I’ve named them the best overall Chelsea boots for their wearability and iconic style. Not only are they sleek, they’re comfortable enough for long days on your feet (my dad used to wear a ...

Below, I'm highlighting the 32 best winter boots to wear with jeans, from leather riding boots to chocolate ankle boots and chic suede options. Talk about versatile shoes. A personality buy.

Barrel jeans are not intuitively chic. Their shape and distinctly bowed-out legs feel foreign, and they seem a little intimidating to wear ... Tabi boots, Doc Martens, or classic Chelsea boots.

You could wear these with a suit, jeans, cargo pants ... these are some of the best value-for-money Chelsea boots on our list. Cons: Similar to the Paul Smith option, these are not the best ...

Chelsea boots are trend proof, which makes them an investment you’ll never regret. The permanence of the Chelsea boot has a lot to do with comfort and ease. It’s a slip-on style with a low ...