— Recommendations are independently chosen by our editors. Purchases you make through our links may earn us and our publishing partners a commission. Pretty much everything that was cool in the 90s ...

When you buy through our links, Business Insider may earn an affiliate commission. Learn more Once you've broken in a solid pair of Chelsea boots, they're an obvious choice each time your outfit needs ...

True Classic is stepping outside its usual staple-tee territory and into footwear with its first-ever collab: the True Classic x Timberland PRO Chelsea Boot. Designed in partnership with Timberland’s ...