Lookin' Good

Here’s Your Guide To Styling Chelsea Boots

Harry Styles is quaking.

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It’s no longer 2015, but the Harry Styles Chelsea Boot era is still alive in my heart, and luckily, the style is still going strong. The block heels and elastic sides have made these shoes timeless. Ahead, inspo to style these classics in ways Harry Styles could never (JK).

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You don’t have to go back to skinny jeans that can easily be tucked into your Chelsea boots. Instead, you can take your straight-leg pants and roll them up twice so people can still peep your cute kicks.

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Faux Leather Pointed Toe Chelsea Boots
Nasty Gal

The faux leather of Nasty Gal’s Chelsea Boots $27, Nasty Gal) gives them a sleek sheen. At 4 inches, this heel is taller than most, so if you like the look and feel of high heels, these are right up your alley.


Mini skirts are always a good call, especially since they’ll allow your Chelsea boots to really stand alone from the rest of your outfit. If your boots have a funky pattern, a bottom with a shorter hemline will ensure everyone notices.

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Chinese Laundry Good Day Chelsea Lug Boot

You’ll definitely want to show off Chinese Laundry’s Chelsea Lug Boot ($90, Buckle). The snakeskin is both graphic and neutral while the slight platform helps keep your feet comfortable.


If you like to keep things vibrant, you can snag a pair of solid-color Chelsea boots and use them as a base for a color-blocked look or a statement in an otherwise neutral look.

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UO Chloe Chelsea Boot
Urban Outfitters

Urban Outfitters’ Chelsea Boot ($79, Urban Outfitters) comes in a rich maroon shade with crocodile-skin details. Pair these with a mustard yellow and light blue fit, and boom! You’re a color-blocking genius.


It may be Styles’ fault, but Chelsea boots always seem incredibly posh and British to me, which is probably why I often picture them with tights. If your tights are the same color as your boots, they don’t stand out as much, but the tights add a put-together touch that will also keep you warm (and stave off blisters).

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London Rebel Platform Chelsea Boots in Black Croc

According to reviewers, London Rebel’s Platform Chelsea Boots ($26, ASOS) are comfortable, not too heavy, and high-quality. Your new everywhere shoe? I think so.


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