My Favorite Ways to Wear Chelsea Boots: The Sharpest Type of Men’s Footwear

You have plenty of options.

I’ve long been a huge fan of Chelsea boots. They’re often called Beatle boots in the U.K due to being worn by the band, but it was their association with the music scene in the 2000s that interested me. I remember buying my first pair as a student from Topman and wearing them pretty much every day with a pair of black skinny jeans and a cheap pea coat from Primark.

But, that wouldn’t make a particularly interesting article about Chelsea boot outfits. My tastes have evolved, fortunately, and I’m now happy pairing the boots with a far larger variety of styles. Although there are still undoubtedly leftovers from this time. Most notably my preference for skinny jeans. I am yet to decide if the trend for wide jeans is one I want to experiment with.

How to Wear Chelsea Boots?

When wearing my Chelsea boots I like to fold the jeans up so the cuff just touches the top of the boots. This stops them bunching up and ensures the lines of the outfit are clean. Sometimes I’ll fold them a little higher and wear a pair of colorful socks underneath.

I love wearing Chelsea boots with smart casual outfits. I think a black pair of Chelseas gives an outfit an edge that other shoes don’t provide. While you can wear them with tailoring, I tend to prefer shoes with my suits. Maybe that’s just because I don’t have enough opportunities to experiment on that level.

They definitely work on the more casual end of the spectrum too. But I wouldn’t go too far—at least with a black leather pair—for fear of the boots not fitting the overall aesthetic. Leave these outfits for desert boots or sneakers.

My Chelsea boots are pretty slim and sharp, which I think goes well with my overall style. If you prefer a looser fit I’d definitely look for a pair of boots with a chunkier sole and maybe a rounder toe. I fear the ones I own would get overwhelmed if I wore them with looser fitting pants.

Skinny Jeans and Chelsea Boots

You can also get a variety of boot lengths. For my next pair, I’m on the lookout for ones that finish a little higher up the ankle so my jeans or pants can easily fit over the top of them. Or, I could wear them as a statement piece with pants rolled up. Either way, I think the ones that finish high have a lot to offer.

There are also two main ways of getting Chelsea boots on. Some pairs, like the ones in the images below, have an elastic panel that lets you stretch the boot’s opening as you put them on. This is a good place for embellishments and mine have navy elastic which is a nice touch. For a cleaner look, and probably one that’s warmer in winter, you can buy a pair that uses a zip.

Anyway, that’s enough from me. The rest of this article will show you how to wear Chelsea boots.

8 of My Favorite Chelsea Boot Outfits

1. Smart Casual With Indigo Jeans and an Oxford Shirt

Chelsea Boots Indigo Jeans Oxford Shirt

Chelsea boots, an oxford shirt, and indigo jeans is an outfit I wear all the time. It’s super versatile and works in many different situations. When wearing the boots with jeans I like to roll the cuff up so you can see the whole boot. While I’ve worn a blue and white striped shirt in the image above, the outfit would work with many different colors.

2. Chelsea Boots With a Sweater and Jeans

Chelsea Boots Sweater

You can easily throw a sweater on with jeans and Chelsea boots for a super simple yet stylish outfit. I like thicker, larger fitting sweaters the most.

3. With a Black Denim Jacket and Jeans

Chelsea Boots Black Denim Jacket

This is an example how Chelsea boots can take a casua outfit to another next level. I love the contrast between the jeans and jacket and the smarter boots. Wearing a black denim jacket rather than lighter shades is an intentional move as I don’t think it would work as well with a blue jacket. Happy to be proven wrong them.

4. With a Casual Shirt and Jeans

When wearing a jacket you should always ensure that what’s underneath works without the outer layer; you never know when you might have to take it off. I think this is definitely the case in the above fit. I love the silhouette created by the looser fitting shirt and the slim fit jeans and boots.

5. Keeping Warm With a Turtleneck

Chelsea Boots Jeans Turtleneck

This thick black and white turtleneck goes really well with the black Chelsea boots. I’m wearing blue jeans but it would go equally well with an indigo or even a black pair.

6. Or Even Warmer With a Leather Jacket

Chelsea Boots Leather Leather Jacket

Throw a leather jacket on over the top to complete the look. Despite the coat not being that thick, the turtleneck means the outfit is surprisingly warm.

7. With a Heavy Coat and Scarf

Chelsea Boots Coat Scarf

Here’s the outfit if you really want to stay warm. An overcoat, black jeans, and a scarf combine to create the perfect Chelsea boot outfit for winter.

8. Business Time With a White Shirt and Navy Pants

Chelsea Boots Trousers and shirt

I mentioned above that I don’t often wear boots with tailoring. But these are the one pair of trousers I make the exception for. They are super slim and finish at basically the exact spot the Chelsea boots start. The white shirt creates a really clean, sharp outfit.

9. Staying Dry with a Gray Overcoat

Chelsea Boots Overcoat

Here’s the same outfit as above but with a overcoat. I like the charcoal gray, but I think any dark color would work equally as well.

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Duncan Elder

Duncan is the founder and editor-in-chief of The Boardwalk. He's a menswear writer who has spent the last 15 years developing his own sense of style, which lies at the cross-section of mid-noughties indie and Uniqlo-inspired minimalism.

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