How To Wear All Your Booties This Winter

We are well aware of the fact that we're going to be hard-pressed to get you to wear anything but booties this winter. While we're long-time fans of the whole socks-and-sandals thing (it's not easy to say no to a pair of loafers, either), we know that boots are the cold-weather go-to for both styling and practicality purposes. By now, you've probably racked up a few different types: The trusty black ones, the bold lace-up option, a Chelsea boot, and maybe a metallic number or two. So why not come up with some fresh new ways to wear them?

The five outfits ahead are all comfortable and trend-forward, making the boots feel more like statement-makers than a wear everyday pick. And don't worry: We're not saying you can't wear them every day; what we are saying is that we can all get a little more creative with our styling this year (love you, jeans and sweaters, but we've gotta break out of that uniform sooner or later). Click on for some ways to do just that — we swear you'll never look at your booties the same way again.
1 of 5
If you've decided to embrace the bold kitten-heel bootie trend we've spotted all over Instagram, why not go bold with the rest of your outfit, too? To avoid feeling too fancy (because shiny metallic shoes can have you feeling just that) dress them down with a distressed pair of jeans and a fashion hoodie. Finish the look with an eye-catching puffer (the brighter, the better) and some simple hoop earrings. This look checks all the boxes: casual, cool, and perfectly unexpected.

Topshop Oversized Puffer Jacket, $93, available at Topshop; Zara Laminated Heel Ankle Boots, $69.90, available at Zara; R13 Alison Cropped Straight Leg Jeans, $425 $162, available at Moda Operandi; Catbird Dream Silver Earrings, $50, available at Net-A-Porter; Gucci Embroidered Hooded Sweatshirt, $2,600, available at Gucci.
Advertisement
2 of 5
With a heeled lace-up bootie in a bold hue, jeans aren't the only option. Try a print-mixing, dress-over-pants look that coordinates just so. Top things off with some more neutral outfit-finishers, like a warm (and sleek!) double-breasted coat and a practical, hands-free crossbody.

ByFar Lada Leather Red, $370, available at ByFar; Zara Cropped Check Trousers, $49.90, available at Zara; A.P.C. Irene Floral Print Silk Shirtdress, $406, available at MatchesFashion; Ganni Fenn Coat, $350 $297.99, available at Need Supply Co.; ASOS Glamorous Velvet Cross Body Bag, $34, available at ASOS.
3 of 5
— PAID —

TBH, we can never have enough little black booties. Take the go-to shoe up a notch this winter and opt for a perforated pair that will stay with you through spring. Try styling them with elevated staples — like a frayed-hem midi-skirt, ribbed turtleneck, and fur-collared jacket. The result is a polished (and cozy) look that translates from the office to cocktail hour without any sort of quick change.
4 of 5
We've already proclaimed our love for this sequin turtleneck. Style your Chelsea booties with this festive top and some cropped flares, then layer a graphic sweatshirt on top to make it feel a bit more digestible for daytime. Accessorize with a luxe box bag and you've got an all-black look that's anything but boring.

Balenciaga Button-embellished Leather Chelsea Boots, $1,015, available at Barneys New York; Mango Flare Trumpet Jeans, $50, available at Mango; H&M Sequined Top, $39.99, available at H&M; & Other Stories Geometric Embroidered Sweater, $85, available at & Other Stories; Ximena Kavalekas Caterina Black Shiny, $1,650, available at Ximena Kavalekas.
5 of 5
Pair a combat boot with an unexpected floral midi skirt (throwing some tights in the mix if you need them). On top, it's all about a conversation-starter tee and a warm down jacket. Allow some delicate gold jewelry to tie the outfit together, and you're hitting multiple trends in one simple look.

Warehouse Dandy Mono Skirt, $80, available at Warehouse; Doc Martens Zip Pascal Aunt Sally, $140, available at Doc Martens; Bagatiba Rose Necklace, $320, available at Bagatiba; Uniqlo Women U Lightweight Down Jacket, $49.90, available at Uniqlo; The Wing New York Woman Shirt, $40, available at The Wing.
Advertisement

Shop your inbox!

yay! get ready for the good stuff!