Don’t be afraid to take your grandpa’s advice when it comes to leather. The flight jacket has been around for years, and it stays put because the look never goes out of style. It covers the entire range between the tire-kicking, war-time, aviator-adorned hardass and the driving-loafer-clad New England leaf-peeping communities, comes in several different formats (lined, unlined, weathered) and if you fall totally in love, seek out the companion luggage sets that are on the vintage market. [$400; llbean.com]
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