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The Best Women’s Chelsea Boots The Best Women’s Chelsea Boots

The Best Women’s Chelsea Boots

The History of Chelsea Boots & Buying Guide

If you’re looking for women’s boots that toe the line between effortless and sophisticated, Chelsea boots are among the most versatile styles in the world, thanks to the distinctive elastic goring at the side. Snuggly hugging your ankles, these stretchy panels make laces unnecessary and make women’s Chelsea boots a particularly comfortable style.


The origin of the Chelsea boot is steeped in history, taking us back to 19th-century England to where they were created with one particularly important woman in mind. It was Queen Victoria’s royal bootmaker, J. Sparkes-Hall, who is credited with first applying elastic panels to footwear as an alternative to buttons or laces. The Queen herself was said to have requested a boot that was easier to slip on and offer for riding and proved to be an avid fan of her bootmaker’s new design. These new “elastic ankle boots” became a relatively popular style for women (and later men) for their highly functional purpose.

It wasn’t until the 1960’s that Chelsea boots earned their modern name. As this style came back into fashion, the mod set around the West London neighborhood of the same name adopted it as part of their unofficial uniform. Second only to go-go boots in the popular memory of “Swinging London,” Chelsea boots could be seen worn by models like Jean Shrimpton or Twiggy to rock stars like the Beatles. Combining high function with high fashion, Chelsea boots reached the masses and the name has stuck ever since.

Design Details

While a Chelsea boot looks simple in appearance, that very simplicity means that the details are critical to make a high-quality product. Relative to other styles, you need a large, single piece of leather for the vamp, which means any compromise in your cutting criteria will result in imperfections in the boot. Shaping the vamp also requires talent, since the leather needs to be “tamed” to make it curve correctly to meet the shape of the wearer’s instep. Overlooked details separate true quality from the rest.

Different designs impact the shape of the elastic cutout, which is mostly an aesthetic choice, but the materials used in the upper and outsole can completely transform the look of a pair of Chelseas. For year-round use, a rubber outsole fends off rain and provides better shock absorption for long walks. Full grain leathers produce a more formal look, while oiled suede brings a coziness to the boot perfect for more informal settings. Waxed suede blends the functional and the fashionable, naturally burnishing as the boots are worn to create a distressed look that improves with wear.

How to Style Women’s Chelsea Boots

If you want some effortless style, a pair of Chelsea boots made in a beautiful full-grain leather like the Old English Duchess adds immediate polish with your favorite pair of denim.

How to Style Women’s Chelsea Boots

When you’re looking to wow, a higher heeled Chelsea boot like the Black Avenue Boot is equally fun and flirty with a dress as it is with black leggings.

Our Favorite Women’s Chelsea Boots

The Best Everyday Chelsea Boot: The Dark Olive Suede Duchess

Key Features: Dark Olive WeatherSafe™ Suede, Poron® Antimicrobial Shock Absorbing Insole, Flexible Elastic Goring

Why we love it: The Dark Olive Suede upper goes with almost everything in your closet and seamlessly blends form and function to create one of the most comfortable boots in our collection. Easy to dress up or dress down, the Duchess does not disappoint.

What others say: “They are extremely comfortable… I also really like the olive color…kind of understated, it goes with almost everything.” - Dawn L.

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The Best Classic Women's Chelsea Boot: The Black Duchess

Key Features: Black Full-Grain Leather, Full Glove Leather Interior Lining, Poron® Antimicrobial Shock Absorbing Insole

Why we love it: There’s something about a beautiful black leather boot makes you feel calm, cool, and collected. The understated detailing and cushy insole complete the trifecta to make this boot formal enough for the office but comfortable enough for all-day wear.

What others say: “Fall’s Best Boots for Under $200.” - Vogue

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Wrapping Up

Chelsea boots are staples and it’s not hard to see why. Their unique design, high comfort, and extreme versatility make them an excellent complement to almost anyone’s wardrobe. For whatever long and winding roads you may encounter, there’s nothing quite like a pair of Chelsea boots to help you on your journey.

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