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Chelsea boots are a closet MVP.
This type of boot is ready for anything, from patio brunches with friends to rainy commutes. They’re stylish, durable, and the perfect fit for all seasons—but deciding what to wear with them can be tricky.
If you have a pair collecting dust in your wardrobe, we’ll help you learn how to style Chelsea boots. Our 10 standout outfit ideas can spark your creativity, and we’ll also let you know which Chelseas are our top picks. When it’s time to shop, browse ThredUp to find preloved Chelsea boots at affordable prices.
Chelsea boots are ankle-high, round-toe boots designed with elastic side panels. They date back to the Victorian era and were among some of the first footwear to slide on and off easily.
The name “Chelsea” was first linked to these boots in the 1950s and 1960s. This is because the boots became popular in London’s Chelsea neighborhood, a trendy spot known for its culture and arts scene. Celebrities like David Bowie and The Beatles wore the boots out and about, contributing to their popularity.
Chelseas became emblematic of the punk scene in the 1970s and have continued to be an iconic look since then—but now, they’re a must-have in a wide range of fashion genres. This forever fall season trend is versatile and comfortable, a true classic worth adding to your closet.
Here are our 10 best suggestions for styling Chelseas with specific types of pants, dresses, and skirts.
Wear Chelsea boots and skinny jeans for a casual but elevated look. Tuck skinny denim into the boots (or a pair of boot socks, first) and add a knit sweater or cardigan. Chelsea boots are top winter boots for women and look great with a longline coat.
If your skinny jeans are too long, roll them before you put the boots on. If they’re too short, this outfit looks great with a small gap between the bottom of your jeans and the boots.
![Alt text: A woman wearing wide-leg jeans with Chelsea boots.]](https://cdn.prod.website-files.com/66902b0c958b1f38e1fdbb1c/6744f1aaee4239745f18cc87_AD_4nXdgwj_AHkR0Gpy6QjS9kfPnP4NgeiejZiltUdr29wR-v72kjksZKhKXiICSoajiSVP7XEtfW-2O-_H5O-rO0qr7jplxvclKTeI3u5MIclQ1jbDgWcPdxwIeApkNJJ8edQvu6sZ54A.jpeg)
Chelsea boots are just one type of shoes that work well with wide-leg pants. For the best effect, make sure the hem of your jeans falls over the boots so your legs look longer. Pair this with a fitted top or tuck in your favorite blouse for a balanced silhouette.
Straight-leg jeans are just as classic as Chelsea boots, and together, they’re a winning outfit. Choose a slim pair of jeans—you want the bottoms to slide right into the shoes—or reach for a cropped style instead if you prefer space between the shoes and the pants. Add a crewneck sweater for a fall picnic or lunch dare, or try a T-shirt instead if you’re wearing this outfit in spring.
Chelsea boots look sporty and laid-back with slim-fit joggers. Style these sweatpants and boots in winter with a fitted T-shirt and puffer jacket. In warmer weather, opt for a T-shirt and denim jacket. This relaxed ensemble is ideal for a casual night in with friends or running errands.
A sweater dress is an excellent Chelsea boot outfit for fall or winter. On colder days, wear this combination with opaque tights and a chunky scarf, and if it’s warmer, lose the tights and swap the scarf for a lightweight option. This outfit works for the office with a trench coat or out with friends with a bomber jacket. It’s a chic way to dress up Chelsea boots without sacrificing comfort.
Wear a mini skirt with tights, Chelsea boots, and a light leather jacket in summer. This look is ideal for a date night or a concert if you’re feeling edgy. Add a crossbody bag and head out the door.
A midi skirt is great for transitioning from summer to fall because you can wear it with a simple tank top or layer up to stay warm. Anything goes—pleated, flared, or straight—but we recommend a flowy skirt with suede Chelsea boots and a tucked-in sweater.
