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

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)

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)

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)

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)

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)

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)

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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