Timberland IE Home
Cart

How to style men’s Chelsea boots

2024-05-13

How to style men’s Chelsea boots

Thinking of purchasing a pair of Chelsea boots, but unsure what to wear with them? We’ve broken down exactly how to style these versatile, on-trend boots, from what jeans to wear to what colours to avoid. But before we go into how to style them, it’s important to know exactly what Chelsea boots are and how they’re different from chukka boots or our original 6-inch boots.

What are Chelsea boots?

Chelsea boots are close-fitting, ankle height boots, that don’t require any laces or buckles – thanks to their elasticated panels either side of the ankle. The boots were first made by J. Sparkes-Hall, cobbler to none other than Queen Victoria, and for over 150 years they have been worn by some of the most fashionable men and women.

At the time they were known as ‘Paddock boots’, and were mainly used for country walks and horse riding. It wasn’t until the 1950s and swinging sixties that the boots were given their current name, thanks to their popularity amongst the fashionable ‘Chelsea set’ in London. During this time a Cuban heel was adopted in the design, and the boots were soon seen on everyone, including The Beatles. The design has continued in popularity to this day and is still a fashionable and versatile wardrobe staple.

Cool and classic: Wear Chelsea boots with jeans

One of the easiest ways to wear Chelsea boots is with a pair of classic slim fit jeans. Cool and casual, this classic denim and boots combination can carry you from day to night in an effortless and stylish way.

To match the right boots to jeans, it’s important to know which denim washes will work with different colour boots. The simplest and perhaps most stylish combination is black Chelsea boots with a pair of black slim-fit jeans. Understated and sophisticated, the all-black pairing will work for everyone.

However, if you opt for a pair of brown Chelsea boots, it’s best to pick a pair of blue jeans. But it’s always worth bearing the denim wash in mind. If you have a pair of dark brown boots, like our Larchmont Chelsea Boot in dark brown try pairing them with a lighter blue denim, like our Sargent Lake Stretch Jeans in blue.

Similarly, if you have a lighter boot, like our Elmhurst Chelsea boot in brown, try pairing them with darker denim, like our tapered Tacoma Lake jeans in indigo.

Stylish and sophisticated: Wear Chelsea boots with a suit

Formal dressing can sometimes be a bit of a nightmare – figuring out which suit goes with what shoes can give even the snappiest of dressers a headache, but one of the sophisticated ways you can wear Chelsea boots is with a suit.

Whether it’s a day in the office or an occasion like a winter wedding, pairing your Chelsea boots with a more formal outfit will give the overall look a bit of an edge. As with jeans, colour matching is important here, so the rule of thumb would be: blue suit and brown Chelsea boots, black suits and black Chelsea boots.

Chelsea boots are an essential part of your winter wardrobe

Aside from being great with jeans and suits. Chelsea boots should be a part of your regular winter wardrobe. All of our Chelsea boots are made to cope with all weathers, and will keep your feet warm and dry throughout winter, so why not pair them with your favourite Parka or Field jacket, and wrap up in your hat and scarf, for an all weathers look that’s bound to impress.

How to take care of your Chelsea boots

No matter how you wear your Chelsea boots it’s important that you also take care of them. All our Chelsea boots are made from premium full-grain leather or waterproof suede, and can last for years when taken care of properly. It’s worth investing in a good quality leather cleaner like our Boot Sauce, or a boot care kit for a more comprehensive set of products to help keep your boots in top condition for years to come.

Whether you wear them with jeans, a suit, or adopt them as a part of your winter wardrobe, it’s clear that Chelsea boots have come a long way from paddocks of 150 years ago. They’re some of the most versatile boots you can own – making them the perfect choice for those who want to get the most out of their footwear. Wearable, stylish and durable, whichever pair you choose from our range, and whichever way you decide to wear them, there’s no doubt that with the right care, they’ll last you for years to come.