Gayle and Adam
Photo: Jonny Valiant
Gayle King never met a piece of clothing she didn't want to hang on to. Adam Glassman never met a mess he didn't want to tame. Lisa Kogan reports on the makeover that nearly killed them both.
It began as virtually every Adam and Gayle adventure begins: Gayle lamenting that she can never find what she wants to wear when she wants to wear it, Adam, who lives to create beauty from chaos, immediately offering to stage a closet intervention, Gayle politely declining, Adam sweetly insisting, Gayle mumbling something about not wanting to be pressured into getting rid of the things she loves, Adam explaining that he'd merely be removing the things that clutter up her life, Gayle folding her arms across her chest and staring at the floor, Adam sighing heavily and fishing through his pockets for an Excedrin. But in the end, Adam was able to use his gentle powers of persuasion to quell Gayle's concerns and charm her into submission, or as Gayle puts it, "He kept browbeating me until I just couldn't take it anymore."

Which is how it comes to pass that early on a Tuesday morning, Adam arrives at Gayle's front door along with O's assistant fashion editor, Kristina Lepore, and the extremely patient and incredibly talented Jeffrey Phillip, head of the New York organizing and design firm that bears his name. They study the hodgepodge of dresses, the heaps of sweaters, the tangle of scarves and belts, and the clutches, totes, and handbags occupying nearly every square inch of floor space. "The problem," Adam concludes, stepping over a mound of high heels, "is mass more than mess."

Adam's diagnosis comes as no surprise to Gayle, but what's a woman who cohosts CBS This Morning five days a week, while also working full-time as editor at large of this magazine, to do? She tries to explain that holding down two high-profile jobs requires a major wardrobe. She points out that styles change and weight yo-yos. She's even willing to acknowledge that certain items were wrong from the get-go. But perhaps the biggest reason her closet runneth over is that many of these pieces hold memories ("I was a 'mom model' at my son's school in that outfit! I wore this dress to the White House!") that feel too important to simply toss. "Gayle," Adam begins, "memories may be beautiful, and yet...." It's not quite 9 A.M. and he is already reaching for a Streisand lyric. He tries again: "Listen, if you like something and you use it often, you should definitely hang on to it. But you have to keep your eye on the prize. Our goal is for you to have instant access to the stuff you still need, love, and actually reach for on a regular Basis." Unfortunately, the only way to determine what those things are is to examine every single item.

Jeffrey sets up four areas outside the closet: give to family/friends, needs repair/reconfiguration, donate to charity, and do not remove under penalty of death.

They kick things off with a no-brainer: Gayle pulls out a terrific leopard wrap dress. "I read in O magazine that animal prints are very in." Adam nods his approval and the dress goes straight to the do-not-remove section. "I bought this because I know I'll lose weight," Gayle says, holding up a cherry red sheath with just a hint of defiance. "But Gayle," Adam counters, "why buy clothes that don't fit?" He suggests she ship the sheath to her daughter, Kirby. "I mean it's very old lady, which is kind of chic on a 25-year-old who wants to look more sophisticated, but on a woman who—" Gayle shoots him a look that's chilly enough to store fur in, but concedes the point. He pulls out a two-piece print. "This has definitely seen better days. It's pilling, it's stained, it's out." Agreed. Next comes a futuristic little number in black and cream. "So, Gayle," Adam asks, "are we auditioning for Star Trek?" She describes running into a friend, "and this thing looked so fantastic on her that I went right out and bought it for myself." Adam understands the urge to buy something we've loved on a friend. "But," he says, "your shape, your hair—you're working a very different vibe from your pal Lieutenant Uhura. You've got to stay true to your own style."

As the morning progresses, Gayle tries repeatedly to justify her purchases. Phrases like "It was in the window and I was in a hurry" and "It was a charity event, so I had to buy something" come up several times. She also tries to build a case for keeping her stuff: "Macramé used to be very cool!" she says, brandishing a pale peach cocktail dress covered in lacy little knots. "So was cigarette smoking," Adam answers, pulling the dress out of her hands and passing it to Gayle's assistant, Arianna, who passes it to Kristina, who passes it to Jeffrey, who rushes it out the door. "Oh, I love this dress! Oprah gave it to me in 1984," Gayle says, holding up a marigold and black Ungaro with the kind of shoulder pads seldom seen outside the Pittsburgh Steelers defensive line. Adam looks at the dress, then at Arianna, and decides it's time for a new rule: "Generally speaking, Gayle, your dress should not be three years older than your assistant." He adds it to the charity pile before she knows what hit her.
Gayle and Adam
Photo: Jonny Valiant
Some lucky pieces do get a reprieve: A slightly dowdy jersey can be updated by removing the sleeves and scooping the neckline, pills can be shaved off a cashmere sweater. A gown can be refashioned into a sleek party dress. A fabulous brooch is salvaged from a little black Carmen Marc Valvo that's way too short. More often, though, the verdict is thumbs-down. A midnight blue metallic wrap dress Gayle got back in the '90s is now deemed "dated"; same for a fitted tweed jacket, and it is decided that a pair of khaki shorts Gayle calls her "Out of Africa look" should be returned to Africa—pronto!

