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  • Price $450 on
    Use code ALEXKWA for $75 off.
  • Handmade in Italy


Having studied countless brands and their origin story, it almost always starts when the founder(s) gets so dissatisfied with the option in the market that they decide to make their own. The Rakoh story is the same. It started when Raphael, the founder, couldn't find a pair of shoes that would be comfortable enough for urban adventures yet look good enough for a business meeting or event. So much so that he decided to make one himself.

If there is no one I can relate to better than a person obsessed about their stuff.

Having dived into the world of the good year welt, there are plenty of boots that look amazing and feel comfortable, but certainly not sneaker-level comfortable. Rakoh looks to change that.

As a remote worker and designer, I've never been subjected to office dress codes. Shorts and t-shirts were a usual sight on creatives in ad agencies in Singapore. In Japan, even where suits are a common sight on trains, I've never been part of a company that had any dress code. I probably wouldn't join a company that had one—fun fact: I've never worn a suit for work.

However, this doesn't mean I won't dress smartly even if I don't have to. When heading into the office, I often throw on nice-looking pants like the Outlier Futureworks and the Wool&Prince Shirt. For footwear, I default to premium-looking sneakers like the Kent Wang Handgrade Sneakers or Everlane Tread Trainer. However, these are still casual footwear.

The Rakoh is a premium pair of boots that caught my eye for how great it looks, ideal for completing my office wardrobe.


The Chelsea Boots isn't an original style by Rakoh. It actually has quite the history. In the 19th century, Queen Victoria often got the boots laces entangled in her stirrup, so she asked the royal shoemaker, Joseph Sparkes Hall, to invent comfortable footwear that could be put on and off without laces.

With the Western Rise Evolution Pants, and Rakoh Chelsea Boots.

From royalty, the style found its way to workwear and even the military. However, these shoes didn't have the name “Chelsea Boots” all the way up to the first half of the 20th century. Up till then, the inventor, in his patent, called it the “J. Sparkes Hall's Patent Elastic Ankle Boots.”

With the Outlier Strongshank, Western Rise Evolution Pants, and Rakoh Chelsea Boots.

In the mid-1950s, one of the first cafes to serve espresso, the Fantasie Cafe, opened on 128 Kings Road, a street in Chelsea. The cafe drew a hip clientele to the neighborhood of Chelsea. This collection of designers, writers, bohemians, revolutionaries, artists, and the likes became known as the “Chelsea Set.” The Chelsea became such a trend that hardly a day went by without the media mentioning the name. The boot that this eclectic group of creatives wore, by association, got the name the “Chelsea Boot.”

Since then, the boots have graced the feet of countless legendary rock'n'roll bands, such as the Rolling Stones, Velvet Underground, and The Beatles.

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The Chelsea Boot was meant to be a close-fitting ankle boot with an elastic side panel, and that's certainly what the Rakoh Chelsea Boot is—true to the original design.

Like the original, it comes with a tab on the back for you to pull on it as you slip your feet in.

While Rakoh has released suede versions of the boot, the leather one is the most beautiful to me. The exterior of the boot is completely black, while the interior is of natural leather brown.

There is no visible branding, and the only branding on the exterior is a logo on the rubber sole.

The logo is also on the insole.

The boots are true to size. You should get your usual size and size up if you are in between sizes. I am usually a US10.5 for sneakers and got a size 46. This was actually a mistake, and a size 44 would have been the appropriate size for me based on Rakoh's size chart. While the size is a little large, it actually didn't feel too large. Now that I've tried the size 46, I feel that size 45 (US size 12) might be better than the size 44 (US size 11).

For a design that's so true to the original, there is little to fault with Rakoh's take. The classic silhouette, elevated by premium Italian leather, is beautiful. It works well with any clean-looking long pants, like the Outlier Slim Dungarees. Even though it has military roots, I won't try it with a pair of fatigue pants.


The boot is handcrafted in Italy with Italian leather. In line with making sure the boots are comfortable, the leather is buttery-soft and requires no break-in.

I designed a thing.
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I found a 100 year old company that would create these heirloom quality canisters for me. They are handmade and will keep your tea leaves, coffee beans or anything that you need dry for years to come.

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The insole has 5mm of padding for added support and comfort. The thickness of an insole has the ability to affect the contact surface area formed on the sole of the feet. The thicker the insole, the more the surface area and the higher the stability. However, after a certain threshold of about 10mm, insoles that are too thick will push the foot out of the shoe and cause more instability.


With the design based on the original and price not too far off from Chelsea Boots from other brands, the comfort of the Rakoh Chelsea Boot seems to be the main selling point.

They tout a thicker 5mm insole and soft premium leather that will eliminate the need for break-in periods. A boots break-in period is the biggest put-off for me, and this almost sounds too good to be true.

I'm glad to report that the claims are true. The Rakoh Chelsea Boot feels as comfortable as a worn-in pair of sneakers. On my first day wearing it, I wore it for a total of 12 hours around Tokyo. The feet were fine, thanks to the cushy insole.

However, the boot rubbed onto my calves the whole day, and it felt a little sore. While socks of appropriate length could easily remedy this, I've started wearing only one type of socks, the Darn Tough Tactical 1/4 Socks; it doesn't quite cover enough of my calves to do that.


Rakoh's rendition of the iconic Chelsea boots is flawless. Then again, the original design of the boots was flawless and Rakoh did a brilliant job in keeping true to it, elevating it with premium materials and ultra-comfortable insoles.

In all honesty, I don't have another pair of Chelsea boots to compare this with, but if all Chelsea boots were as comfortable, I'll be definitely owning a few more.

Sold? Remember to use the code ALEXKWA at check out to get $75 off your order.


  • Effects of Using Insoles of Different Thicknesses in Older Adults Which Thickness Has the Best Impact on Postural Stability and Risk of Falling?

Additonal Images

With the Airinum Lite Air Mask, Outlier Strongshank, Western Rise Evolution Pants, and Rakoh Chelsea Boots.
With the Outlier Strongshank, Western Rise Evolution Pants, and Rakoh Chelsea Boots.
With the Outlier Strongshank, Western Rise Evolution Pants, and Rakoh Chelsea Boots.
With the Outlier Strongshank, Western Rise Evolution Pants, and Rakoh Chelsea Boots.
With the Outlier Strongshank, Western Rise Evolution Pants, and Rakoh Chelsea Boots.
With the Outlier Strongshank, Western Rise Evolution Pants, and Rakoh Chelsea Boots.

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Tagged boot footwear review shoe