What makes a Chelsea boot? The most notable features include a tight ankle fit, stretch gusset sides and pull tabs. Intended to be snug all around your feet, offering a reliably functional shoe for the season with the right amount of fashion. These days, Chelsea boots appear in many iterations, finishings, materials, and colors.

For the fall/winter 2021 season, I’ve pulled together the most comfortable, functional, and fitting for constant wear. Reach for these all season long to keep your feet warm and protected from all the elements in your area. Sizing recommendations are included next to each style to help you make an informed purchasing decision.

One more thing to keep in mind - they’re supposed to be fitted, so don’t be discouraged at first when trying some of these on if they fit too snug; they’ll stretch over time.

Disclosure: Some of these items are affiliate links and I earn a small commission if you chose to purchase through the links. This article was updated January 11, 2022.

Loeffler Randall

BRIDGET CHELSEA COMBAT BOOT

A polished Chelsea boot that doubles as a winter dress shoe. Slip-on with ease thanks to the elastic side gore which acts as form and function in this urban boot. Pair with a kick crop jean and your favorite tweed blazer for a smart casual, polished look. Take your standard size. 

Shown in Brown (more colors) | $395 at zappos.com

Rachel Comey

BARLA CHELSEA BOOT

A winter white boot with a rubber platform sole and leather upper that works with kick crop pants and dresses. Thanks to the elastic shaft these are versatile, comfortable, and cool. Take your standard size, if in between sizes, then size up.

Shown in White | $495 at garmentory.com

Gianvito Rossi

Chester Calf-Hair Chelsea Boots

Animal print lovers rejoice, this mid-calf shaft leopard boot is stylish and practical. Low pile true calf hair makes a seasonal statement. Front and back pull tabs make for easy on and off. Consider half sizing up.  

Shown in Leopard Calf | $1,495 On sale, $747 at mytheresa.com

Ganni

Recycled Rubber Chelsea Rain Boot

A lighter waterproof boot for the damp, warmer locales and days that deliver plenty of sunshine to your vibe. Made of 50% recycled scraps this style is a crown pleaser style from Ganni is a go-to mudroom style.

Shown in Spectra Yellow (more colors) | $245 On sale, $147 at nordstrom.com

Blondo

HALLIE BOOTIE

An everyday boot. Beautiful neutral suede acts as a replacement to a standard black boot for the season. Style under jeans and cropped pants with your favorite chunky sweater. Features a ribbed, stretch topline, and back pull tab. Consider half sizing up. 

Shown in Dark Taupe Suede (more colors) | $150 at nordstrom.com

Dr. Martens

2976 Chelsea Boot 

Pull on your chunky marled crew socks and let them peak out of the top of these urban-cool classics from Dr. Marten. For a layering bottom style, this utilitarian style can be worn all day for all weather. Take your standard size. 

Shown in Black | $149.99 at dsw.com

Jimmy Choo

Clayton Suede Lug Sole Ankle Boots 

A workwear staple gets a luxury touch in these Jimmy Choo boots. Elastic gore shafts and back pull tabs make this supple Italian suede style a comfortable choice. Consider half sizing up. 

Shown in Brown | $895 at intermix.com

Aquatalia

DELLA BOOTS

Reliable in all the weather conditions, this two-tone green style from Aquatalia features translucent rubber soles and is constructed of Italian leather. Literally, all weather proofed and has an inside zipper in case you care not to tug too much on your boots. Consider half sizing up. 

Shown in Anthracite Green | $550 On sale, $385 at aquatalia.com

Christian Louboutin

Marchacroche Leather Ankle Boots

Classic, modern, and tasteful. This quintessential black boot from Christian Louboutin takes you from the start to the finish of your winter days. Casual yet elevated all at once, designed in Italian leather with a stretch gore shaft and extra-large back pull tabs that are sure to reduce friction on and off. Consider half sizing up. 

Shown in Black | $995 at mytheresa.com

AGL

Maxine Chelsea Boot 

For an off-duty durable weather slip-on, this polished leather boot offers a chunky tred for all your weekend errands or to and from fitness classes in the slush. The lower ankle shaft and stretch gore come together with a back pull tab. Take your normal size. 

Shown in Fossil (more colors) | $395 at zappos.com

Stella McCartney

Trace Chelsea Boot

Sustainably constructed with Vibram® soles and Alter Nappa faux leather, this winter white style from Stella McCartney is a minimalist, environmentally friendly dream. Includes a branded rear pull tug. Take your normal size, if in between then size up to full size. . 

Shown in Cream/Black | $725 at nordstrom.com

Prada

Monolith Lug Sole Chelsea Boot

Stacked, ‘90s inspired footwear is back, along with all the other trends from that decade. This urban lugged sole boot from Prada is not for the fashion faint hearted. Consider half or full sizing up.  

Shown in Black | $1,150 at nordstrom.com

Proenza Schouler

Leather Chelsea Boots 

A neutral staple style to wear every day, in a deluxe suede. Pair with chunky socks peeking out of the top or with a maxi skirt and sweater for a warmer, richer color tone. Take your standard size. 

Shown in Cream (more colors) | $825 at netaporter.com

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