Gayle King and Adam Glassman at Prada
Gayle and Adam are the last customers of the day at Prada.
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Adam is philosophical. "You know, Gayle, I think where a lot of people go wrong is—well, it's a little like trying to pitch a tent in the wind. Just as you get one pole secured, a giant gust comes along and pulls the other pole right out of the ground, and suddenly you're back to square one. Now, you've bought this great dress," he says, motioning to the De la Renta bag. "But you don't have the belt, and the belt really elevated that dress. It turned it into something you felt gorgeous in. At an outlet, if you love it and have a purpose for it and can afford it, you should buy it! Otherwise, you call the store a couple of days later, and you've blown it. The belt is gone with the wind, and that dress never really gets worn."

Gayle thinks all this over on the way to Michael Kors. The store carries mostly Michael Michael Kors, his lower-priced line. "It's excellent," says Adam. "But let me show you where I'd say today's most impressive bargains are." He ushers her to a table of very cool bags. "Some of these are created strictly for the outlets—and include some of their best-sellers of past seasons at a lower price." Gayle picks out a canvas tote for herself ($165) and a woven metallic bag for Kirby ($202).

After nearly nine hours of solid shopping, Gayle and Adam have hit a wall. "I'm starting to lose my pleasing personality," Gayle says, ominously enough that, at long last, Adam springs for a soggy sandwich and a bag of chips at Au Bon Pain, and they find an empty bench.

Not even her beloved clogs have saved Gayle's feet from aching, and it's safe to say that Adam does not have a bright future as a sherpa—his shoulders are slumping, his back is shot. There is only one word that can get them up and moving again. Adam murmurs it quietly at first, then louder, stronger, evangelically: "Prada!"

It is dark outside, and the stores are getting ready to close for the night, but a few brave shoppers are forging on. They study the exquisite men's suits in the windows, they sample lotions and perfumes, and one of them removes her black lacy peds, takes hold of Adam's sore arm for a little extra support, and slips her feet into a pair of Prada pumps that could work beautifully with the De la Renta dress. "I bet I know what you're thinking," Gayle says. "If I invest in that belt, then I end the day with a lot of good deals and one solid head-to-toe look that I actually need. It would be a smart buy." Adam smiles and says, "By George, I think she's got it!" They make their way back to Oscar just before closing time.

Sneak a peek at everything Gayle actually scored

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