I'm looking to invest in a designer handbag that I'll carry for years. Suggestions?
—Janet Richardson, Bellevue, Wash.

I turned to handbag designer Rafe Totengco for advice on this one. "I would invest in a bag in a great color, like bordeaux," he tells me. Translation: wine-colored. Somewhere between red and brown—in a good way. "It goes with everything, trust me." Bordeaux has another advantage, too: "It pops all-black outfits, and enhances color or prints."

What else to consider? Well, as much as you may love the clean, high-Italian style of that Valextra hobo—and, really, who doesn't?—you have function to consider. First and foremost, a bag is supposed to be a bag, and if it isn't, it isn't worth your money.

"Look for outside pockets and inside compartments for all your PDAs and other accoutrements," Totengco advises. Once you find that, "I would choose something you love, because if you start with this premise, you can't go wrong. I've had girls tell me they've worn certain bags of mine for years because they 'love' the bag. Doesn't purchasing a handbag begin with love at first sight anyway?"

Given the look of this Rafe handbag, it sure does.

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