We’re right on the edge of fall and winter, which means that boots are wardrobe essentials at this point. So what are the coolest ways to wear them this season? I always look to NYC fashion insiders to see which shoe silhouettes they’re buying and exactly how they’re styling them. After all, if there is one group among the fashion set who knows how to style boots best, it’s NYC girls.
Here, find inspiration for cool winter boot outfits that you’ll want to wear for the months ahead. From ensembles with jeans that are fit for the office to weekend looks you’ll want to wear on repeat to a way to wear them for a formal event, these are the freshest ways to style your boots right now. Go on to see five outfits that have a fashion-girl stamp of approval and shop pieces to try them for yourself.
Who What Wear Fashion Editor Lauren Eggertsen nails the perfect transitional look. The outfit relies on cool tailored basics that really make the python boots pop.
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For minimal, neutral-lovers you can't go wrong with a camel coat paired with knee-high boots. This outfit will simply never go out of style.
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If you have a formal evening event but want to skip the heels, swap in a pair of knee-high boots. They look especially cool underneath a sheer dress as seen in the outfit here.
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Want to wear head-to-toe black but still keep things interesting? Add some dimension to your look by tucking your pant into a pair of tall combat boots.
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When the temperatures really start to dip, you'll want to layer on a puffer coat. Just add a turtleneck, leggings, and shearling-lined boots.
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Next, discover the winter shoe trends to invest in now, according to a celebrity stylist.
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Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe TrendThey're strange, but so chic.
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My Mom Is in Her 50s and Asked Me for Fashion Advice—8 Chic Nordstrom Outfits I Put Together for Her Under $425Outdated prints and "ugly" shoes included.
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These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look CoolSee the inspiration inside.
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Click Here for Proof That This Sophisticated Shoe Color Works With Both Jeans and DressesVersatile and chic.
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This Is the Luxe Fall Shoe Trend Every Fashion Person Is Already Wearing on RepeatCount these inspo pics as proof.
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How I Let My Many Personalities Flourish This Fashion MonthHere's everything I wore, from New York to Paris.
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If You're Tired of Predictable Fall Outfits, Try This Styling Trick InsteadBold and anything but basic.
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I Live in NYC—These Are the 5 Essential Pieces I Rely On Every FallMy favorite.
