The Only Winter Boot Outfits to Wear in 2020

When it comes to winter boots, there are plenty of cool trends to keep your eye on as we move into 2020. In 2019, we’ve seen some major boot trends explode—from chunky platform boots and lug-sole styles to knee-high silhouettes and the wide-shaft boots that have taken over the wardrobes of fashion insiders. So what are the foolproof ways to wear them that will be chic long into the New Year?

Ahead, discover winter boot outfits that have been endorsed by the most stylish women among the fashion set. Whether you’re planning to wear them with jeans, trousers, skirt, or minidresses, we’ve rounded up the perfect outfit formulas to breathe new life into the boots sitting in your closet—or inspire you to add some fresh pairs into your wardrobe. Go on for the coolest winter boot outfit ideas for 2020.

winter-boot-outfits-282982-1573618129852-image

(Image credit: @doina)

Tuck your trousers into knee-high boots.

winter-boot-outfits-282982-1573618901115-main

(Image credit: @deborabrosa)

Here's how to wear them with an off-white knee-high version.

winter-boot-outfits-282982-1573618863910-main

(Image credit: @gosiaboy)

More evidence that tucking trousers into boots is a stylish move.

winter-boot-outfits-282982-1573618131633-image

(Image credit: @nycbambi)

Or wear them on their own with an oversize cot.

winter-boot-outfits-282982-1573618132464-image

(Image credit: @tylynnnguyen)

Thick-soled boots are the perfect pairing for tailored pants.

winter-boot-outfits-282982-1573619020493-image

(Image credit: @oursecondskin)

Wear a midi coat with sleek boots.

winter-boot-outfits-282982-1573618571610-main

(Image credit: @oumaymaboumeshouli)

Another vote in favor of this winning outfit formula.

winter-boot-outfits-282982-1573618212105-image

(Image credit: @aimeesong)

Add a patterned pair of boots to a denim look and top it off with a faux-fur coat.

winter-boot-outfits-282982-1573618771189-main

(Image credit: @louloudesaison)

Yep, animal-print boots are the perfect pairing with pants.

winter-boot-outfits-282982-1573618266287-main

(Image credit: @xeniaadonts)

Slouchy black boots are the perfect counterpoint to white jeans.

winter-boot-outfits-282982-1573618290671-main

(Image credit: @styleheroine)

Want to toughen up a minidress? Add lug-sole boots.

winter-boot-outfits-282982-1573618429804-main

(Image credit: @annelauremais)

Black ankle boots are the ultimate shoe to add to a skirt suit.

winter-boot-outfits-282982-1573618456726-main

(Image credit: @beatrice.gutu)

Same goes for a pantsuit.

winter-boot-outfits-282982-1573618503878-main

(Image credit: @thedailydeb)

More suiting inspiration right this way.

winter-boot-outfits-282982-1573618481339-main

(Image credit: @chrissyford)

A trench + jeans + ankle boots = your ultimate 2020 uniform.

winter-boot-outfits-282982-1573618678302-main

(Image credit: @jen_wonders)

Or swap in a structured blazer for another take on the previous look.

winter-boot-outfits-282982-1573618659868-main

(Image credit: @thora_valdimars)

If you're looking to dress up loungewear, this is the way to do it.

winter-boot-outfits-282982-1573618739779-main

(Image credit: @lindatol_)

Ready for the long shorts trend? Here's how to wear it like a pro.

winter-boot-outfits-282982-1573618826184-main

(Image credit: @nnennaechem)

Stick to brown tones.

winter-boot-outfits-282982-1573618960483-main

(Image credit: @estellechemouny)

If you're going for multi-hue boots, stick to a neutral palette.

Next, discover the eight shoe trends everyone will be wearing in 2020.

Explore More:
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 and runway content as well as 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, Tiffany & Co., and MyTheresa, and rising designers such as Refine and Tove, and her style has been featured in publications including Vogue.com, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on 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.