This week, I wanted to write about the Chelsea boot. This classic in footwear is a great fashion piece in today’s trends. I’ll cover the basics of choosing the right boots, as well as how to pair them in a formal and casual setting.

Basic guidelines when buying Chelsea boots:
  1. Material: Whether it’s leather or suede, make sure the quality of the boots are good. This piece is a bit pricey so you don’t want them to fall apart two weeks after purchasing them.
  2. Fit: You obviously want to be comfortable! This means that your feet shouldn’t rub against the sides of the boots. Comfort and style go hand-in-hand.
  3. Match your style: Chelsea boots come in a variety of styles. Some more rounded at the toe, while others have that narrow point. Choose what suits you best.


  • When you decide to pair Chelsea boots with a suit, you want the trousers to sit perfectly.
  • The leather option is great for formal wear, as it looks classy and compliments the style you have chosen.
  • Black, suede Chelsea boots also allow the broken suit look to come across as dapper.


  • Black leather or suede boots pair perfectly with a grey or black suit, while brown boots better compliment light blues or navy.
  • The colour tone of the boot for the light blue or navy suit are important.


  • Pairing the Chelsea boot with jeans provides a unique style that will allow your outfit to pop.


  • Rolling up your jeans to sit just perfectly above the boot is trending and necessary to make this style work.
  • Blue jeans and a button down shirt pair well with brown suede or faux suede boots. Include a bow tie to up your game if you’re feeling a bit more semi-formal.


  • Alternatively, black jeans with a t shirt and a bomber, paired with black suede Chelsea boots gives you a casual look for the day.

Chelsea boots are a timeless piece that work in any setting. Mix and match different pieces, t-shirts or dress shirts, jeans or a suit. Whichever decision you make, the Chelsea boot will complete your outfit without fail. So be creative!

For more style ideas, check out my Instagram page @dysfunctionalwardrobe.

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