How To Wear Chelsea Boots [Style Guide]

A quality pair of Chelsea Boots is a wardrobe staple all year round, which is why we want to make sure you know how to make the best out of them this season. Reliable, durable and timelessly fashionable, the Chelsea boot has elegantly withstood generations of fashion movements and continues to be a popular footwear choice for a range of occasions.

Sometimes made from supple leathers, soft suedes, snakeskin and more, as well as durable elastic the Chelsea boot is available both heeled and flat and will accentuate a range of clothing styles and dress preferences.

 The Chelsea boot is a versatile piece of footwear that we want to be sure that you’re taking full advantage of.

How To Wear Chelsea Boots With Different Clothing

Despite being an ankle boot, Chelsea boots aren’t constricted to winter-time use. Paired with the right clothing, Chelsea boots will meander with you from season to season to provide you with a comfortable sole all year round. You just need to know what to pair them with.

How To Wear Chelsea Boots With Jeans

Matching jeans with Chelsea boots is a classic, no-fail style combination for every and any event. Whether it’s a heeled Chelsea boot or a flat one, pairing your boots with mom jeans or skinny jeans will create an effortless look that will look good anywhere.

For an everyday look, pair your jeans and Chelsea boots with a basic, white t-shirt and go for the ultimate laid-back, comfort that will never go out of style. 

To dress them up a bit in the winter think a long trench-style coat with a bold, statement scarf. Why not choose brightly coloured or patterned Chelsea boots to make your outfit pop and to show of your jeans and boots look in the most stylish way. 

Perfect from Autumn to winter, this classic Chelsea boots look is timeless year after year and will be an easy throw-on outfit all throughout winter.

How To Wear Chelsea Boots With Dresses

Pairing Chelsea boots with a dress is a fashion choice that works; it’s comfortable, looks good and will create the perfect balance of casual and formal for all the right occasions. Skater dresses, shift dresses, fitted or woollen – all styles of dresses can be paired easily with the Chelsea boot for an elegant look with maximum comfort.

In the summer, matching a dress with Chelsea boots is the perfect go-to outfit, and a pair of black or brown Chelsea boots will soon become a staple part of your summer wardrobe.

In winter, Chelsea boots, woolly tights and a long sleeve midi dress can create the perfect look. Dressed to face the cold and looking good whilst you do it, Chelsea boots are an all-season must-have to pair with dresses.

How To Wear Chelsea Boots With Leggings

Leggings are no longer only for the comfort of your home, the stretch fabric of leggings has made its way into the public eye, making them the perfect pairing for Chelsea boots. 

Wearing Chelsea boots with leggings will become a winter fashion staple for you the moment you try it; paired with chunky knits and warm scarves, they’re an unbeatable combination for maximum comfort and winter style. 

How To Style Heeled Chelsea Boots

You can style your heeled Chelsea boots exactly like your flat ones. Designed similarly but with added height, the heeled Chelsea boot will help formalise your outfit and prepare you for any event. 

Are Chelsea Boots Suitable For Winter?

As the ultimate ankle boot, the Chelsea boot is very suitable as a winter boot. Made from durable leather and strong elastic a good pair of Chelsea boots is the perfect choice to keep your feet warm and dry this winter.

Take care protecting your leather Chelsea boots for the winter; clean them regularly, condition the leather and make sure to waterproof them. This will make sure they’re covered for you to step out in style, whatever the winter weather. 

For full advice on how to winter-proof your boots take a look at our Winter Boot Care Guide. 

Are Chelsea Boots Unisex?

Yes! The Chelsea boot style is unisex and can complete a range of fashionable outfits for both men and women. The subtle, no-fuss style of the Chelsea boot means you can co-ordinate them with a work suit, pant-suit, dress, jeans and more to create a fashionable style and keep your feet well protected from the cold, regardless of your gender.

A good pair of Chelsea boots should make the important foundations of anybody and everybody’s shoe cupboard, made from luxurious materials that are crafted to keep the feet snug and warm. Everyone will benefit from having a pair of Chelsea boots in their wardrobe.

How Should Chelsea Boots Fit? 

Chelsea boots are perfect for all; the elastic fabric means that they’re an ideal ankle boot for wide feet to slip into without a hitch, whilst the leather still provides a solid fit once your foot is in the boot for a well-supported walk. Use the handy little hoop at the back of your Chelsea boot to pull it onto your foot and away you walk.

Chelsea boots shouldn’t be oversized and mainly run true to size, usually without an issue. If the elastic makes them a little loose around your ankles, then a thicker pair of socks usually fixes this problem. 

Overall, the Chelsea boot is a unisex, all-season, every-occasion boot that is a must-have for everyone. Often available in a range of styles and designs, the Chelsea boot is an evergreen staple of fashion that will provide soft, plush comfort to your soles when made from the right materials. Complimentary for workwear, formal wear, casual clothes and party dresses, opting for a Gabor Chelsea boot is always a good option.