A poufy Cinderella confection, complete with tulle skirt and satiny bodice, still fits just fine. "But it's trying too hard, Gayle," Adam explains. "You are chicer than this gown. You've moved on." Gayle tries on a floor-length milk-chocolaty brown A-line that laces up the sides. Adam stares. "You don't think this is great?" Gayle asks. "I wore it to Alicia Keys's Egyptian party." She twirls her way to the mirror. Adam circles, looks her up and down, and finally responds, "You appear to be waitressing at some sort of medieval-themed restaurant. I keep waiting for you to serve me a giant drumstick and a goblet of mead." Gayle looks to Jeffrey, who averts his eyes. She models for Kristina, who busies herself near the belts. "I love this dress," Gayle pleads. "My entire mission in life is to get rid of this dress," says Adam, refusing to budge. There is only one thing to do: Break for pizza.

After lunch everybody takes a deep breath and braces for the big bag clearance. Adam holds up a lovely malachite green Kate Spade with a large spot near the strap. "Is that bird poop?" he asks. "White hot chocolate from the airport Starbucks," Gayle answers, dropping it in the repair pile. Adam holds up four of the same tote, each in a different color, each in pristine condition. Gayle explains that they were a great deal and she got them "for bopping around." Adam tells her that they're only a great deal if you really use them. He then picks up a small evening bag that appears to be made of faux muppet. Gayle starts to laugh. "I was at a dinner party and I put this purse down near my feet and a very nice woman came over and said, 'Oh, what a darling little dog—and he's so well behaved!'" Bye-bye doggie bag. Still laughing, Gayle reaches for a handful of dried cranberries sitting on the counter as Adam asks her to focus on the better stuff. "I'd rather see you with a few quality bags than a lot of cheap ones. Out with the mock croc, in with the timeless classics." But Gayle is only half listening. "Where did we get dried cranberries?" she asks, popping two more into her mouth. "Um, Gayle," Jeffrey says quietly, "we found those in one of the bags, and we don't know how old they are. Actually," he pauses, "we don't even know that they're cranberries."

Shoes are the next Everest waiting to be scaled. In Gayle's life, clogs are a must; ditto flip-flops and slippers. Fair enough, but Adam pronounces a pair of hot pink, pointy-toed slingbacks "perfect for killing roaches in tight corners." Next Gayle slips into a Pucci pump that Adam vetoes on the grounds that it's even pointier. "Won't they ever make a comeback?" Gayle asks. "Yes," Adam says, "but the heel will have changed or something else will be altered enough that you can let these find a new place to live." Little green shoes with brown ribbon trim are cool, comfortable, and a gift from Diane Sawyer—they stay. Supersexy rhinestone stilettos that are impossible to walk in for more than six seconds at a time will be donated to the first fabulous masochist the team comes across. Charcoal gray is hard to find, so mules in that shade make the cut. After much debate, a lot of the shoes go to charity, a lot go to repair, but the vast majority stay put.

Day has turned to night. The leftover pizza has been reheated for the last time, Dancing with the Stars is winding down, and Adam opts for picking up the pace. Because Gayle doesn't own as many slacks and blouses as she does dresses, and because her resistance is starting to flag, and because she is craving a little time off for good behavior, pants and shirts are tackled with relative ease. Sweats for long plane rides and days with a head cold: keep. All but a couple of baseball caps: toss. Jeans that are a bit tight can stay. Jeans that can't be pulled past the thighs can go, and it is made very clear that "in 2012 friends don't let friends wear jeggings."

