footwear Style

Tips On How To Wear Chelsea Boots

Boots aren’t just for hipsters anymore. Men don’t have to be protesting the norms of current culture to love wearing something sturdy, useful, and fashionable. 

And thus the wardrobe of every man contains the perfect slot for boots of every type. 

But one boot is toeing its way into the hearts of male fashionistas everywhere: the Chelsea boot. It originated as a fashionable boot for artists and musicians in 1950’s London. And they showed up later as standard issue for Stormtroopers in Star Wars. The Chelsea recently returned as women’s boot, but Men are taking it back.

And yet, the problem lies in how one wears Chelsea boots. Can you wear them with your skinny jeans? How many kinds of Chelsea boots are there? Will they match with my leather jacket?

Scroll on down for answers to your questions on Chelsea boots for men.

1. Chelsea Boots for Men: What the Boot?

Chelsea boots are a formal shoe gone casual. You can find them now in all kinds of materials and colors from red leather to black suede. 

And the classic Chelsea isn’t just square toed. You can find pointed-toe Chelsea boots for men as well.

But before you begin pairing your Chelsea boots with a wardrobe, you have to know how to fit them to your feet. It should be easy, right? They have no laces.

And you are right, it’s fairly easy to fit yourself to Chelsea boots. But you have to find a balance between bunions on your toes and clown shoes. 

The best way to fit your shoes is to try them on in person. If you can find a store nearby, try them on there and then go online to buy the correct size. 

If you feel any squeeze in your toes at all, then these boots are too small. If you’re swimming in the shoes and your toes sashay when you walk, then you’ve probably got clown shoes on.

The Styles of Chelsea Boots

You’ve many options when it comes to Chelsea boots for men. What you choose could depend on your price point and your preference. 

Also, you have to consider what you’ll use them for. Are these stylish city boots you won’t ever want to get wet? Or are they winter boots to keep your little piggies dry?

And are you just trying to fit into a recent trend then possibly leave the boots as a dusty reminder in the back of your closet? Then you may not need to fret much over style and instead look at the price point.

Faux suede is fairly impressive despite its low price tag. While it won’t last long, if you’re looking to impress and trend for a short time, these typically $50 options would look stunning on your feet.

Pure leather is a material for those who want to adopt Chelsea boots permanently. To justify spending over $100 on a pair of boots, you have to be ready for commitment. It may not be a lifelong commitment, but you’re certain this relationship will last at least a few years.

Chelsea Boots and Your Jeans 

Jeans go with everything…almost. But do they go with your Chelsea boots?

Most certainly!

But you’re not forced to stick with merely blue jeans. In fact, the best boot and jean pairings match up black and black or tan and black. 

The 50’s Look

Fashions come back around and nostalgia hits an all time high at certain points in history. In the 80’s we yearned for the 50’s, and today the 80’s is rearing its head in the fashion industry

Filter that rad 80’s color out and you still have that 50’s motif shining through. And the Jimmy Dean look fits well with your Chelsea boots.

Kick it down Main street with a vintage leather biker jacket, a pair of black distressed jeans, a black or plain white t-shirt and your Chelsea boots. People will expect you to imminently roll back down Main St on your old Triumph motorcycle.

The Casual Business Look 

Can you pass off a pair of dark gray jeans as business wear in your office? We hope so because a pair of black leather Chelsea boots for men with a gray pair of jeans and tailored button along with a suit jacket will set you apart in the business world.

They’ll be too busy appreciating your incredible style to refuse your pitch. And what’s more, you’ll be comfortable while you give it.

The Day Off Look 

Just because your boots work well at the office doesn’t mean you can’t wear them on the street. If you spent good money on your boots, you want to get the most use out of them as you can.

A pair of sleek boot-cut navy blue jeans slightly rolled at the ankles should do the trick. Pair these with either brown leather or black Chelsea boots for men then top it all off with a denim shirt and you’ll be casually awesome all day long. 

Some Things to Consider About Chelsea Boots 

There might be a few things you don’t know about Chelsea boots. Hey, we’re not all perfect!

But we’re here to fill you in a little. Here are some last minute considerations about our new favorite boots:

  1. Chelsea boots don’t have zippers. If there’s a zipper, they’re not Chelsea boots.
  2. Leather is classic and traditional. We recommend it. But don’t feel it’s your only choice.
  3. When choosing your Chelseas, look at the elastic. Is it taut? Only quality elastic is taut.
  4. Don’t rely on standard shoe sizes. The only part of the shoe that’s elastic is…well…the elastic. Get fit in person first. 

Conclusion: No Regrets

Whether you’re buying Chelsea boots just for formal occasions or you want them as your everyday wear, you won’t regret buying a pair. They’ll last you for years and they pretty much go with anything you wear. 

If you’ve already made up your mind and want to buy a pair now, check out our selection. We’re sure to have your size on hand.

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