perfect shoe to wear with this tricky-but-stylish pant silhouette.

Shop similar styles: Free People sweater ($78); Athleta sweater ($98; $70); DKNY pants ($109); Cult Gaia heels ($428)

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6. skip: Clogs

The outdoorsy nature of Birkenstocks, Crocs and other backless clog styles just don’t vibe well with high-shine leather, no matter what leg silhouette you try. Instead, pair your clogs with denim, in any wash you like, for a more compatible match.

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7. skip: Flip-flops

Leather pants work best in fall and winter (they’re far too hot to sport mid-July), so wearing them with a summer staple like flip-flops just winds up looking out of place. Swap them out for a minimalist ballet flat or loafer if you’re not into any of the suggestions above.