How to style Chelsea boots

How to Style Chelsea Boots

So, you’re looking at a pair of Chelsea boots. But how will you style them? What will you wear with them? Luckily, Chelsea boots are popular for their versatility. Forget buying multiple pairs of shoes for different outfits. You can dress your Timberland® Chelsea boots up or down for almost any occasion!


What can I wear with Chelsea boots?

The timeless shape and design of Chelsea boots make them a sophisticated fashion icon for both casual and formal looks.

Chelsea boots are a classic wardrobe staple that can be paired with almost any outfit, whether it’s workwear, formal wear or casual wear. Guys often wear Chelsea boots with suits, chinos or jeans, while women can pair them with dresses, skirts or pants.


How do men wear Chelsea boots?

Men can wear Chelsea boots to achieve either casual or formal looks. They can add to a dressed-down, laid-back vibe with jeans, a t-shirt and a casual jacket – or you can wear them with suits and blazers for special occasions and business meetings.

Wearing a suit? Let your Chelsea boots fall neatly over the top of your trousers for a suave, unfussy look – don’t tuck them in!


Can I wear Chelsea boots with a suit?

Chelsea boots are a classic footwear option when it comes to suits. Men have been pulling off the suit-and-Chelsea-boot look for decades. Both stylish and comfortable, leather Chelsea boots are effortlessly versatile and can also be paired with casual outfits as well as suits.

Wearing a suit with Timberland Chelsea boots? Ensure your trouser hem is short enough to show them off. Pair black Chelsea boots with black suits and brown Chelsea boots with navy suits.


Can you wear Chelsea boots in the summer?

Chelsea boots are suitable for rain or shine, and year-round wear, depending on what you wear with them.  Men often team their Chelsea boots with jeans and t-shirts for a casual summer vibe, while women team Chelsea boots with skirts and dresses for a vintage look.

When the sun’s out, wear your Timberland Chelsea boots in the full confidence that you’ll not only look effortlessly stylish but feel supremely comfortable too. And even when it rains, we usually have waterproof Chelsea boots in stock.  Take a look at our men’s and women’s Chelsea boots for all occasions and seasons.


What is the best color for Chelsea boots?

The best color Chelsea boots depend on the look that you’re aiming for and what YOU like! While black boots are ideal for dark outfits, lighter-tone clothing usually goes better with brown boots. 

Timberland usually has a good variety of neutral-colored boots that go well with pretty much any ensemble you put together.


What can I wear with black Chelsea boots?

Whether you’re opting for a formal or casual look, there are plenty of ways to wear black Chelsea boots. Pair with slim- or skinny-fit jeans and a navy overcoat for a stylish look. Alternatively, plain t-shirts and jumpers look both casual and fashionable when paired with black Chelsea boots. Finish the look with a double-breasted coat or biker jacket.

Take a look at your wardrobe to decide which color Chelsea boots would best suit your outfits. You can wear your Chelsea boots with virtually any clothing, so many people just pick a color that they can make the most of and wear year-round.