You can’t argue with the perfect marriage of form and function that has kept these iconic boots in heavy rotation ever since they were introduced decades ago. The fashion focused will tell you these brands are in vogue again. We say these winter-ready boots will forever keep their cool.

Heavy Hitter, $270
Green Kangatan 8180s from Red Wing Heritage are a sharp update of a design issued in partnership with Red Sox Hall of Famer Ted Williams back in 1963.

Doc This Way, $200
Dr. Martens (a.k.a. Docs) of every style and color are ubiquitous again, but you can’t beat the reissue of the vintage oxblood eight-eyelet boots for classic cool.

Timber!, $155
Timberland’s original yellow boot remains the quintessential footwear that bridges manual labor and manly street style.