Looking for winter boots outfits to copy in 2025 and 2026? You’ll be obsessed with the stunning outfit ideas below, perfect for taking on cold weather in style!
Cold weather is officially here, and for most of us, that means we can hang up our tank tops and sandals, swapping them out for oversized knits and sleek leather boots. Boots are one of my favorite shoes, and depending on the style, they’re perfect for adding edge, elegance, or both to your outfit.
If you’re ready to add boots to your wardrobe but need ideas on how to style them, you’re in luck! I’ve created and curated a list of winter boots outfits, with everything from cute and casual to elegant and effortless looks. So, keep scrolling to get inspired and find your new favorite way to style winter boots.
Relaxed Yet Refined
This first outfit of mine is perfect for day-to-day wear. Pair leather boots (I love this square toe pair from Poppy Barley) with wide-leg denim and a slim-fitting cardigan. Choose a cozy neutral for your shoes and sweater to create a balanced look (the sandwich effect) then finish the outfit with a classy coat.
This scarf coat from Quince is a must for the chilly months. It’s chic, warm, and cozy.
Sweater Dress & Pointed Boots
Whether you’re going out with friends or meeting family for a fancy dinner, pointed black boots are perfect for dressing up a long, chic sweater dress.
I love the design of this dress; the simple silhouette, belted waist, and turtleneck top create a refined outfit suitable for chilly days. However, you can really use any sweater dress to recreate this look. For the boots, the pointed toe and slim heel add a feminine elegance, though you can swap them for chunky heels if you’ll be outdoors or on your feet a lot.
Bold Prints + Boots
Use heeled black boots for a bold and edgy look like the one above. Animal-print pants and a faux-fur coat pair so well with these shoes, and it’s great for a night-out look. Gold jewelry and black leather accessories are a must to finish this daring, glamorous outfit.
Chunky Heels & Wool Coats
I love a chunky heel for more of a laid-back vibe. But while these boots feel more relaxed than their slim-heeled counterparts, they still add an elevated touch to casual pieces, dressing up my classic straight-leg Levi’s jeans and a comfy half-zip from Quince.
A long, wool coat will finish the outfit and have you ready for any weather the day throws at you!
Mini Skirt & Knee Highs
The knee-high boots and mini skirt combo is truly unmatched for a flirty, feminine vibe. The rich, brown shades in this outfit are drool-worthy and add a luxurious aesthetic perfect for a winter get-together with friends or family.
Pair your mini skirt with a half-zip for a laid-back look or, if you you’re going for something a bit more refined, try a crewneck or mock neck sweater. Layer on a wool or trench coat and choose a high-quality handbag for a finishing touch.
Barrel Jeans w/ Booties
Barrel jeans are trendy and fresh, lending a modern feel to your winter boots outfits. Pair these with a slim, black blazer and brown ankle booties to sandwich the denim with elevated pieces, creating an outfit that can go from the office to a night out with ease.
Quilted Coat w/ Chelsea Boots
This is another one of my fave winter boots outfits!
My Chelsea boots from Poppy Barley are a perfect go-to for running errands or grabbing a latte before tackling all that Christmas shopping. I couple light-wash barrel leg denim with a slightly oversized turtleneck sweater for the base of this look, then layer on a quilted coat and finish with Chelsea boots for an effortlessly casual aesthetic.
Boxy Blazer + Tall Boots
Tall black boots and leggings are a classic winter duo and a versatile foundation for cold-weather outfits. A slim top and boxy blazer feel cool and casual, and work well for a monochromatic winter look.
I love this for a relaxed day spent exploring the city, and you can top the outfit off with a simple, fine knit sweater just in case!
Casual Chic Boots Outfit
Try my next outfit by using heeled boots for a simple yet sophisticated aesthetic, ideal for dinner dates, winter parties, and more.
Straight-leg jeans with a creamy cardigan feel bright and classy, while my long black wool coat, Poppy Barley heeled ankle boots, and Chanel crossbody bag add an interesting contrast and luxe finish.
Chunky Soles & Checkered Scarves
Chunky boots and a colorful checkered sweater are stunning together, and I love this look for something a bit more bold and youthful. Use neutral or monochromatic pieces throughout your outfit to ensure the vibrant scarf stands out, and don sheer black stockings to complete this edgy look.
Want something similar to this but a little more modest? Trade out the chunky-soled boots for a classic pair or swap the colored scarf for a neutral, patterned one.
Timeless, Effortless + Cozy
Pair versatile and easy-to-slip-on Chelsea boots with winter-friendly off-white jeans and a simple wool half-zip for an effortless outfit ready for school drop-offs and casual lunch dates.
I love to wear this casual look and still feel polished and put-together. The combo of simple but contrasting neutrals keeps it interesting yet classy.
Chunky Puffer w/ Knee-High Boots
Leggings are ultra-comfy in cold weather and perfect for layering, while knee-high boots and a burgundy puffer coat will definitely protect you from the elements. This look is ideal for low-temp days when you’ll be out and about.
Don’t forget to add another pop of color and layer of warmth with tall socks that match the tone of your coat!
Slim & Monochromatic
Winter boots outfits don’t have to be endless layers-on-layers and bulky pieces. You can go for something chic and form-fitting while staying toasty and comfortable in cold-weather.
Leggings are essential for a slim-fitting look, and a cute, cropped coat will help define your waist and add to the sultry appeal. Then, add tall, heeled boots to help break up the simple silhouette of your leggings and embrace classic winter style.
Leather + a Floral Midi Dress
My next outfit shows how my Quince leather bomber jacket and leather ankle boots are a match made in heaven when it comes to winter outfit ideas. These pieces are perfect for chilly weather while staying fashion-forward.
I layered them over this sleek Reformation floral midi dress(perfect way to bring summer dresses into winter) offering contrast to the rugged leather pieces and adding simple feminine charm.
Effortless Winter Vibes
Knee-high riding boots boots with a slouchy scarf jacket is the epitome of effortless elegance. This outfit feels like it took no time at all to throw together, but still has a sophisticated aesthetic.
You can opt for leggings or denim here, as long as they’ll tuck neatly into tall boots. Finish this look with an oversized tote, sunglasses, and minimalistic jewelry.
Cozy Layers & Tones
If neutrals are your vibe, go for something casual and cute and totally winter-ready with a cropped puffer coat (this Quince puffer is my fave), sleek brown ankle booties, and off-white jeans.
This outfit can be worn on repeat all winter long for something easy but classy, and I definitely recommend choosing brown boots for this look to add extra warmth and interest.
Polished in a Puffer
Tailored trousers and square-toe boots feel professional and chic, making this a must-try for a cute winter boots outfit for the office. Make sure you wear something simple, sleek, and sophisticated on top, and layer on a patterned or neutral puffer coat to stay comfy and cozy.
No matter which winter boots outfits fit your style, these ideas are sure to keep you warm, comfy, and fashionable through 2025 and into 2026!
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