How to Style Chelsea Boots, According to a Stylist

Publish date: 0001-01-01

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 for fall weather in England and worldwide. While ankle boots 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 Chelsea boots outfits for autumn and beyond.

Style Your Chelsea Boots With Skirts and Tights

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.

Madewell Buckle-Belt Wrap Mini Skirt in Plaid

Missoni Sequined Crochet-Knit Mini Skirt

Calzedonia 20 Denier Ultra Comfort Sheer Tights

Sheertex Sheer Rip-Resist Tights

Thursday Boots Knockout

Thursday Boots Dreamer Bootie

Style Your Chelsea Boots With Mini Dresses and Tights

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.

Free People Mira Mini

English Factory Mixed Media Mini Dress

Wolford Tummy Control Top 20 Denier Tights

Spanx Luxe Leg High-Rise 60 Denier Shaping Tights

Blondo USA Hallie Waterproof Bootie

Softwalk Indy Chelsea Boot

Style Your Chelsea Boots With Jeans

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 Imgruth prefers a classic leather Chelsea boot, she 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.

Sézane Abélia Blouse in Ecru

Lilysilk The Amalfi Stripe Silk Shirt

Miaou Lou Pants in Cow

Made In Tomboy Jey Rigid High-Rise Wide-Leg Jeans

Crockett and Jones Bonnie

Ganni Topstitched Leather Chelsea Boots

Style Your Chelsea Boots With a Suit

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.

Theory Carissa Blazer in Good Wool

Kate Spade Jewel Button Velvet Blazer

Theory Demitria Pant in Good Wool

Kate Spade Velvet Pants

Sam Edelman Laguna Chelsea Boot

Banana Republica Hudson Tall Leather Chelsea Boot

Meet the Expert

Alexandra ImgruthStylist

Alexandra Imgruth is a fashion stylist and style consultant who works with celebrities and priavte clients alike. She is currently based in New York City.