How to wear Chelsea Boots

How to wear Chelsea Boots

The Chelsea boot is versatile, edgy and fun. It’s no surprise that a lot of global fashion influencers have chosen it as their go to shoe. In fact, at one point I thought Kanye West had more Chelsea boots than Yeezys and for a good reason! The shoe has been rocked by The Beatles and that catapulted the shoe’s popularity. Other worthy mentions are David Beckham, Tom Ford, Harry Styles and Olivier Rousteing among several other big names that rock the shoe every now and then. How about Queen Victoria who rocked the boot in 1837 as her bespoke riding boot that started it all? Well, we can go on and on about the shoe’s legacy but the important question is – have YOU tried the Chelsea boot? If not, I sure hope to change that.

Dr. Martens Chelsea Boots


The Fit

A Chelsea boot forces you to wear it perfectly. If you wish to walk around like an ostrich, it’ll make sure that you do. Yes, it is an unforgiving fit. Since it’s a laceless shoe, it should fit snug, not tight because unlike a laceup shoe, you cannot compensate for a loose fit by simply tying it around to stay on your feet. It’ll either fit you or it just won’t. This simply means neither should the shoe be pushing your toe back, nor should it rub against the sides of your feet. If it’s too big, it’ll look like you’re trying to stick two matchsticks into a pumpkin. Too small, and it’ll feel like you’re trying to bully a 3-pin wall socket with your socks on! Proper fit is essential, so I highly recommend trying a pair out in person if you’re feeling a bit dodgy about the online options. But if your new smartphone is attached to your thumb, start with a conservative size and go up from there. The one simple rule that you must follow at all times is that your pants should cover the neck of the shoe entirely and yet, should still stack on your leg.

Women Chelsea Boots Red

Materials & Brands

Leather and Suede are the two most common variants you’ll find for this minimalist shoe and in all honesty, those are the only ones you really need. Of course you can play around with the colors but you can never go wrong with black and brown which can easily sail you through all the important occasions. Some color options may include grey, tan and navy for men but it’s all about personal preference. Women can be a bit more liberal with colors – oxblood, olive, charcoal grey, red, etc. are all game. If you have the dough, you can go for higher quality Italian leather and suede variants from designer labels but as a rule of thumb, I usually stick with a manufacturer that I know has been creating shoes for a while for a bang-on overall composition. The options are endless from Hush Puppies, Ruosh to Nine West, Steve Madden, Prada and so on.

Mr. Porter Chelsea Boots Suede


Dress them up, Dress them down

You cannot deny that the upkeep of an all-leather shoe is much easier compared to that of a suede shoe. Equally undeniable is the fact that suede feels more luxurious, understated and elegant. You can wear your leather Chelsea boots easily with a suit, while keeping in mind the black and brown conventions (not rules!). On the other hand, you can rock the suede version when you want to come across as someone more stylish and the list includes denims and chinos. For women, a heeled Chelsea boot can be easily worn with regular or distressed denim for the ultimate urban chic look. Regular low top non-heeled booties work wonders too.

Taft Jude Boot


The Chelsea boot is one of a kind. It’s sleek and minimalist, it’s versatile and fun, it’s quite edgy and catches the eye easily. Shoe lovers who swore at one point they would never touch anything laceless have embraced them. I know because I was one of them! It adds a tasteful underline to an on-point outfit or makes it on-point by just being there. Chelsea boots add a flair that your oxfords and derby brogues just don’t. Go ahead and just try one.

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