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Fall boots bridge the gap between warm-weather style and cold-season practicality. You want footwear that handles cooler temperatures, shifting weather and longer days on your feet without sacrificing polish. From ankle boots to taller silhouettes, the right pair supports your wardrobe through changing layers, varied textures and the return of everyday routines.
These fall and Chelsea boots are ready to warm up your wardrobe this year without freezing your bank balance.
Pull-on boots have a tendency to fit snuggly, but these lug sole boots are a winner with a variety of sizes, including wide-sized options, colors and prices. The boot features an elasticated gore to allow freedom of movement when worn for long hours. Chelsea boots have a down-to-earth energy that’s fantastic for any look.
The imitation suede is long-wearing and ideal for those chilly days when the ground is a little cold or wet. It’s a classic, affordable addition to your fall wardrobe.
Not all fall boots are short anklets, and this tall boot is perfect to match long maxi skirts and for that country estate look when worn over tights. It’s available in black or brown, with plain or rhinestone finishes available.
The little extra blink will light up dreary wintery days. The square toe and chunky heel are sure to keep your feet comfortable if you’re running around.
Whether it’s rain, sleet or damp ground from melted snow, these boots will keep you walking confidently as you putter about the garden or race your dogs at the park. The flexible PVC material is comfortable and keeps your feet dry.
The chunky sole features anti-slip lines, and it’s available in several colors and a few half-sizes for a perfect fit. Match it over your jeans or cause a stir with a maxi skirt.
Combat boots are always a favorite, but the plaid lining of these is a winner for a softer, more feminine look. The rounded toe ensures comfort, and the grippy sole will keep you steady on any terrain, whether you’re adventuring with friends or hopping out at the grocery store.
The boots are available in four shades, two with plaid lining, and in the most common sizes, including half-sizes. However, if you have larger feet, you may struggle to find the right size.
No need to hit the alpine slopes to wear these fashionable mid-calf boots. They are ideal for cold days, with a quality faux-fur lining and Thinsulate Insulation, and the waterproof upper keeps your toes toasty and dry.
It’s available in white or gray and features a bungee lace-up, and the well-gripped soles provide support on slippery surfaces like iced parking lots. Unfortunately, there are limited sizes available, so if you are well over six feet tall and have larger footsies, you’ll have to keep looking.
These classic Chelsea anklets are a quick fit with the zipper design — slip them on and head out. While the thin sole may require you to avoid stepping in puddles, the cushioned interior keeps you comfortable while shopping or lounging at home. It’s available in several colors and half-sizes for wider feet.
Partner these with a relaxed slack suit or skinny jeans for an understated look that’s undeniably feminine. The faux-fur interior is cozy and will keep you from getting cold feet.
Step out in style with these typical Western boots with pull-up tabs. The foot section is quite narrow, so ensure you get a shoe horn to help you pull on the heel without jamming your fingers. Size up if you have a wider foot or prefer a looser fit. Choose from white, black, red and several shades of brown in synthetic rubber for easy maintenance.
These are ideal for work, fun and vintage fashion. Wear them with jeans, short A-line dresses with pleats, skirts or longer midi dresses.
If you work in a cold area and struggle with cold toes, these genuine suede platform mini boots are perfect. The memory foam insole is lightweight, and the pull-on tab makes slipping into the faux-fur interior easy.
These boots are perfect for wider feet, as they are available in half-sizes and in extra-wide fits to ensure premium comfort. Match them with lounge wear at home or jeans and winter corduroy pants for a relaxed look indoors and outdoors.
If you love stitching and a classic finish, these Chelsea boots are enduring in quality and potential. The lug sole and rounded toes ensure comfort and foot health. The elastic gore allows the ankle to move, and the pull-tab helps you fit these boots. It’s available in black, brown, dark brown and khaki colors in various sizes and half-sizes.
The durable soles are anti-slip, which is a must for rainy or freeze-thaw days when balance is a fickle friend. Wear them to work, parties, outings and clubs.
If you love boots but detest socks, these elastic top, wide platform Chelseas are perfect. The elastic side panels are warm and keep your ankle as comfortable and warm as your feet. The chunky heel and elevated soles will keep you dry, while the rugged sole has enough grip to keep you on your feet in any weather.
They are available in nuede suede, black PU and black suede with half-sizes for improved fit. Wear them with pants, mini skirts or midi dresses and rock the “rebel” look while keeping it classy.
Make the most of your knees with these fall boots. While long boots are traditionally winter wear, the elegant, sheer finish works well with tights, jeans, miniskirts and more. The slinky zipper helps you fit these boots comfortably, while the synthetic suede helps keep cold wind off your legs without hiding them in long pants.
The chunky heel improves comfort and balance, while the increased insulation keeps the leg part up without adding thickness or wrinkling. They are available in various sizes and half-sizes and several shades of brown, white and black.
The cushioned footbed and soft lining offer comfort and warmth, while the stylish, classy motorbike design with bold buckles makes a fashion statement. Match them with an oversized sweater and tights or tuck them under a maxi skirt for dramatic flair.
The grippy soles offer stability over rough or slippery terrain, and you can get the optimal fit with the range of sizes and half-sizes. It’s available in brown and black, and the inside zipper helps with fitment.
If you abhor heels, this flat-soled Chelsea is perfect for comfort and autumn warmth. The soft fleece lining complements the genuine suede outer and rubber sole that keeps it dry on snowy days. The pull tab helps your fit, while the elastic gore lets your foot enjoy some freedom.
It’s available in full and half sizes and five colors. They’re a perfect match for ripped-bottom jeans, a dress or leggings for a casual look.
Skechers is synonymous with comfort, and these Chelsea-style anklets are must-have fashion pieces. The black, mushroom or chocolate-tone boots are made from synthetic leather, so they’re waterproof, while the outer zip and inner elastic gore make them a dream to put on.
The pull tab helps with slipping your heel in, while the air-cooled memory foam sole keeps your feet happy, even if you’re running around all day. Wear this with anything.
Learn how to style your Chelsea boots with the pros:
Ankle boots top the list. They work with jeans, dresses and skirts, making them easy to wear from early fall through cooler weeks.
Leather and suede are popular, but treated or waterproof finishes better handle light rain and temperature changes.
Aim for a snug fit with a little room in the toe box so heavier socks don’t make the boots feel tight or restrictive.
Fall boots put your whole look together. One strong pair can carry you from crisp mornings to long evenings without missing a beat. Choose styles that feel good, work hard and still look sharp. When the boots are right, getting dressed stops being a chore and starts feeling fun again.
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