Shop Till You Drop! Gayle and Adam Go Outlet Shopping

Got a pulse? Well, then, chances are pretty good it'll race at the sight of a TAKE AN ADDITIONAL 50 PERCENT OFF sign. Everybody wants to walk out of a store feeling savvy and at least a little bit triumphant, and Gayle King, O's editor at large, is no exception. The woman appreciates a bargain. She is not above asking for the exact location of the slightly creepy guy who sold her friend a fabulous $30 faux-leather overnight bag from the trunk of his car. But more often than not, cheap-faux-leather-bag guy has moved on.

Enter O's creative director, Adam Glassman, a man who possesses a dazzling superpower: the unerring ability to know when 25 percent is being taken off anything, anytime, anyplace. "If it's a bargain you're looking for, we need to hit the outlets," he says. Gayle is skeptical. "I love a good deal, but at an outlet? I don't know, I usually end up wandering aimlessly. This whole Woodbury thing is a mystery to me," she says.

The "Woodbury thing" Gayle refers to is Woodbury Common Premium Outlets. Located about an hour north of New York City, the 150 acres of wall-to-wall discounts make Woodbury the largest collection of designer outlets (220 to be exact) in the United States. This is the place that separates the planet's true shopping geniuses from your basic Saturday-afternoon mall browsers. It's the place that draws more than ten million people a year from all over the world. It's the place costume designers come to dress women on the soaps, the place members of a certain royal family and at least one Jonas brother come to save a few dollars, the place that kicks off Black Friday by opening at midnight on Thanksgiving, and now it's the place Adam will take Gayle for a crash course in outlet shopping.

She suggests that they head up around lunchtime on Sunday. He suggests that she has some sort of death wish: "The weekends are insane. If we have to go on a Sunday, then we need to get there before the stores open. The key is to get a parking spot that's right near the entrance." He plots strategy much the way General Petraeus coordinates an air strike. "You see, if I go to the outlets in Palm Springs, I like to go midday, when it's way too hot to be on the golf course, but if I'm shopping the Orlando outlets, I go after dinner because they're open until 11. On the other hand, if—" Gayle cuts him off before he can get out his PowerPoint: "How's Tuesday for you?"

On Monday night, Adam all but color-codes a map of the stores he wants to check out (there will be no "aimless wandering" on his watch) and e-mails his preshopping marching orders:

1. Wear something that's easy to slip off and on.

2. Remove any nonessentials from your purse. If things go according to plan, we'll be carrying a lot of bags, so you want to travel as light as possible.

3. Get your makeup on and your hair looking good. You'll be logging a lot of mirror time, and the lighting in most dressing rooms is notoriously cruel. You don't want to find yourself trapped in a schlumpadinka moment.

4. Be sure to wear really comfortable shoes.

Gayle shows up Tuesday morning in a simple wrap dress. Her shoulder bag holds little more than a wallet. She has lipsticked. She has combed. The shoes are another matter. "Oh, Gayle," Adam moans at the sight of the floral clogs she has paired with lacy black peds.

"They were my only clean peds, and you told me 'comfortable,'" she says defiantly. "If I'm in the wrong shoe and I've got a lot of walking to do, I get these shooting pains that start at my toes and go straight up to my vagi—"

"Okay!" Adam announces before Gayle can finish the thought. "We're starting with Oscar!"

For those playing the home game, Oscar is fashion superstar Oscar de la Renta. His clothes are as common on the red carpet as Entertainment Tonight and borrowed diamonds, which is good news for Gayle, who has several big parties coming up. "I need a gown and a dress and a—" Adam calls for a time-out and offers his first insight of the day: "There's an old saying—'Outlet shoppers plan and God laughs.'" He explains that it's fine to have some sense of what you really need; otherwise you'll wind up with a bunch of "terrific buys" that never see the light of day. "But," he continues, "you can't come to a place like this with a concrete agenda, any more than a great chef can sit down and plan two weeks' worth of menus. He just has to work his way through the greenmarket to see what looks fresh that particular morning. He's gotta stay open to possibility."

Gayle hears what he's saying...sort of. She is, after all, a woman with a mission: She needs something to wear to a movie premiere and she's taking a no-retreat, no-surrender approach to finding it.

