How to Wear Chelsea Boots, According to a Stylist

Alexandra Imgruth weighs in on the fall fashion favorite.

 Xiayan Guo wearing a red short dress with floral design and white mesh and white leather Chelsea boots outside Stella McCartney during Paris Fashion Week on March 07, 2022 in Paris, France.
(Image credit: Getty/Jeremy Moeller)

Chelsea boots, one of fashion's most beloved staples, hearken back to Queen Victoria—for whom the very first pair was made in 1837. Since then, the style, differentiated by an elastic side panel, has become one of the most popular types of boots (opens in new tab) for fall weather in England and worldwide. While ankle boots (opens in new tab) and thigh-high boots have grabbed the spotlight lately, celebrity stylist and costume designer Alexandra Imgruth says Chelsea boots should be a fall (wardrobe) staple to add to your boots rotation. 

If you're left wondering how to style Chelsea boots, we've tapped Imgruth to share her professional tips on how and what to pair with an array of Chelsea boot styles. Read on for valuable, vintage-inspired fashion inspiration that will have you counting the days until autumn.

Pair Your Chelsea Boot With Skirts and Tights

Selena Gomez is seen on set for "Only Murders in the Building" in the Upper West Side on March 30, 2021 in New York City.

(Image credit: Gotham/GC Images)

I love wearing short skirts with tights to the office or on a night out with friends, and Imgruth agrees. "I mainly wear my Chelsea boots with sheer black tights and a mini skirt or mini dress," she says. "Pairing the boots with a skirt or dress makes them easy to transition from day to night, and the short length gives a mod, 60's feeling." For that fun, English mod vibe, check out some of our top picks below.

Style Your Chelsea Boot With Mini Dresses and Tights

Maria Wos wearing black dress with embroidery and blue bag and Petra Henriette Rufi wearing long white dress, black vest with embroidery, grey coat, grey bucket hat and Ganni bag outside A. Roege Hove in Copenhagen fashion week Autumn/Winter 2022 on February 02, 2022 in Copenhagen, Denmark.

(Image credit: Raimonda Kulikauskiene/Getty Images)

As mentioned, the short skirt/dress-and-tights look pairs fabulously with Chelsea boots, and a dress is a nod back to the boots' English roots." A mini dress is at the core of the iconic 1960s London mod style," says Imgruth. Add a print or pattern to complete the look.

Style Your Chelsea Boot With Jeans

Influencer Nadine Tosun wearing a blue patchwork denim jeans jacket by Topshop, blue denim jeans pants by Isabel Marant, a grey pullover by Edited, a grey Balaclava by Nadine Tosun the Label, grey boots by Copenhagen Studios, a grey bag by Balenciaga ans sunglasses by The Attico during a street style shooting on January 27, 2022 in Munich, Germany.

(Image credit: Getty/Streetstyleshooters)

I love a good pair of jeans for their ability to match almost anything, so donning denim is the perfect opportunity to experiment with Chelsea boot materials and styles. While she prefers a classic leather Chelsea boot, Imgruth says that a beautiful suede can work too, and she suggests an animal print if you're more experimental. Ahead, check out some suede options from Imgruth's go-to Chelsea boot brand, Crockett and Jones.

Style Your Chelsea Boot With a Suit

Nathalie Larche wearing full black and white Dior look during Paris Fashion Week on January 20, 2022 in Paris, France.

(Image credit: Getty/Jeremy Moeller)

Who says your fashion inspiration needs to be limited by gender? Imgruth says that Chelsea boots are an excellent pairing for a suit if you're feeling a little more formal. Take a note from one of the most famous bands of all time and pair your favorite Chelsea boots with a sleek, head-turning suit. "Think of The Beatles crossing Abbey Road," Imgruth says.