How to Wear Chelsea Boots for Women

A Bit of History

Originally known as the paddock boot, the Chelsea boot has had a long and dynamic history. The boot was originally crafted by Queen Victoria’s shoe maker, Joseph Sparkes-Hall, who patented the boot in 1851 after it was worn by the queen. The boot gained a great deal of popularity in the Victorian era due to its versatility and comfort. One key point was the ease with which the boot could be put on and taken off, which was as a result of the two elastic panels placed on both sides of the ankle.


Chelsea Boots - Victorian Style

Moving into the 1950’s and 60’s, the boot went through a kind of re-branding. The boot gained its new name the Chelsea boot, as a result of the Chelsea set – a group of creatives and socialites that hung about the area of Chelsea, London, and wore the boot. In the 1960’s a cuban heel was added and this addition plunged the boot into stardom as it began to be seen on the feet of famous wearers. Celebrities such as members of The Rolling Stones, The Beatles and Jean Shirmpton were regular wearers of the Chelsea boot.


Chelsea Boots- The Beatles

The Beatles x Chelsea Boots.


Trousers and Chelsea Boots

The addition of higher and varying heel shapes to the Chelsea boot has made the boot more versatile, particularly for women. Chunky heels, cool prints and contrasting rubber panels have given women more creative styling options. One of the most common ways to style this boot is with straight or skinny leg trousers, to really show it off, especially if the boot has a unique print or colour.

Chelsea Boots - Alexa Chung

Out running errands in New York’s East Village in early 2017, Alexa Chung styled a pair of R.M Williams Chelsea Cuban heel boots with dark washed skinny jeans, a navy jumper and an oversized cheetah print fur coat. She kept her cool girl chic by accessorising the outfit with a pair of cat eye Gucci sunglasses.

Chelsea Boots - Kendall Jenner

Kendal Jenner also reached for the Chelsea boot and skinny trousers style while out and about in New York in 2015. The Kardashian-Jenner sister sported a pair of Alexander Wang Anouck Chelsea boots with a pair of skinny leather trousers while taking a break from her many runway appearances.

Here some Chelsea boots available on our Shop.


Chelsea boots women


Chelsea Boots - Victoria Beckham

Even former spice girl and fashion designer Victoria Beckham wears Chelsea boots. Notorious for only wearing heels, the mother of four was spotted in flat Chelsea boots while running errands in London with her son Romeo in 2013. VB styled her black Chelsea boots with a pair of dark washed jeans, folded at the bottom to show off the boots. She wore an oversized black coat and oversized sunglasses that completed the look.


Skirts, Dresses and Chelsea Boots

Another popular way to style the boot is with skirts or flowy dresses. The contrast between the masculine boot and the girly flirty dress adds edge and sex appeal. The introduction of a higher heel to the Chelsea boot also helps to elongate the legs.

Chelsea Boots - Skirt Just Julie

Californian blogger Julie Sariñana (@sincerelyjules) shows us how to style a Chelsea boot with a midi skirt. Julie wore a black split skirt with an oversized high neck jumper. She accessorised her outfit with a wide brim hat and a black oversized tote.

Chelsea Boots - Jaime Chung

At Coachella 2013, Jaime Chung created a cool girl festival outfit by pairing Chelsea boots with a floral dress and a denim jacket.


Cool Girl x Chelsea Boots

Chelsea boots can be seen on fashionistas across the globe as their go to footwear choice.

Chelsea Boots - Karenbritchick

Blogger Karen Blanchard (@karenbritchick) of ‘WhereDidUGetThat’ created a chic street style outfit. Karen styled these gold Chelsea boots with a pair of dark skinny jeans and a camel coat. She let her gold boots stand out as the main attraction.


Chelsea Boots - Emily Ratajkowski

In 2015 Emily Ratajkowski attended the David Kordansky Gallery celebration of Jonas Woods Painting and Drawings in NY. She wore a printed wide leg jumpsuit, styled with a pair of khaki Chelsea boots.


Chelsea Boots - Bella Hadid

In April 2016 Bella Hadid rocked the sidewalks of New York in a double denim outfit. Baring her midriff, the young model wore a black crop top with an oversized denim jacket and blue ankle jeans. Her edgy street style outfit was made complete by incorporating a pair of black high heel Chelsea boots.


Chelsea Boot - Marble

Dress, skirts, trousers oh my! The styling possibilities with the Chelsea boots are absolutely boundless. Such versatile shoes, whether you are heading out with friends, to a festival, work or just running errands, your Chelsea boots will never fail you.