But what we will say is that chukka boots are an incredibly versatile style of footwear that you’ll definitely get a lot of use out of year-round. That is, as long as you know how to wear them.

If you buy something through my links, I may earn a commission. Boots are always my go to as the temps start to drop, ...

Why Trust Us? The sole of a chukka boot impacts how comfortable it feels, how long it lasts, and where you can wear it. Here's a breakdown of the two main options. A natural rubber with a soft ...