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Lucky Haul: Rag & Bone's Mini Pilot Bag

Buying, not browsing, is my go-to method for shoe, pants, bras and all other types of clothes shopping. I pretty much have a 99.99 percent success rate with picking items I wear to shreds—and that comes from not over-thinking things.

Handbags though, are the exception to my laissez-faire purchasing policy. When it comes to getting a new one, I research and agonize and research some more. I'll go into several stores, gather every style I like in a great big pile and pose with each one in front of the mirror. All of them get opened and stuffed with the contents of my current purse. "Oh, I'm just looking, thanks," I tell the salesperson like 10 times, even though I'm obviously doing more than that. Forty minutes later, I'll leave empty handed, internally in turmoil.

Part of it, perhaps, is the money. The bags I covet most waver just below the four digit range, some even bob dangerously above it—an investment not to be taken lightly. Yet there's plenty of footwear that costs that much, too, and it doesn't stress me out. Whenever I shell out an exorbitant amount of cash for new boots or oxfords I just tell myself how they're classics…that I'll wear them forever…and I can take them to Leather Spa—my favorite shoe repair spot in NYC—to get resoled year after year after year. What's more, satchels, clutches and totes date much faster than shoes. I always want to find one that isn't an "it-bag."

It was that nearly impossible-to-meet criteria that eliminated a Celine Luggage Tote (it's been the dominating accessory of every street style picture for the last two years; I'm scared it will start to look cliche the minute I buy one), a Proenza PS12 (same deal) and 3.1 Phillip Lim's Pashli Satchel (love 'em, but everyone has my office has a version) from my most recent carryall quest. However, after nearly three months of sweeping SoHo and Googling the same e-tailers so often that the search results noted "You've visited this page many times," I settled on the smaller version of Rag & Bone's Pilot Bag in mocha. It's dimensions are just roomy enough to fit everything I need for the day at work—I managed to squeeze my lunch, wallet and a paperback in there this morning. But it's still quite small, so I don't knock into everyone when I go out afterwards. There's a long crossbody strap so I can go hands free and useful outer pockets for easy access to my metro card and iPhone. As for its level of timelessness-yet-of-the-momentness? Hard to say. But I have received several compliments from people who had no idea what brand made it. Which is kind of best compliment of all.

Small Pilot in Mocha, $725, ragandbone.com