12 Fresh Ways to Wear Your Dresses With Boots

There's nothing we love more than a cozy outfit formula that will keep us warm and looking chic. One look we've learned to fall back on is dresses with tights and boots. The simple combination makes for an easy way to combine your warm-weather pieces with winter items effortlessly. With the addition of tights and ankle boots, even the floatiest slip can work under the right circumstances.

So today, we're highlighting a number of cool and fresh ways to wear your favorite dresses with tights and boots. Some work for seriously frigid temps, while others are better reserved for slightly warmer wintery weather. Still, no matter what the day may look like outside, we guarantee you'll find some easy outfit inspiration below.

Maxi Dress + Sweater + Boots

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(Image credit: The Style Stalker)

Pair a floaty floral maxi dress with a sweater and black boots. Bonus if you add some seriously cool accessories.

Floral Dress + Equestrian Boots

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(Image credit: The Style Stalker)

Equestrian-style boots add a cool contrast against a vintage-inspired floral dress.

Neutral Dress + Tights + Boots

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(Image credit: @champagnemani)

Change up your tights game and opt for a subtle but fun print to pair with a neutral dress and boots.

Minidress + Knee-High Boots

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(Image credit: The Style Stalker)

Flat knee-high boots are the perfect choice when paired with a smart minidress.

Slip Dress + Sleek Boots

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(Image credit: Edward Berthelot/Getty Images)

When it's warm, contrast a sweet slip dress with biker-style boots.

Mixed Print Dress + Ankle Boots

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(Image credit: @ada_oguntodu)

Opt for lots of cool layers in mixed prints to add interest to your boots-and-dress ensemble.

Monochrome Dress + Snakeskin Boots

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(Image credit: The Style Stalker)

A tonal look always looks so sleek and sophisticated.

Knit Dress + Chunky Boots

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(Image credit: SZYMON BRZÓSKA/ THE STYLE STALKER)

Dare to wear tights with unexpected details like polka dots or small crystals.

Blazer + Dress + Chelsea Boot

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(Image credit: Edward Berthelot/Getty Images)

Try an oversize blazer paired with a dress and a clunkier boot style for a more dressed-down combination.

Little Black Dress + Suede Boots

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(Image credit: The Style Stalker)

An all-black ensemble always looks so luxe with sumptuous tan suede boots.

Knee-High Boots + Mini Dress

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(Image credit: Edward Berthelot/Getty Images)

Knee-high boots and a pretty mini dress make for an unexpectedly cool combination.

Baby Doll Dress + Cowboy Boots

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(Image credit: Christian Vierig/Getty Images)

Colorful minis get just the right amount of contrast worn with statement cowboy boots.

Judith Jones
Senior Fashion Market Editor

Judith is the senior fashion market editor at Who What Wear and has worked in fashion for nearly a decade. Judith started on the Shop Who What Wear team, creating content and managing a team of merchandisers for the Who What Wear shopping app. She later crossed over to the editorial team, where she shares the coolest, most desirable fashion market finds and brands in her shopping-focused stories and social takeovers. She has become one of the top affiliate earners during her six plus years at Who What Wear. Before working in fashion, Judith was a TV host on the PBS travel show Globe Trekker (airing on Netflix and Amazon Prime) and shared her passion for travel and food. She studied at the prestigious London Academy of Dramatic Arts as well as Stella Adler Studio of Acting in New York. She later studied fashion merchandising and design, which laid the foundation for her career in fashion.


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