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.