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Chelsea boots have been a staple in the fashion world ever since their invention in 1851 by J. Sparkes-Hall. Originally made for men (worn by everyone from the Beatles to Kanye West), they have since become an iconic cold-weather style for women thanks to their comfort, convenience, and versatile design.
These unique boots are usually ankle-length, have lower heels, are made of rubber or leather, and have an elastic band that makes them a breeze to put on and take off. They can come in any variety of colors, from the traditional black to white to bright red.
Chelsea boots are an ideal fall and winter staple because of their combination of comfort and style. Knowing how to wear Chelsea boots can transform an easy, low-effort outfit into something that looks put-together. Because of their convenience, Chelsea boots are a favorite casual shoe style for celebs. Stars like Selena Gomez, Kendall Jenner, and even Gigi Hadid have been seen sporting a pair of Chelsea boots.
Don’t know how to wear Chelsea boots? We’ve got you covered. We’ve answered the million-dollar “how to wear Chelsea boots” question with some top-notch “steal-her-style” inspiration from trendy celebrities.
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Gigi Hadid showed us how to wear Chelsea boots by keeping her outfit simple but sleek with a black bodycon dress. It made for a trendy and comfortable, yet put-together outfit. Gigi styles her hair in relaxed waves and no accessories and absolutely pulls it off.
Mock Neck Ribbed Midi Dress, $39, Nordstrom
Yale Chelsea Boot, $90, Nordstrom Rack
Follow Gigi’s lead for how to wear Chelsea boots with a mock-neck ribbed dress and reflective vinyl-textured Chelsea boots. This is an uber-versatile look that can be worn to any party, the club, or to dinner. The midi hemline of the dress gives it a trendy-sophisticated touch that separates it from your average little black dress, and the shiny Chelsea boots are a fun twist on the original.
Street style star and model Emily Ratajkowski was was spotted wearing a red floral print midi dress with a moderate slit and heeld Chelsea boots that featured silver buckles. Her ensemble looked comfortable, feminine and edgy which makes it a perfect example of how to wear Chelsea boots.
Wallflower Dress , $248, Reformation
Auras Chelsea Boot, $125, Nordstrom
Get Emrata's simple yet chic look by teaming a floral print midi dress from Reformation with a pair of western Chelsea boots.
Olivia Culpo is ever the style queen and her Chelsea boots outfit was styled in the trendy way we've come to expect. According to Olivia's style choice, the best way to wear Chelsea boots is with a casual-sporty color-blocked mini dress. Olivia teamed a pair of crisp-white Chelsea boots with a navy blue and red form-fitting mini dress. The entire look made for an understated-chic ensemble, one that you can easily feel inspired by.
Striped Knit Mini Dress, $25, Urban Outfitters
Kensington Chelsea Boot, $160, Nordstrom
Get Olivia's look by pairing a sporty form-fitting casual mini dress from Tommy Hilfiger with these white Kensington Chelsea boots from Nordstrom.
Spotted at a DKNY fashion show, Bella Hadid wore an especially charming all-black-everything outfit that makes for great inspiration for how to wear Chelsea boots. Bella teamed a black button-down flowing mini dress with a fur vest and matte Chelsea boots. She introduced a black belt to the look to cinch her waist; the gold buckle added a vintage feel to her outfit.
Puffed Sleeves Dress, $80, Mango
Black Faux Fur Gilet, $85, Topshop
Denver Chelsea Boots, $395, Shopbop
Topshop Textured Logo Belt, $40, Nordstrom
Get Bella's look by teaming the puff sleeve mini dress from Mango, with a black fur vest from Topshop, Denver Chelsea boots, and a black belt with a gold buckle.
Olivia Palermo never passes up a good style moment. Seen here wearing a classic ensemble while carrying Topshop shopping bags, she's literally giving us fashion inception. We could spend all day theorizing the really good style work she planned to do with her new pieces from Topshop, but her Chelsea boots outfit deserves our immediate attention.
Olivia's vote for how to wear Chelsea boots is to style the shoes in a contrasting role. Olivia teamed a cream canvas that consisted of a knitted sweater, lace long-sleeve shirt, and cream midi skirt with an ultra-thin black belt and edgy patent leather Chelsea boots. The entire look is refined and chic with a surprise twist at the ankle.