Ultimately, 152 dresses, 77 sweaters, 17 skirts, 13 coats, 12 pairs of jeans, two pairs of pants, 13 belts, 62 pairs of shoes, and 67 bags will be finding their way to other people's closets. Jeffrey and Kristina begin pulling the bags earmarked for charity out the door before Gayle can start second-guessing herself, as Adam takes a deep breath and surveys the open spaces. "You did a really good job today. You let go of more than I thought you'd ever be willing to part with," he says, exhausted but happy.
"Sometimes you just have to have somebody there to pull the trigger, and you, Adam Glassman, are a mighty good gunslinger," Gayle says with a soft sigh. She is a little bit anxious, a little bit relieved, and a lot in need of a cupcake.

But Adam has something even sweeter to offer. He leads her to the dresser and opens the bottom drawer. Gayle stares deep into this drawer that once brimmed with necklaces, socks, scarves, and the occasional half slip, a drawer she'd dig through again and again before giving up on the pieces she knew were there but could never quite put her hands on, a drawer that drove her absolutely nuts. She is stunned. "I can't get over this," she says. "I used to think I didn't have enough drawers, and now I actually have an empty one!" Adam pats his friend's shoulder. "Gayle," he says, "I'm pretty confident that one of these days, you'll find a way to fill it."

Two weeks later, Jeffrey Phillip, organizational genius, and Adam Glassman, force of nature, have whipped Gayle's world into shape. "We didn't create the closet I'd want for myself, because what makes sense for my life wouldn't suit Gayle," Adam says, pointing to a rod full of hangers draped with sweaters. "For example, I never hang my knits because they lose their shape, but Gayle has to be out the door by 4:30 every morning, so she's not about to start hunting through drawers, unfolding and refolding her stuff. She needs a system that allows her to grab and go. And God knows, this is a woman who loves to shop. So now that we've de-cluttered, we've applied the same organizing principles that are used in a boutique. We've displayed things in ways that make sense.

"For starters," Adam says, "I've invested in some cheap and cheery linen boxes: one for opaque tights, one for sheer stockings, one for control-top Spanx, and one for leggings." Each box is labeled clearly because "you want to know where things are in an instant."

He points to the workout wear sitting on wire risers. "Jeffrey discovered these in the kitchen section of the Container Store. They're usually used in cabinets to create extra room for canned goods, but they're great for Gayle's Pilates stuff." Picking up a Joy Mangano Huggable Hanger, he demonstrates how a thin, well-made hanger can free up roughly 25 percent more space in your closet.

"Gayle responds to color," Adam says, "so we color-coordinated her clothes in different sections of the closet." Reds, oranges, corals, pinks, yellows, greens, blues, violets, and blacks each hang as a group, with prints going to the group with the dominant shade. On the shelf directly above each section of dresses are the bags that work with its particular hue. Jeffrey uses bookends to keep clutch bags upright in a neat row. He also stuffs Gayle's handbags with shoe bags that have been filled with crumpled newspaper. "The stuffed shoe bags help totes and hobos maintain their shape." Adam says. "And when you're on the run, you don't leave balls of newspaper all over the floor. Everything stays contained."

Gayle's dresser, which is a large drawer-filled island that floats in the middle of the closet, is generally for underwear, but within this plan there are subcategories: camis, shapewear, bras (each folded neatly in half), and T-shirts (rolled, rather than folded, so the design is easily visible), which are again divided—short-sleeved graphic tees, long-sleeved crewneck tees, and long-sleeved V-neck tees.

Jeffrey removed a bar where Gayle's jeans were doubled over hangers in two rows. They now hang from the waist, organized by size to accommodate any weight fluctuations that might occur due to, oh, let's say, the stress of sorting through every item you've ever worn.

Expandable plastic cosmetic trays are placed in drawers to hold Gayle's jewelry. Jeffrey has divided her pieces into gold tones and silver tones, then organized the remaining pieces by predominant color. He keeps rings with rings and bracelets with bracelets.

Measuring the height of the highest shoe in the shoe closet at nine and a quarter inches, Jeffrey then moved the shelves up to gain more space at the bottom of the closet, where he was able to bring in additional shelving and give a lot of extra shoes a place to live.

"Okay, Gayle; I think you're all set," Adam says as he takes one final look around. "The key to this is maintenance. Now that we've created a space for everything, you've got to carve time out of your schedule—it could be five minutes each night, it could be 25 minutes every Saturday morning, whatever works for you—to make sure everything is back in that space. Otherwise things will snowball and I will be forced to move in with you." And for a split second, they both look terrified.

Keep Reading: Go behind the scenes of Gayle's closet makeover

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