They enter the Oscar de la Renta store as if entering the Promised Land: Clouds part. Angels sing. Within minutes, Gayle is modeling a 50 percent off turquoise-and-tangerine halter dress for Adam. "Gayle," he says, studying her from every angle, "do you see how this is fitting in back? I mean, it's perfect if you want to work at a Howard Johnson's...or if you are a Howard Johnson's. I don't care if they're giving it away; this would be wrong for you at any price." As he helps with her zipper, a strappy red alligator pump catches his eye. It is love at first sight.

"My God, Gayle!" he says in a voice usually reserved for people who find a perfect likeness of the Madonna in their waffle batter. "These shoes were $3,600 and now they're 448 bucks," he says, kneeling down to slide them onto her feet. But he lost Gayle right after the word thousand; she hasn't heard a thing since. "They're not even comfortable," she mumbles. He repeats the new and vastly improved price. "Okay," she says, momentarily taken by their sleek silhouette, "maybe they're starting to feel a little more comfortable." Then, snapping out of it, she adds, "But I still wouldn't spend $448 on a pair of shoes." Adam points out that alligator is a classic, that they'll still be in style 25 years from now, that she'll get more use out of this one perfectly constructed, totally timeless pair at $448 than she'd get if she were to buy three trendy pairs for the same amount. Gayle studies the thin red strips crisscrossing her feet and finally replies, "Forgive me, but I might feel like these alligator shoes were more of a deal if they had a little more actual alligator on them. By the way, when is lunch?" Adam reminds her that this is only their first stop and hands her two cocktail dresses and an energy bar.

One of the dresses, a gray, blue, and sunflower-yellow print, has potential. "Wait a second!" Adam says, cinching a yellow patent leather belt around Gayle's waist. The belt does the trick; it nips her in and completes the look. She loves the dress. He loves the dress. Her accountant will love that the dress is half price. But there's a problem: "Whoa!" Gayle screeches, jumping back from the belt's $245 price tag. Adam points out that it's the perfect width, just the right color, and "she who hesitates is naked at a movie premiere," but the day is young and Gayle is convinced she can find a belt for much less money at one of the other shops.

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.

They move on to MaxMara, where Gayle tries another gala-worthy silk dress. "How do you like it?" she asks hopefully. Adam circles her twice, shrugs, and says, "Well, I suppose it's good for TV." Gayle knows this is Adam-speak for "You look more or less okay—from the waist up."

"It's a little clingy," he adds. "Let's go up a size or two." Gayle looks at him as though he's proposed that she remove her own spleen with a grapefruit spoon and flatly refuses. "The thing is," he continues diplomatically, "sometimes merchandise ends up at the outlet because it's sized incorrectly. This is definitely running small, but if you shop by what fits instead of the size on the label, you can find some amazing deals." He picks up a white sleeveless sheath splashed with an oversize teal-and-taupe floral print. "Here's a perfect example. This is gorgeous, but it's obviously not a true size 10. Somebody probably tried it, decided it was tight, and didn't go that extra step of giving the size 12—which is actually cut like a 10—a chance."

That shopper's loss is Gayle's gain. The flowery sheath retails for $745, was reduced to $447, then $312, and thanks to a tiny defect near the zipper, is on sale for $242 ("An almost invisible flaw can lead to a major steal," Adam says).

At Frette, Gayle points to a shelf of sheets under an 80 PERCENT OFF sign and exclaims, "Now, that's why I came here!" Adam agrees: "The quality of their cotton is remarkable, but there aren't many complete sets here at this kind of discount. The biggest deals are mostly on open stock, so this is a perfect place for filling in when you need some extra pillowcases or another top sheet." At Jimmy Choo, the incredibly kind staff provides bottles of water, loads of encouragement, and luscious lizard slingbacks for Gayle to consider. "If you're a militant fashionista, looking for the shoe du jour, an outlet might not be the place for you," says Adam, taking the shoes to the cash register. "These are from last season, but they're still incredible—they're 60 percent off and neutral enough to work with all your stuff."

At Roberto Cavalli, Gayle spots a beautiful butterscotch yellow belt and thinks she's hit the jackpot, but it turns out to be even more money than the one at Oscar. She looks at the shopping bags they've managed to amass and realizes that they've actually scored some great deals, but the De la Renta belt is beginning to haunt her.

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