Face it: there are precious few designers out there who have built a top-to-bottom lifestyle brand quite as well as Ralph Lauren. As a teenage high schooler in South Florida, I stocked up on the label's pony-embroidered polos in every available hue. Nowadays, just walking past the windows of Ralph's Bleecker Street boutique makes me want to escape to a Montana cattle ranch and drape myself in fringed suede jackets and bolo ties. And with the introduction of lower-priced line Denim & Supply, the iconic sportswear company has once again proven its mastery of Americana chic—though this time around, the look's more warehouse-weathered than Wild West. We're particularly smitten with the Corduroy Snorkel Jacket ($250), Jacquard Boyfriend Shirt ($145), and Nylon Down Toggle Vest, all of which would make for prime layering pieces once winter weather sets in—but click on over to the Denim & Supply Ralph Lauren website to shop the collection yourself!