Hugo Boss Porthole Messenger, Handbag of the Day
Men don't usually carry handbags, but a messenger bag can offer all the benefits of a purse while sparing the carrier some raised eyebrows. The Hugo Boss Porthole Messenger is a sleek leather bag with a canvas trim and aged brass hardware. It measures 15.5" x 12" x 4", so it is large enough to fit books, folders and even a small laptop, though the fabric-lined bag isn't padded enough for it to replace a real laptop case. It has a front flap, which secures with two buckles and conceals a small front pocket. The wide canvas and shoulder strap is easy on the shoulders and adjustable in length, so the bag can be carried under one arm or worn across the body. Price: $450.