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Chukka Boots & Winter Suits 3 Ways

Chukka Boots & Winter Suits 3 Ways

Beckett Simonon Bailey Chukka Boots


There comes a point during the winter, when you get tired of wearing Oxford dress shoes to work (even with your suits). Since temperature has ranged anywhere between 5 to 58 degrees this winter and we’ve seen our fair share of snow, swapping out your Oxford shoes for a pair of sleek (but hearty) leather chukkas to pair with your heavier flannel suits is critical. You’re not going to need to run out and add 5 pair to you footwear line, but, you may want to opt for a versatile brown pair like these Bailey Chukkas by Beckett Simonon (available for $139. Goodyear Welt Soles). 

Style Tips For Adding Chukka Boots To You Winter Suits

  • No matter if their leather or suede, your boots need to have a sleeker silhouette to pair well with your suit. Remember, the goal is not to look like you’re wearing hiking boots with your well-tailored suit.
  • To cuff or not to cuff? It’s a matter of personal preference when deciding if a cuffed hem on your pants is best. Personally, cuffed pants complement chukka boots the best because of the added depth. If you’re a regular hem guy, they work just as fine. Investigate having your pants tapered some from the knee down, slimming you leg opening enough to showcase your shoes.
  • Suede or leather? This is another case of personal preference. Suede picks up on the texture of flannel suits better than leather, however; the contrast of a smooth leather is most comparable to you typical Oxford shoe (making it more business appropriate.
  • Try out your brown chukkas with variety of suits. You’ll be surprised that 90% of the suits (suit combo) you wear pair extremely well with these boots.
  • Don’t relegate your chukkas to just suit pairings. Rock them with denim and heavy-weight chinos too.


[tps_title]Dragon Inside Custom Grey Flannel & Beckett Simonon Chukka Boots[/tps_title]

Sabir Peele in Dragon Inside Flannel Suit & Beckett Simonon Bailey Chukka Boots

Custom Flannel Three Piece Suit – Dragon Inside | Vintage Knit Wool Tie | Custom “Ricky” Sunglasses with Blue Lenses by Lookmatic ($95) | Fall Into Spring Custom Gingham Shirt (Men’s Style Pro Design) – J.J. Threads | Pocket Square – The Tie Bar | Bailey Leather Chukka Boot – Beckett Simonon

Sabir Peele in Dragon Inside Flannel Suit & Beckett Simonon Bailey Chukka Boots

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Sabir Peele in Dragon Inside Flannel Suit & Beckett Simonon Bailey Chukka Boots


Beckett Simonon Bailey Chukka Boots

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View Comments (10)
      • Thanks for the effort! It is much appreciated. I like look 2 (although all three looks are impressive) the most, because it’s not your boring typical look. I like the fact you chose to add a bit of edge and pair it with a red vegan leather jacket. So much inspiration.

    • Hi Oscar,

      Thanks for dropping in and for the kind words about the looks! You dig lookmatic because of the freedom you get in the designing process for sunglasses and prescription glasses at a great price! Here’s a better look at the pair that I’m wearing in this feature.

  • i like this but i think black boots would be a little bit more attractive. but this is good too. Also check out some boots From boot barn coupons you might find something interesting.

    • Hi Johnsmith,

      Thanks for reading. When it comes to styling boots or shoes with your suits, if brown & black footwear is an option, you need to consider your other accessories (belt, watch and suit button color) to see what’s going to complement them best.



    • Hi Geetika,

      Thanks for dropping by. I’m a fan of the tan boots as well. Tan is usually my go to color. Decided to do a bit of a switch up.




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