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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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