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Article: How to Wear Chelsea Boots

How to Wear Chelsea Boots - EOS Footwear

How to Wear Chelsea Boots

 A classic Chelsea boot is the denim of the shoe world – endlessly wearable, effortless, and versatile. Reimagined time and again, this enduring silhouette often becomes a favourite wardrobe staple, once you figure out how to style it. 

Here, we take a look at how this iconic boot came to be, along with some styling suggestions from the Chelsea connoisseurs. 


EOS Chelsea Boots Freya


What are Chelsea Boots? 

Chelsea boots have been simplifying street-ready style since the Victorian era. Queen Victoria’s very own cobbler lays claim to the first slide-on design in the mid-1800s, at a time when horses were the main method of transportation. Known then as ‘paddock boots’, the elasticated sides offered more flexibility, perfect for riding. Characterized by their close fit and iconic elastic inserts, Chelsea boots often also feature a loop pull tab to the rear to help you quickly slip them on and off. 


EOS Chelsea Boots Robyn
By the middle of the 20th century, Chelsea boots earned their modern name when they graced the feet and streets of London’s art and socialite scene. From then on, every famous face from The Beatles to The Rolling Stones was seen wearing a pair. They quickly gained international acclaim, favoured by men and women alike for their endless adaptability. In turn, this led to a cacophony of countless variations, from the addition of a Cuban heel to chiselled, pointed toe profiles. 


An age-old question spanning two centuries, you might wonder; ‘are Chelsea boots formal, or casual?’ Well, with just a little wardrobe consideration, they can be both. High-quality craftsmanship is what ensures your boots stand the test of time, with a silhouette that never succumbs to fleeting styles or trends. 

How to Style Chelsea Boots…

For a Causal Look  

A pair of classic Chelsea boots with your favourite denim jeans is the epitome of carefree street style. Jeans can be tucked in or out depending on the style that suits you best. Skinny or slim-fitting styles should be cropped to the top of your boot for a clean, streamlined look. Try something with a tapered fit around your ankle, such as Celina

If you prefer the look and comfort of looser denim, try a boot with a lower cut on the ankle, as showcased by Serenity and Wild. Longer jeans can drop casually down over the boot, or be rolled at the hem to align. This draws attention to your ankle, which elongates your legs by accentuating their slimmest point. Finish the look with a turtle neck top or your favourite tee, and an oversized blazer or coat. 

For a Fashion-Forward Ensemble 

There’s something wonderfully unintentional about a Chelsea boot when paired with a skirt or dress. One for the style-conscious, this look is carefully considered without appearing so, the same way you might ‘throw on’ a jumper over a silk slip dress. The key here is in the heel. 


EOS Winter 22 campaign

When pairing ankle boots with skirts, a little lift can prevent your legs from looking ‘cropped’ and appearing shorter than they are. A flowing midi skirt can enhance the elongation effect; opt for something pleated for added ‘it-girl’ points. Try comfortable Casey for everyday errands, or heeled Castel for elevated occasions. 


EOS Chelsea Boots Casey


If you choose a shorter or slimmer fitting skirt, pay attention to colours. Opt for lighter shades that tone in with your skin to avoid drawing the eye downwards or pair with dark stockings for a more seamless look. Westero adds an unexpected twist to the classic profile, with an elegant Cuban heel and sleek pointed toe. Pair it with a button-down skirt and blouse for a soft yet sophisticated look. 

For Classic Androgenous Appeal 


EOS Chelsea Boots Corby


To embrace the gender-neutral versatility of Chelsea boots, trousers are the way to go. Update the look with a modern Chelsea iteration that adopts utility elements. Feat brings beautiful, bold attitude with an oversized sole and deep lugs. Make a style statement by pairing them with tailored separates. Alternatively, add leather-look trousers and keep colours monochrome on top. A cropped jacket or blazer can add an edge of femininity here.

For a softer look, Freya features a textured rubber sole that looks fantastic with cropped boyfriend jeans or boot-cut trousers. Finish the casual, country chic look by tucking in a checked shirt.


EOS Chelsea Boots Freya


A Wear-With-Anything Wonder 

If you struggle to style different outfits, your solution is to choose a Chelsea boot that works harder for your wardrobe. Willo is one of those signature styles, with an eternally popular profile that fits perfectly alongside skirts, jeans, and dresses. Expertly finished in Portugal, it features sumptuous gathered leather that is both slouchy and sophisticated.


EOS Chelsea Boots Willo
Discover Willo

Shop the Chelsea Collection 

Our collection embraces the wildly comfortable, carefree nature of the design with a range of added elements to complete any composed or casual look. From low flats to help you stay light on your feet to smart heels for a little added lift, you’ll also find styles with a distinct nod to other iconic boot categories. Whether you want to take a walk on the Wild West side or embrace combat chic, we have a beautifully made Chelsea boot for you.


EOS Chelsea Boots Feat


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