Barbour x Rockport, $210
(available at Macy's in November)
Why have one, when you can have two? This fall, there's a handful of leather boots with cotton and canvas inserts on the uppers. From Red Wing's beloved hand-sewn Wabasha boots to Sebago's kettle boot sewn with Filson's tin cloth canvas and Rockport's cap-toe style trimmed in Barbour's signature waxed cotton and plaid lining. The resulting boots are lightweight yet rugged. Ideal for an autumn weekend—no matter the weather.
Sperry Top-Sider, $120