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.
Tuck your trousers into knee-high boots.
Here's how to wear them with an off-white knee-high version.
More evidence that tucking trousers into boots is a stylish move.
Or wear them on their own with an oversize cot.
Thick-soled boots are the perfect pairing for tailored pants.
Wear a midi coat with sleek boots.
Another vote in favor of this winning outfit formula.
Add a patterned pair of boots to a denim look and top it off with a faux-fur coat.
Yep, animal-print boots are the perfect pairing with pants.
Slouchy black boots are the perfect counterpoint to white jeans.
Want to toughen up a minidress? Add lug-sole boots.
Black ankle boots are the ultimate shoe to add to a skirt suit.
Same goes for a pantsuit.
More suiting inspiration right this way.
A trench + jeans + ankle boots = your ultimate 2020 uniform.
Or swap in a structured blazer for another take on the previous look.
If you're looking to dress up loungewear, this is the way to do it.
Ready for the long shorts trend? Here's how to wear it like a pro.
Stick to brown tones.
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.
-
Suddenly, All The Row-Style Girls Are Breaking This Fashion RuleAnd you should, too.
-
I Want to Build a New Wardrobe—30 Incredibly Elegant Pieces I'm Eyeing From the Nordstrom Winter SaleBring on the chic outfits.
-
I Forgot About These Winter Boots Until Meghan Markle Styled a Pair In the Most 2025 WayGood thing they're on sale.
-
I'm a Professional Shopper—These Are the 3 Best Categories From the Nordstrom Winter SaleThese chic pieces are selling out fast.
-
These 30 Incredibly Chic Picks From the Nordstrom Winter Sale Scream Cool GirlTime to up your fashion game.
-
We're Fashion Editors—Everything We Saw, Wore, Did, and Ate During NYFWLet's dive in.
-
Brace Yourself: 2025's Most Divisive Shoe Trend Has ArrivedYou'll either love it or hate it.
-
I Know You're Stylish If You Tuck Your Jeans Into Boots Like These 5 Chic WomenDon't be scared.
