Reboot your Footwear with Chelsea Boots


The British have contributed heavily to the world of men’s fashion for centuries with staples that still hail supreme today such as tweed, trench coats and the blessed three piece suit, but this season, Chelsea boots have been the toast of men’s footwear and my personal new favorite shoe of all time.

Taking its roots from Victorian England just as another area of style, Chelsea boots began as an innovative go-to footwear option for walking and horseback riding with its then original, patented elastic side panels made to provide easy access in and out of the shoes. Queen Victoria may have favored these kicks but it wasn’t until the Paul McCartney and John Lennon adopted these slip on boots that the world of men’s fashion took notice.

Since then, rock-stars, rappers and everyday dapper gents alike have been rocking these shoes past the brink of trendy to become a footwear staple made easy by the versatility of these boots. So without further adieu, allow me to walk you through the range of rocking a pair a Chelsea boots like the style bad-ass you soon will become.

Casual Like Kanye


Yeezy is currently one of the most talked about figure in pop culture thanks in part to his polarized fashion label named after himself of course, Yeezy.  For most of his career, Kanye has been praised for his eclectic sense of style, being featured in menswear magazines across the globe and emerging on the best dressed list of these same coveted magazines such as GQ, Esquire and Detail magazine.

The self proclaimed Yeezus stirs up controversy with his God Complex and outlandish behavior at award shows and radio interview and probably at grandmas house but one thing is for sure, he knows how to rock some Chelsea boots lie he invented them himself!

Search online and you will see quite a few pictures of Kanye wearing my new favorite shoe, one of my favorite look is the one pictured here.

This is a prefect example of how to pull off a Chelsea boot in a relaxed setting as their is nothing else more laid back than a t-shirt and jeans except maybe a t-shirt and jogger pants but I’m afraid I must insist against pajamas in public, I WILL find you!

This picture caught my eye because of that fantastic overcoat that IS this outfit but the shoes pose a focus of their own. An age old rule of thumb in the style department is to avoid wearing black and brown together in the same outfit but their is always a grey area (pun intended if your a goofball).

I think the chalky brown boots work in this look because the grey tones stand out more than the subtlety of the black tee shirt and the faded hue of the shoes merge more easily into the medium grey shade of the pant creating a look that say go f**ck yourself to the anti black and brown rule.

Suede is a great choice in material for an everyday look and it adds a further level of texture as it does in this look with the aid of the wool texture of the black and white nail-head coat Kanye is donning.

Get a pair just like the ones worn in the picture that Yeezy himself would obviously approve of right here.

Styling with Styles


As a member of the world currently most popular by boy band, Harry Styles is a well known figure but his sense of style gives a claim to fame aside from his fellow One Direction comrades. Styles dresses in the exact way you would expect a modern day rock star to dress but his style doesn’t look reclaimed from the Rock-gods of yesteryear but a look that is completely self identifying. What brings him here o to the cyber pages of The Gentlemen’s Ledger is his favor towards our wonder boots.

Harry Styles has been photographed in Chelsea boots so much that I’m surprised their isn’t a scarcity reported in the U.S. and the U.K. but if there were, he’d still have access because well, he’s Harry Styles. Whether dressed for a fashion show or a paparazzi filled walk on the streets of New York, style is donning a set from his army of Chelsea boots to tackle the daunting demand of fame in relaxed swank.

As an outwear idolizer, the present picture of Harry stood out because of the forest green military coat. This coat acted as the centerpiece of the muted tones that make up this look. The suede fabric of the coat adds that texture that I rave about while the addition of the texture of the scoop neck sweater further enhances the look.

A black pair of jeans can go a long way and these act as the perfect backdrop for this laidback ensemble. But of course, just as a shoes is intended, the boots ground the whole look and add an extra level of visual intrigue.

These boots look best with tailored or slim fit pants but a great way to make these boots stand out even more is to take the same avenue as Mr. Styles and gather the hems of your pants along the opening of the boots. This shoes of the boots in their entirety and presents any details that they may have such as the buckles on my very own Chelsea boots.

