Tumi Pax Patrol Packable Travel Puffer Jacket, $195 from tumi.com
Tumi's versatile water-resistant jacket packs a surprise: an inflatable travel pillow hidden in its collar. Its simple, minimal design lends itself to a wide range of social settings while its down insulation will keep you warm. Seen here in the mandarine color, it's also available in silver gray, navy blue, and black, from sizes small to XXL.