22. The Extra-Large Tote — When you're not quite in need of a duffle or weekender, but can't fit all your stuff in a backpack, you'll start recognizing the beauty of these oversized totes. They hold a seemingly endless supply of all the crap you need for a couple days away, plus, for some reason, they never really feel that heavy. We suggest buying one with a zip so you're boxers don't end up flying out on a bumpy Jitney ride.

Barbour + Jack Spade Waxed Canvas Tote, $350, available at Barneys; L.L Bean Hunter's Tote Extra-Large Bag Zip-Top, $39, available at L.L. Bean.