Suited and Booted

What’s more dapper in the world of menswear than a suit? As the armor of the modern day gentlemen, the suit in its current look has stood the test of time with the help of small tweaks to the design and the accessories paired with these pillars of menswear.

With tweaks in mind, Chelsea boots create an elegant edge to a classic tailored look. It gives off a laidback vibe to an in charge look that you see in the boss’s son whose outfit says, I’m trying but not to hard….. because I don’t have to.

Get a pair just like the ones in the photo here.


Keep in mind that your suits aren’t just for work, weddings and formal occasions, these liveries can be worn on an off duty bases that takes your suit from boardroom ready to happy hour fit.

Try intermingling your suits in with casual pieces rotating the jacket and pants into different look but also wearing the suit as a whole with a casual top like a polo, crew-neck sweater or my personal favorite, a turtleneck.

Whether it be in a chunky sweater or slim shirt form, a turtleneck under a suit will give you a suave nonchalance that the Italians call sprezzatura.

One interesting thing you will notice about the turtleneck look is the footwear worn. If you look closely enough, the Chelsea boots featured aren’t boots at all, they are actually Chelsea sneakers. All the sleekness of the Chelsea boot with the comfort and snappy finish of a sneaker.

The style studded innovation was obviously destined to grace this post because I actually happened upon a pair of these Chelsea sneaker here and was pretty impressed. Designs like this are so simple that it makes me wonder why I didn’t come up with it and the equally simple answer is that I didn’t try. Maybe in the future, I will create pieces that will dazzle and amaze from a simple but radiant design but for now I’m perfectly happy discussing such pieces from titans of the style industry until I join their ranks.

Your shoes are the foundation of any outfit you wear so your footwear choice can make or break your look. Therefore, If there is any single areas to make an upgrade in style, your shoes should be one of them and having a pair or tw…. seven in your closet will put on the right tracking to boosting your footwear game and the rest shall follow.

6 thoughts on “Reboot your Footwear with Chelsea Boots

  1. fashion has changed so much over the years, but i like the way they are going with it

    All of these shoes look pretty stylish and I definitely could see me rocking a few of them in particular!

    Thanks a lot for the article and I will be sure to revisit in the near future

    1. Hell yeah you could rock these, in fact I insist that you do! Thanks for stopping by and i hope you do come back for more and start rocking some other looks as well.

      All the best,


  2. Hello Tony,

    Must be my day for shoe shopping haha! I just bought a pair of gym shoes earlier but need something a bit fancier as well. Your article here about the Chelsea boots has me really excited for some new boots. I think the more formal black would be great for taking my lady out on the town. BUT I do agree the rugged looking ones Kanye is wearing look pretty sick too.

    Take care,

    1. Hey Ant, I hope your cool with being called Ant because I’m sticking to it. I’m glad you happened to be looking for shoes and looked at this article because Chelsea boots are one of, if not the most versatile shoe that a man can own so I urge you to go in this direction as opposed to any other style. You get a lot of wear out of them in a wider range for occasions therefore saving a few bucks and your lady will think your a stylish piece of ass which is the ultimate plus.

      Happy shopping Ant and thanks for reading!


  3. I love the Chelsea Boot, quite a fashion statement essential 🙂

    My 17 year old Son often talks about “Yeezy”, of course he had to explain who he was talking about, my Son does like to follow his fashionable key pieces and I have no doubt that it will include the Chelsea Boot.

    One of my other Sons are getting married this year and is thinking of wearing a high shine version of this boot with his suit, do you think that it will deliver on style for this occasion?

    Personally, I think that this style of boot is great for all ages 🙂

    1. Hi June,

      Congratulation on the nuptials of your son s well as having two men of style to claim as your own. Yes, I think your son’s idea of wearing chelsea boots on his wedding day is a great idea. That will add a little spice from the traditional wedding regalia and show off more of his personality. Thanks for sharing your thoughts!

      ~ Anthony

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