How to Wear Chelsea Boots in 2021 Like the Stylish Fashionista You Are

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There are few fall boot styles easier to pull off than Chelsea boots. Literally—the signature stretchy gussets on either side make it a breeze to slip into and out of this classic bootie, making them an absolute must-have—even over trendy cowboy boots or sleek knee-high styles—in our opinion. But rather than repeat the same outfits from last year, we sought out some new inspiration for how to wear Chelsea boots. Here are seven looks to try in 2021, plus a few of our favorite styles to shop ASAP.

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woman wearing black chelsea boots and a white coat
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1. sleek, Tailored Clothing + Tough Black Styles

Black leather booties or those with an exaggerated lug sole can look better suited for a muddy hike than a stroll through the city. But when paired with super-sleek tailoring—like a gorgeous wool-cashmere wrap coat in stark white, a sharp suit or even simple dark-wash, non-distressed skinny jeans and a crisp button-down—these tough Chelsea boots suddenly feel much more chic.

Shop similar styles: M.Gemi boots ($298); Ted Baker London coat ($675); Staud bag ($295)

woman wearing chelsea boots and a miniskirt
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2. mini Lengths + Ankle Booties

Show off those gams by pairing Chelsea boots that hit right at your ankle with miniskirts or dresses rather than longer hems. Just be sure to keep your heel height to two inches or lower or you might throw your proportions out of whack. And try adding a blazer over the top for an extra professional-looking touch.

Shop similar styles: MIA boots ($90); J.Crew blazer ($268); Theory dress ($315)

woman wearing tall chelsea boots
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3. casual Separates + Tall Chelsea Styles

OK, so these definitely aren’t classic Chelsea boots. But this hybrid style, which mixes in a lug sole and taller shaft height, is majorly trending right now. Balance out the military-inspired vibe by wearing these with cute casual pieces, like a kitschy patterned sweater and mini skirt or cropped flared jeans and a preppy mac jacket.

Shop similar styles: Steve Madden boots ($150); Everlane jacket ($98); ASOS Design sweater ($32); Girlfriend Collective skirt ($58)

woman wearing white chelsea boots and neutral hues
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4. mixed Up Neutrals

Rather than sticking to just one hue or a timeless all-black ensemble, try mixing as many neutral hues as you can into one look. Don’t bother trying to match your boots to your bag or your blouse to your jacket, either—just go for a full calico-coat inspired look with as many different hues as you like.

Shop similar styles: Marc Fisher Ltd. boots ($199; $150); Sam Edelman coat ($320); J.Crew turtleneck ($37); Club Monaco pants ($130); Nathan bag ($295)

woman wearing brown chelsea boots and a denim skirt
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5. denim + Brown Suede Or Leather

Brown suede booties, no matter the style, come with an inherently western vibe. But while wearing true cowboy boots with head-to-toe denim can look a bit costumey, brown Chelsea boots lend a more sophisticated air to your ensemble. This is doubly true if you opt for a black or gray wash over classic blue, or a denim dress rather than straight-leg jeans.

Shop similar styles: Børn boots ($155) Kate Spade New York dress ($278; $139)

woman wearing white chelsea boots and a plaid shirt
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6. cabincore Staples + Mod White Boots

Yes, you can always rock your stark white ‘60s booties with blue-wash jeans and a cute blouse, but this unexpected combo feels much more interesting and fashion forward. Opt for plaid shackets, cargo pants, leggings and easy tees that don’t have too much white in them to really allow your boots to pop.

Shop similar styles: Aster boots ($225); Tna shacket ($78); Reformation pants ($148); A.P.C. bag ($525)

woman wearing chelsea boots and jeans
Melodie Jeng/Getty Images

7. classic Denim + Any Chelsea Boots

When in doubt, you can never go wrong with straight leg jeans that hit right at the top of your boot. This look may not be the trendiest, but it’s guaranteed to leave you looking posh and polished every time. As for a top, we love a simple slim-fit turtleneck or cashmere knit for colder months and a slightly oversize graphic tee with a cropped jacket for spring or summer.

Shop similar styles: Treasure & Bond boots ($80); Abercrombie & Fitch coat ($220); Everlane turtleneck ($); Rolla’s jeans ($99); Louis Vuitton bag ($1,540)


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8. everlane The Italian Leather Chelsea Boot

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9. caslon Miller Water-resistant Chelsea Boots

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10. Timberland Courmayeur Valley Chelsea Boots

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11. Coach Lyden Leather Chelsea Boots

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12. Dr. Martens Leonore Sherpa-lined Chelsea Boots

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13. Ganni Low Chelsea Boots

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14. Sam Edelman Laguna Chelsea Boots

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15. Louise Et Cie Varsan Platform Chelsea Boots

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16. Nisolo Leather Chelsea Boots

stuart weitzman how to wear chelsea boots
Stuart Weitzman

Abby Hepworth


Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...
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