Where The Sidewalk Ends
Can you wear boots with a suit?
Short answer: depends.
Docs, cowboy boots or six-inch tall lace-ups? No.
Chelsea boots? Yes. (though I personally don’t care for them)
Chukka boots? …it depends on which one you pick.
Chukka boots with a crepe sole (the bottom looks like beeswax) are not appropriate with a suit. They’re great with denim and chinos, but not elevated enough to pair with something dressier.
Opt for something a little more polished, like this grey suede pair from Gordon Rush. The clean sole will go great with a suit and the casual shape lends perfectly to joggers or jeans.
And because they’re ankle length, you can wear them in Spring and Summer too. I’m already picturing white denim and a grey tee!
I find a lot of chukkas uncomfortable, but these have a cushioned insole and rubber treads. Clearly made to last! Thank God, cuz these city streets are rough on boots.
Find a great pair, and chukkas will be the most versatile boot in your closet. Hands down.