The Boot Outfits That Are All Over NYC

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.


A blazer + button-down + black jeans + python boots
(Image credit: @laurenegg)

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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Camel coat + white bag + white boots
(Image credit: @laurencaruso_)

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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Blazer + sheer dress + knee-high boots
(Image credit: @oursecondskin)

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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Blazer + tee + baggy jeans + combat boots
(Image credit: @nycbambi)

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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Puffer coat + turtleneck + leggings + shearling boots
(Image credit: @chrissyford)

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.

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.