Ankle boots are a cold-weather staple that never go out of style. Whether you’re heading to work, meeting friends for a cozy coffee date, or braving the holiday hustle and bustle, a great pair of ankle boots can tie any winter outfit together.
But with so many ways to style them, figuring out how to wear ankle boots can feel overwhelming. That’s why we’ve rounded up eight chic, practical, and head-turning outfit ideas to help you make the most of your ankle boots this winter.
Trench Coat and Frayed Denim with Chunky Combat Boots
Pairing black combat-style ankle boots with frayed blue denim and a classic beige trench coat creates a look that’s edgy yet polished. The ruggedness of the boots contrasts beautifully with the structured coat, while the frayed denim adds a touch of casual cool.
A cozy knit sweater in cream or beige complements the outfit and provides warmth. This ensemble is perfect for running errands, catching up with friends, or strolling through the city on a crisp winter day. Add a simple crossbody bag and a scarf for an extra layer of chic.
Black Chelsea Boots with Leggings and a Longline Coat
Nothing beats the timeless combination of black Chelsea boots, black leggings, and a neutral-colored longline coat. This outfit is sleek, comfortable, and perfect for everyday wear. The slim silhouette of the boots and leggings elongates your legs, while the coat provides a cozy layer of warmth.
Pair this look with a turtleneck sweater underneath for added insulation. Gold hoop earrings or a minimalist necklace can elevate the look, making it suitable for casual coffee dates, shopping trips, or even working remotely at your favorite café.
Puffer Coat and Slim Pants with Practical Ankle Boots
A long puffer coat paired with slim black pants and sturdy black ankle boots is both functional and stylish. The puffer coat keeps you warm on the coldest days, while the slim pants and boots create a flattering silhouette.
For an added pop, consider accessorizing with a colorful scarf or a knit beanie to break up the monochrome tones. This look is ideal for outdoor winter activities like visiting a holiday market, running errands, or meeting friends for a casual outing. It’s the perfect mix of comfort and urban sophistication.
Oversized Sweater with Ripped Jeans and Heeled Black Boots
Heeled black ankle boots take center stage when styled with ripped skinny jeans and an oversized sweater in a neutral tone. The combination of distressed jeans and sleek boots creates an edgy yet relaxed aesthetic.
Tuck the front of the sweater slightly into the jeans for a more polished silhouette. Complete the outfit with a newsboy cap or a felt hat to add character and personality. This look is great for weekend brunch, casual evenings out, or any setting where you want to feel stylish but laid-back.
Cropped Jeans and an Olive Jacket with Mid-Heeled Brown Boots
Brown leather ankle boots with a mid-heel are a classic choice for a vintage-inspired look. Pair them with cropped blue jeans and a tailored olive-green jacket for a touch of retro glam. To keep the outfit winter-appropriate, add a bright red knit top or scarf for a pop of color and finish with a structured leather bag.
This outfit strikes the perfect balance between old-school charm and modern sophistication, making it ideal for lunch dates, exploring the city, or relaxed holiday gatherings.
Patterned Mini Skirt with Tights and Lace-Up Ankle Boots
Lace-up black ankle boots add a bit of edge to this feminine winter look, which features a patterned mini skirt and black tights. A tailored coat layered over the outfit ensures you stay warm while looking stylish.
Opt for skirts with classic patterns like plaid or houndstooth for a timeless winter vibe. A fitted sweater or turtleneck in a complementary color completes the ensemble. Perfect for festive occasions, holiday markets, or casual evenings out, this outfit is a winning combination of cozy and chic.
Sweater Dress with White Heeled Ankle Boots
White heeled ankle boots paired with an oversized sweater dress create an effortlessly elegant winter look. The crisp white boots pop against the neutral tones of the dress, making the outfit both cozy and visually striking.
Add a woven or textured handbag for extra interest, and layer with sheer tights if needed. This outfit is ideal for brunch dates, indoor gatherings, or lounging at a cozy winter retreat. For chillier days, you can top it off with a tailored wool coat in a soft neutral hue.
Cream Coat and Loose Jeans with Neutral Ankle Boots
Neutral beige ankle boots paired with loose blue jeans and a sleek cream coat create a monochromatic look that’s perfect for winter. The soft tones of the boots and coat blend seamlessly, while the relaxed fit of the jeans keeps the outfit casual yet polished.
Add a chunky knit sweater in a coordinating shade to complete the look. Minimalist accessories like a leather tote or delicate gold jewelry enhance the ensemble without overpowering it. Wear this outfit for workdays, city explorations, or sophisticated daytime events.