How To Casually Style Chelsea Boots

Akil McLeod Dapper Advisor Sebago Chelsea Boots Leather Jacket Denim 1

Chelsea boots have easily become one of the most popular boot styles over the past 2-3 years. It’s similar to when double monks hit the #menswear scene and everyone started buying several pairs at a time, including me. The interesting thing about chelsea boots is that although they are extremely versatile, it really depends on the silhouette of the shoe that determines how the shoe should be worn.

For instance, these chelsea boots from Sebago are definitely a more casual option because of the slightly rounder silhouette. As opposed to my other suede chelsea boots, seen here, that I usually wear with suits and tailored trousers due to their sleeker silhouette.

Akil McLeod Dapper Advisor Sebago Chelsea Boots Leather Jacket Denim 2

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When it comes to casually styling chelsea boots, the most important aspect is wearing the right jeans. In fact, I’m actually wearing the same jeans from my collaboration with the Thursday Boot Company because a lot of the same rules apply here as well. Additionally, since chelsea boots have an elastic band on the sides instead of laces, it is essential to make sure that your jeans have a slim taper so that it can sit comfortably over your boots.

Akil McLeod Dapper Advisor Sebago Chelsea Boots Leather Jacket Denim 3

Style Tips:

  • Make sure your jeans are tapered and hemmed, roll them up if necessary.
  • Raw/selvedge denim is my preferred denim of choice, especially for black or brown chelsea boots.
  • Chelsea boots with rounder silhouettes should be worn with jeans while the sleeker silhouettes should be worn with tapered trousers.

Akil McLeod Dapper Advisor Sebago Chelsea Boots Jacket by Adriano Goldschmied, Shirt courtesy of Handvaerk, Jeans by H&M, Shoes courtesy of Sebago

Thanks for reading!

Yours truly,

Akil McLeod
The Dapper Advisor 


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