Tailored pants let you take Chelsea boots to the office. The pants’ clean lines complement the boots’ sleek silhouette for a sophisticated end result you can wear to a meeting in fall or winter. Choose neutral colors, like black, white, or gray, and add a fitted blazer for workwear that’s anything but boring.
Flare jeans and Chelsea boots create a retro-inspired outfit. The jeans' wide leg opening covers the boot shaft for a streamlined look that can be worn dressy or relaxed. Add a blouse for a casual Friday at work or a striped sweater for dinner with friends.
For a monochrome look, style black jeans with black Chelsea boots and a black shirt. Reach for skinny jeans or try this look with straight-leg denim and a cozy sweater. To elevate the outfit, add a statement belt.
From budget-friendly finds to waterproof options, here’s a round-up of our favorite Chelsea boots.
The leather Duchess Chelsea Boots by Thursday Boot Company are available in various colors, like black coffee, walnut, and amber wheat. These stylish, durable shoes have a fully lined, glove leather interior for maximum comfort, plus antimicrobial shock-absorbing insoles. The outsoles are studded for added traction, ideal for being out and about in icy weather conditions, and there’s flexible elastic goring.
These leather Chelsea boots are handcrafted in small batches from high-quality materials. You can choose from models with a low or slightly elevated heel. If you don’t like leather, grab them in suede instead.
H&M’s budget-friendly boots are an excellent way to get on the Chelsea boot trend without breaking the bank. They’re made with a classic silhouette, including elastic side panels and a pull-on tab, and the soles are stylishly chunky.
The H&M Chelsea Boots look great with everything from dresses to denim, and the low heel makes them practical for all-day wear. They’re available in black, brown, and beige, with a satin lining, and are made of polyurethane and thermoplastic rubber.
The waterproof ONA AVE Chelsea boots from Sorel are highly versatile. Wear them in rain or snow with leggings, denim, and dresses, and you’ll stay dry and look great.
The ONA AVE boots are made of waterproof full-grain leather or suede and are available in black, gray, plum, tan, and honey white. They have a heel pull tab for easy on and off and a chunky FEATHERGRIP™ rubber outsole for excellent traction on slippery surfaces.
This Chelsea boot is ideal for running errands and activities like hiking in fall and winter.
The Blundstone brand is synonymous with comfort and durability, and that holds true when it comes to their Classic Chelseas. These shoes are long-lasting (many people have owned theirs for years) and made of water-resistant leather or suede. There’s a shock-absorbing footbed—perfect for long days on your feet—and the roomy toe box keeps your feet cozy without feeling cramped.
Blundstone’s Chelsea boots are available in black and shades of brown. If you choose a leather pair, the material softens over time, molding to your foot. Additional highlights include a Washable Comfort Lite footbed, heat-resistant outsole, and polyurethane midsole.
These Chelsea boots from Cole Haan are a more elegant option, ideal for outings where you need to look put together. The Greenwich Chelsea Bootie, available in black, oat, madeira, and golden toffee, is entirely waterproof. It features a back pull tab, double elastic gores, a cushioned midsole, and a rubber lug outsole. This boot is handcrafted and lightweight, with responsive cushioning for your feet. You can wear a pair year-round to dinners and events, but these really shine on rainy fall days.
Shop these Chelsea boots on ThredUp for less.
Chelsea boots open up endless style opportunities across seasons and occasions. Whether you’re wearing boots with jeans and a jacket for winter or rocking them with a skirt in summer, Chelsea boots are a versatile nod to ’50s–’70s fashion that’s still trendy today.
If you’re ready to find the perfect pair, ThredUp has an extensive collection of affordable Chelsea boots in many brands, sizes, and styles. You can also shop for garments to wear with the shoes—50,000 new arrivals drop in our online thrift store daily, and everything is preloved at an affordable price.
ThredUp’s AI-powered Style Chat and Improved Search features make finding outfit inspiration and building unique looks easy. Browse our platform today for everything you need to create stylish outfits with Chelsea boots.
