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How to Wear Chelsea Boots: Men’s Style Guide

This post is brought to you by KIWI and their #WalkWithPride campaign.

Have you ever heard of Chelsea boots? Maybe not. Although the name may only be reserved for those who are either extremely into fashion or take their boots seriously, there is no denying that you’ve probably seen a pair of these on your favorite celebrity a time or two.

The name goes back to Queen Victoria’s shoemaker, J. Sparkes-Hall, who originally designed and patented the shoes in 1851, and were originally designed with women in mind. That all changed in the 50s when they came stateside thanks to a British Invasion.

In addition to discussing the history of the Chelsea boot, we’ll also go over a number of outfits that look best paired with them.

I know that when I spend $500 on a Chelsea Boots, I’m definitely going to go the extra mile to protect them. That’s why I use and recommend KIWI Protect-All to keep my boots looking fresh for years to come.

In New York, we don’t get that much snow, but what we do get a ton of is salt. No, not table salt, but the salt they use to break up the ice. As any New Yorker knows, this salt is a nightmare on your shoes.

Whenever I get a new pair of boots, I spray a couple coats of KIWI Protect-All, so that when I encounter rain, snow or salt, I know my boots will be protected.

This Is My Story and How I Walk With Pride As The Founder of Life, Tailored

I started Life, Tailored in 2013 with the goal of sharing my love of the best things in life with my friends.

But my story begins way before I came to New York and launched Life, Tailored. I went to school in Florida, and after graduating, I stayed an additional 4 years. It was an easy life, I lived in a college town, and enjoyed 4 championships while I was there.

But I wanted something more. I had always dreamed of living in New York, and living the big city life. Part of that life is learning about how to dress like a New Yorker (and how to protect those investments with great brands like KIWI).

Prior to Life, Tailored I had only traveled internationally to the Bahamas on a cruise. Today, I’ve been to more than 15 different countries, and have flown First Class to those countries paying for them just with airline miles.

My fascination with first class travel happened on a routine trip to Orlando. My wife and I had our flight cancelled, and had to rebook in the morning. When rebooking, we had the option to upgrade to “First Class” for just $60. We went for it.

And as soon as we got on board, we were hooked. I told her that 1 year from now, I’m going to figure out how we can fly like this every time.

Now, when I fly, I feel like a million bucks. I wear my killer outfit, get to relax in the lap of luxury, and know that I was able to do it all through sheer dedication and hard work.

I hope my story is inspiration to give you the confidence to know you can do anything you want in life, and it all starts with preparing yourself for whatever life throws at you.

And if you have a pair of killer Chelsea boots, consider KIWI as your first line of defense.

How to Wear Black Chelsea Boots with a Long Coat



As a shorter guy, I love that Chelsea boots give me a little extra height. That extra height definitely comes in necessary when you wear a long coat. Unless you’re 6 feet plus, a long coat is going to make you look shorter, so pairing your car coat with a pair of Chelsea boots is the perfect compliment.

These black Chelsea boots really do go with anything, but look great with the grey color in the oat.

How to find your perfect Chelsea boots

As previously mentioned, Chelsea boots have that versatility to fit into any wardrobe to work with nearly any outfit.

Before you run out to the store and purchase hundreds of dollars of unnecessary clothing items to match your latest edition Chelsea boots, there are a few things that you should know about the shoes themselves:

Chelsea boots should fit snugly and not too tight

Comfort is always key when it comes to everything we wear. This is no different for Chelsea boots, I will tell you right here and now that they are undeniably enticing to wear because of their slip-on and smooth feature. However, this can cause irrevocable damage to the shoes themselves. You want to make sure that the shoes are a perfect fit; not too tight and not too loose.

Chelsea boot design has evolved since their original creation

Chelsea boots are designed with either brown or black box calf leather and leather sole. With the rise of talented and innovative designers, what was once the traditional design of Chelsea boots evolved to a style that is now considered more sophisticated men’s footwear. Some manufacturers have even come up with new shoe designs inspired by these boots under different naming for their own branding purposes. Basically, Chelsea boots are made up of commando soles, Jodhpur/Zip ankle boots, and broguing or wingtips.

Chelsea boots in suede pair really well with a suit

Leather-made Chelsea boots are great to wear because they are versatile and durable. However, nothing comes close to the elegance that the suede boots give. They may have higher maintenance than your leather boots, but they are definitely worth investing.

Chelsea boots can be suede and also rugged

It’s true when they say that there is more to simple things. Like in the case of Chelsea boots, the simpler the design, the more beautiful the boot. It has been proven that boots with simpler designs are always better.

How to Wear Chelsea Boots: Men’s Style Guide

It’s not enough that you only have the knowledge on the footwear that you are going to use. More importantly, you should know how to flaunt and pair them with. Why is that so? Well, simply because Chelsea boots are admittedly the type of footwear that has an elusive style. Good thing that what has been a monotonous way of wearing them was maximized to a couple of clothing styles to match.

Typically, the general rule for wearing them is to have your pants cover the top of the boots. Unlike the Chelsea boots, there are other boots that you can wear with an uncovered top. You may also want to drape the entire neck of the boots and it’s fine. Just a rule of thumb, make sure to check the style if it works on you before breaking it.

Wardrobe-wise, here are some ways on how to rock your style with Chelsea boots.

How To Wear Chelsea Boots With a Suit

Most of you think of pairing your suits with loafers, Oxfords or brogues but Chelsea boots are another great option. The wide variety in terms of colors, finishes, and materials give you a range of suits that would fit these boots. Have you tried matching your gray suit with a pair of black leather boots?

If you are more into wearing blue or navy colored suits, having a pair of brown leather Chelsea boots completes the overall look. These are two contrasting colors that make a harmonious ensemble. Applying the general rule of covering the top part of the boots leaves you with that smart, clean guise.

How To Wear Chelsea Boots With Jeans

These days, who says that sneakers are the best thing that happened to jeans? Well, try to wear your jeans with a clean shirt, a jacket, a polo shirt, or a blazer. You may even have a combination of these for your top. Do you think they will not look good with your leather boots? We do not recommend otherwise. For your jeans, it is best to go for a pair of suede Chelsea boots.

You may start by going with monochromatic or understated colors. You may mix of a plain white shirt, a classic leather jacket, and a pair of gray or tattered jeans. Completing the look with a suede black Chelsea boots pimps you to a smarter, more casual look. If you are not into suedes, you can always go for that synthetic pair. You may opt for a broader option of reds or purples for your pair of black skinny jeans as well, to add that extra pop of color.

How To Wear Chelsea Boots With Cuban Heels

The timeless Cuban heel boot, a type of Chelsea boot with the Cuban heel, completes The 50s era. To look perfectly good with this kind of boot, your trousers have to be at an imperatively accurate length. How do you ensure the proper length of your trousers for your boots? This may sound funny and awkward, but you have to bring your trousers with you during the purchase. This is needed to avoid unintentionally showing your ankles when wearing them.

Do you think you’re ready to take part in the Chelsea boots fashion? There is nothing to be afraid of. Just look at the style guide we have for you and you will surely rock the style!

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities. Lifetailored has partnered with Creditcards.com for our coverage of credit card products. Lifetailored and Creditcards.com may receive a commission from card issuers Additional Disclosure: This site has affiliate links. We may be compensated when users make a purchase or register to a third party website. For more details read our privacy policy.

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