The investment: $698
Why it's worth it: Don't let the fact that you'll find this perfect, will-only-get-better-with-wear leather weekender in Coach's men's section bother you; you can find some pretty amazing stuff there (try the boys' department at J.Crew, for example, or that cashmere pullover you borrowed from your boyfriend and aren't giving back). The fact is that this weekender isn't just gender neutral, it's a classic. It's the kind of luggage that looks like you inherited it from a grandparent with its timeless, unassuming shape and luxe finish. Since we weren't so lucky, it's also the kind of piece we wouldn't mind investing in on our own — a piece that will give us that sophisticated, world-traveler look, no matter where we're headed. Plus, years from now, we will be the grandparent that gifts our granddaughter (or grandson) with this perfect travel companion — one that we suspect will look just as gorgeous then as it does now.