Cable Knit Sweater, $50, Mango
Stelen A-Line Skirt, $62, Need Supply
Black Skinny Belt, $20, Topshop
Dr Martens Kensington Chelsea Boots, $142, ASOS
Get the look with a cream knitted sweat from Mango, a-line skirt from Need Supply, thin belt from Topshop and shiny Dr. Martens Chelsea boots.
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Seen here, Selena Gomez rocks a colorful outfit featuring a red halter bodysuit, distressed light-wash jeans, and she definitely knows how to wear Chelsea boots. It’s the perfect combination of bright summer colors and cool-weather styles. In this fit, Selena can sign autographs for fans in comfort and style.
Alona Ribbed Halter Top, $32, Revolve
Bleach Super Ripped Hayden Jeans, $90, Topshop
Suede Chelsea boots, $530, Moda Operandi
Body Bumpin Sunglasses, $35, Shopbop
Get a similar look with this bodysuit from Revolve, with the same halter neck and bright red color as Selena’s. It also has a similar revealingly open back. To imitate Selena’s ripped jeans, we recommend a pair of extra-distressed, light-wash boyfriend jeans. Lastly, the star of her outfit is her bright mustard yellow Chelsea boots. They have medium-height heels and are constructed from suede fabric and are a perfect example of how to wear Chelsea boots.
Kourtney Kardashian's Chelsea boots outfit falls somewhere in between California cool-girl and boho-chic cowgirl. Either way, this look is really good. Kourtney's take on how to wear Chelsea boots is a monochromatic ensemble teamed with a black Portofino shirt and black distressed skinny jeans. She finished the look with a black bandana necktie.
Washed Black Willow Rip Mom Jeans, $75, Topshop
Sabrina Chelsea Bootie, $398, Shopbop
Hang Chain Western Belt, $34, Urban Outfitters
Slim Fit Convertible Sleeve Portofino Shirt, $50, Express
Style a similar outfit with your favorite pair of distressed black mom jeans and a business casual blouse.
Duchess of Cambridge Kate Middleton always finds the perfect balance between posh and chic. In this picture, she’s wearing a tight-black turtleneck and black jeans paired with a tweed blazer and demonstrates how to wear Chelsea boots with a pair of black suede Chelsea boots. She looks young yet regal and is casually dressed yet follows the royal dress code. This outfit is perfect for women of all ages and is a chic way to bring a fresh look into the workplace.
Double-Breasted Plaid Blazer, $139, Banana Republic
Delafine Cashmere Turtleneck, $325, Shopbop
The Curvy Authentic Stretch High-Rise Skinny Jean, $68, Everlane
Jennica Bootie, $70, DSW
For this outfit, we’ve selected a structured plaid blazer from Banana Republic with a similar plaid pattern to Kate Middleton’s. You’ll probably already have a black turtleneck and jeans in your closet, but if you don’t, go for this cashmere turtleneck from Shopbop and sustainable black jeans from Everlane. Lastly, for the Chelsea boots, grab this affordable suede pair from DSW.
Model Kendall Jenner was captured on-the-go in the most rocker-chic look for any Chelsea boot's outfit. For Jenner, one of the best ways to wear Chelsea boots is to go full-blown glam. Kendall teamed a fur coat with a plunging neckline satin shirt, metallic black jeans, and western Chelsea boots.
Topshop Boxy Faux Fur Coat, $190, Nordstrom
Stelen Charli Lace Trim Camisole, $41, Need Supply
Good Legs High Waist Skinny Jeans, $179, Nordstrom
Valtina Chelsea Boot, $198, Nordstrom
Create a similar feel with your outfit by combining a bohemian-inspired faux fur coat, delicate satin camisole, metallic black skinny jeans, and unique Chelsea boots.
Model Cara Delevingne is a go-to inspiration for minimal-chic outfits but this time, she opted for a more grunge-inspired style aesthetic. Cara's vote for how to wear Chelsea boots is a very "DGAF" camo jacket, long-sleeve flannel, and beanie outfit.
Ruthie Camo Jacket, $60, Urban Outfitters
Urban Renewal Oversized Flannel Shirt, $39, Urban Outfitters
Western Chelsea Boots, $87, ASOS
Fawcett Jean, $128, Reformation
Nail this free-spirited aesthetic by teaming a camo jacket and red flannel shirt from Urban Outfitters, western Chelsea boots from ASOS and raw hem jeans from Reformation.