Adam Glassman and Gayle at Elie Tahari
At Elie Tahari, Gayle tries on a jersey dress.
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Next stop: Tory Burch. Adam leads Gayle to the outer edge of the store. "Managers know that it's human nature to automatically walk straight to the heart of a place, so things are pricier in that area," he says. "This is why I always scout the perimeters first, especially the very back, because that's where the higher markdowns are. Then I scope out the middle section, and I finish with the accessories." Sure enough, along the back wall, Gayle finds a shift with a cool vintage quality that would suit her daughter perfectly. "This could be so pretty on Kirby, but I'm not sure it will fit her," she says. Adam explains that a shopper should always check a store's return policy, as they can vary dramatically: "If you're just not sure, then go for the bigger size. It's a lot easier finding a good tailor to take the dress in than a good surgeon to liposuction the fat out."

The good news is that in this case, Gayle has a week to make an exchange and the store has quite a few other sizes in stock. But now Gayle is wondering why there are so many pieces of this particular style. "Well, it could be that it just didn't sell," says Adam, "or a store cancels an order, or a shipment will arrive late and they miss their retail window. The surplus lands at the outlet—in this case marked from $385 to $231."

As Gayle hands over her credit card, a common shopping scenario is unfolding. "Look over there," Adam whispers. "That woman is making a rookie mistake." The only thing Gayle sees is a half-dozen women trying on clothes. "Do you notice how they're talking their pal into that blue tunic top? It's really pretty, but she keeps staring at the price tag; it's making her nervous." Gayle takes his point. "It may be 75 percent off, but if you truly can't afford it, then it's not a good deal," she says, hoping to send subliminal support toward the frazzled woman in the tunic. "Exactly," he says. "I'm all for going shopping with one trusted buddy, but groups of people should split up and meet at the end of the day."

They manage to find two fantastic things at the Elie Tahari store: (1) An ultrachic wool coat with a portrait collar and princess seams that's marked down to a third of its original price, and (2) Shaunté, the clerk who keeps running back and forth, bringing anything she thinks might work for Gayle.

Husbands come and go, lovers are a dime a dozen, children eventually grow up, but in the world according to Adam, the bond between salesperson and client is sacred. "Take a second to see if one of the sales team really stands out, and then ask her to work with you. Someone like Shaunté can call you when a new collection is coming in, let you know when the piece you adored gets marked down again, send you an extra coupon, even check other outlets for your size," he says, gathering up shopping bags. "And if you make a major purchase, she'll probably be willing to ship it to your home." As Shaunté puts the coat in a garment bag, Adam notes, "Shopping off-season saves a ton of money. The trick is to avoid the trendy stuff that will look dated after a few months."

Standing by a couple of pigeons picking at a bun, Generalissimo Glassman consults the map that is his lifeline, as Gayle gazes longingly in the direction of a Nathan's hot dog stand. "Just because I refuse to spend $245 for a belt doesn't mean I wouldn't pay that for a hot dog right now," she says. But lunch is not an option. "It'll only slow us down," Adam says, pulling her to their next destination.

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