One True Thing: The Weekend Bag
The want: A weekend bag that isn't covered in logos yet doesn't reek of yacht club pretensions. It should sling over your shoulder, fit in an overhead, and look appropriate in the back seat of a convertible.
The Get: Billykirk's Large Carryall No. 166 ($340, billykirk.com). The sturdy canvas bag, available in black and olive, is small enough to take on the plane and large enough for a long weekend's needs. The leather bottom and hand-stitched tags and shoulder straps combat the elements while the metal frame ensures your clothes won't arrive crushed or crumpled.