CARRY-ON
Ortlieb Back-Roller Classic

Like to haul bigger loads, like a laptop, on a rear rack? Get ORTLIEB's grab-and-go BACK-ROLLER CLASSIC (pair, $165; ), one of the toughest, and best-looking, waterproof panniers available.
Check out 2009's best commuter bikes and our bike commuting bible.
Commuter Bike Bags: Acorn Boxy Rando Bag
Acorn Boxy Rando Bag

CARRY-ON
ACORN's canvas-and-leather BOXY RANDO BAG ($170; ), a classic randonneuring design, sits on a small front rack, is easily removed for carrying with an optional strap ($11), and will keep your stuff dry in all but the soppingest downpours.
Commuter Bike Bags: Ortlieb Packman Pro 2
Ortlieb Packman Pro 2

CARRY-ON
ORTLIEB's waterproof PACKMAN PRO 2 ($150; ) features a breezeway for your back, a helmet net, and cushy shoulder straps.