Chelsea or Chukkas: The Eternal Dilemma

December 25, 2021

Chelsea or Chukkas: The Eternal Dilemma

With the mercury level dipping further each day, Mother Nature is already signifying the advent of chilly winters. And how’s winter even complete without the quintessential long coats, a mug of hot chocolate, and a pair of elegant boots?

As far as winter fashion is concerned, we’re pretty sure that your wardrobe is all set to rock the upcoming festivities. But what about your shoes; are they all set? Well, your pause confirms that it’s a no. In equivalence to the attire, men’s footwear is unquestionably a prominent item that captivates the world. Plus, they complement a man’s entirety in such an effortless manner. 

Speaking of upping the footwear game for men, year-round styles like Men's Leather Chelsea Boots or Chukka boots are what most men seek with approaching winters. Hence, owning one or both of these styles is an absolute must! But, alas, it’s a clash between the best. Often, even the most fashion-educated men find themselves entangled in the dilemma of choosing between the two very chic styles. After all, each one has its distinct edge over the other. And that leads us to quite a pertinent question - what are the differences between Chelsea and Chukka boots? Moreover, how can you style them? 

Captoe Chelsea Boots - Croc Tan

Well, to clear out this mess, we’ve collated a smooth guide right here that will help you choose the best version for yourself.

Knowing the finest: Chelsea & Chukka

Before diving into the intricacies, let’s first learn the preliminaries.

Chelsea: Traditionality at its best

First designed by J. Sparkes-Hall, Queen Victoria’s personal shoemaker, this supremely elegant style rose to popularity in 1960’s Great Britain. In certain places, they were also referred to as J. Sparkes-Hall’s Patent Elastic Ankle Boots. Chelsea boots were even related to King’s Road which is a street in Chelsea. And with the aid of the Rolling Stones and Beatles, they conquered the boots industry like no other.

Rising no further than ankles, Black Chelsea Boots are made of the usual hard leather or suede along with their iconic elastic gore panels on either side which secure the foot with the boot instead of laces. Some of them even have a pull tab at the heel. They have primarily two styles - a bulkier English style with a wider profile, and a more rounded toe box, and a slenderer European style with a shallow instep and a narrow toe box. Also, prepare to be blown away by the variegated color options that Chelsea boots offer; Wine Red, oxblood, blue along with the basics brown, tan, grey and black - you name it and you have it!

No wonder, they are considered to be one of the most stylish options when it comes to boots!

Chelsea Boots

Styling Chelsea boots

Now that you know the historical significance and basics of Chelsea boots, here are some style considerations for you:

  • Formal look - Nothing like black or brown Chelsea!
  • Semi-formal look - Brown Chelsea Boot with a blue suit or Black Chelseas with a black or grey suit
  • Business casual- Dark suede or matte brown

Remember to wear your pant cuff past the opening of your boot to avoid messiness.

Chelsea boots - Yays!

  • The elastic sides enable easy to slip on and slip off without bands or clasps.
  • Chelseas are strongly built. Therefore, they last for decades.
  • Highly versatile
  • Not to forget, of course, the clean silhouette of Chelsea boots. No lace, no mess!

There isn’t any downside for Chelseas, but for somebody who doesn’t like pull-up tabs, we don’t recommend this style.

Chukka: Fashion at its peak

Also known as turf boots or desert boots, Tan Chukka Boots too have a rich history. It is believed that the name ‘Chukka’ was derived from the word ‘chukker’ which is seven-minute period of the polo game. And with the onset of World War II, Chukka boots were widely used by soldiers. Consequently, they went on to become an intrinsic part of an Englishman’s wardrobe in the 1950s.

This refined style of dress boots captures our hearts with its classic plain toe design, open lacing system, and simplistic ankle-length cut. The minimal lacing, again, is an implication of the limited height of the Chukka boots. It’s this very simple yet edged style that makes Chukka boots perfect for any event!  Being crafted from suede or calfskin, they’re more durable in the colder months.  

Chukka Boots

Styling the Chukka Boots

  • Avoid opting for any color clashes; instead choose a suitable color of trousers with the boots.
  • For a funky casual outfit, pair basic shaded Chukka boots with patterned socks.
  • For the trendy winter-man in you, go for oversized jackets and knitwear with dark jeans, smart jackets, and brown chukka boots.
  • For the geeky look, go for a brown Chukka boot with a mid-grey or navy suit.

Chukka Boots - Yays!

  • Hands down, they’re so versatile! Be it any occasion or any outfit, a pair of chukka boots and all the eyes are bound to be on you.
  • They can be customized with slender bands.
  • You can go sockless with chukkas because they tie up very near to your lower legs.

Much like Chelsea boots, Chukka boots shouldn’t be bought if you want a hefty boot or a work boot.

The verdict

Having read so far, you must be utterly confused about how to choose between the two. But here’s what we think in a nutshell-

  • Chelsea boots are cool casuals but more formal. Whereas, Chukka boots are more casual and less formal.
  • Chukka boots are lace-ups; Chelsea Boots are slip-on.

Both the styles are therefore highly advantageous; both can compliment casual and formal outfits. Considering the flexibility, however, we strongly recommend investing in a pair of Chelsea boots. But then again, they are on the higher end of the price tag. Hence, the best solution to your incertitude is - get your hands on both of them!


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 All our shoes are designed to match standard UK & US dress shoe sizes. However, to ensure the perfect fit, please go through below size chart:




Approx. Foot length in cms

Approx. Foot length in Inches

5 6 39 23.3 -23.9 9 2/8.6- 9 4/8
6 7 40 24.2 -24.8 9 5/8 -9 7/8




25.0 - 25.5

9 7/8 – 10 1/8




25.8 - 26.3

10 1/8 – 10 3/8




26.5 - 27.0

10 3/8 – 10 5/8




27.3 – 27.8

10 6/8 – 11




28.0 – 28.5

11 – 11 2/8




28.7 – 29.2

11 2/8 – 11 4/8




29.5 – 30.0

11 5/8 – 11 7/8




30.2 – 30.8

11 7/8 – 12 1/8

 For a correct shoe size, please take the time to measure your foot. 

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