The North Face

Although it was designed primarily as a high-performance mountaineering piece, The North Face Verto Jacket is a bike commuter's best friend. It packs down to the size of a baseball when you dont need it, and deploys into a wind- and light rain-blocking jacket when you do. It comes in the orange color seen here (great for hunting season!) and is also available in so-called sublime green, or a Hefty trash-bag black. The jacket is made from comically lightweight but seriously strong seven-denier fabric, comes in sizes S through XXL and provides a snug, weatherproof fit with elastic hem, cuffs and over-sized, helmet-friendly hood. At $130, its pricey, but in the right conditions, it's priceless.
$130; thenorthface.com
—Chris Lesser