1. Andrea Wishom, Senior Supervising Producer, 42
"I've made a lot of memories in my 17 years here," says Wishom, who helped create episodes ranging from the September 11 tribute to this season's Australian extravaganza. "But I can already say with certainty that the most important two hours I'll ever produce are still to come." She's referring to the surprise show that's scheduled to air leading up to the May 25 finale. "It's our farewell to Oprah, and she has no idea what we've got in store!" A tiered silk dress (Marc by Marc Jacobs, $528) is a romantic departure from Wishom's "simple, conservative" everyday wear: "Honestly, I don't like a lot of attention, but this is a showstopper."
The Wardrobe: "We swapped Andrea's conservative, neutral dress for a soft cut and rich, saturated color."—Adam Glassman, O creative director
The Hair: "Cutting layers in Andrea's hair updated her style without taking away length."—Ken Paves, celebrity hairstylist and frequent makeover magician on The Oprah Winfrey Show
The Makeup: "A luminizing foundation adds polish but still looks natural."—Jeannia Robinette, Los Angeles–based makeup artist
Bandeau, American Apparel, $18. Earrings, Deanna Hamro. Bangles, Anna Sheffield and Ippolita. Shoes, Kate Spade New York.
2. Tara Denise, Production Designer/Lighting Director, 45
Denise has spent 19 seasons constructing and lighting elaborate sets for The Oprah Winfrey Show stage. "I've gotten to do so many really big, exciting things. In 2008 I arranged for us to have a 22,000-gallon tank of water for David Blaine to hold his breath in for 17 minutes—right after taping a "Favorite Things" episode. My team and I love when we can make the biggest impact possible and then take it away without a trace." Given the nature of Denise's job, "dresses would not be my first choice most days." But for a special occasion—say, a wrap party?—this plunge-neck silk crepe gown (AllDressedUp, $930) is magic
The Wardrobe: "A halter enhances Tara's chest and toned arms. And if you want to stand out, this is your color." —Adam Glassman
The Hair: "Texture, volume, and movement all add oomph to short hair."—Ken Paves
The Makeup: "Just a touch of bronzer on Tara's cheeks gives the most natural, sun-kissed look."—Jeannia Robinette
Earrings, Meus Designs. Bracelet, Maya Brenner. Ring, H.Stern. Shoes, Stuart Weitzman.
3. Jill Van Lokeren, Senior Supervising Producer, 43
"As we wind down, I don't feel sadness—only pride that I was a part of something so incredible for 15 years," says Van Lokeren, who has overseen all things production, from scriptwriting to the final cut. "In 2003 I went with Oprah to the Pontiac Correctional Center's death row. I'd had images in my head of monsters clanking their tin cups against the bars, but speaking with those men was the most humanizing experience of my life." Comfort has always been key for long days behind the desk; the embroidered cardigan (L'Wren Scott) and satin pencil skirt (By Malene Birger, $265) are not only easy to wear but fit Van Lokeren's "classic meets retro" style.
The Wardrobe: "A cardigan and pencil skirt flatter every figure. This particular pairing proves that redheads can wear red."—Adam Glassman
The Hair: "We gave Jill big waves by drying her hair with a diffuser and then using a large-barrel curling iron."—Ken Paves
The Makeup: "Shaped, filled-in eyebrows frame the face the way nothing else can."—Jeannia Robinette
Bracelet, Suzanne Felsen. Ring, Phillips Frankel.
4. Jakki Taylor Richardson, Senior Associate Producer/Booking, 39
"One of the first shows I worked on was Oprah's 50th birthday, when Gayle King and John Travolta surprised her with a party," says Taylor Richardson. "Every part of the production was huge. I remember being up in an edit bay at 2 A.M. before running across the street to check on the 400-pound cake and thinking, 'Wow. I've really stepped into something big here'." Taylor Richardson recently added "new mom" to her job description; as a result, she says, "I'm less of a fashion risk-taker than I once was." A gold-and-black sequined dress (Michael Michael Kors, $130) topped with a suede-trimmed trench (St. John, $1,295) is a sure thing. "This outfit says, 'Watch out, here I come.'"
The Wardrobe: "A khaki trench is transformative. It works over jeans or a sparkly dress—in that case, just keep accessories to a minimum."—Adam Glassman
The Hair: "We gave Jakki extensions to prove that a medium-length style can be just as easy to care for as a short one."—Ken Paves
The Makeup: "Shimmery copper and bronze eyeshadows are gorgeous on dark skin."—Jeannia Robinette
Bracelet, R.J. Graziano. Ring, Sheila Fajl. Shoes, Claudia Ciuti.
5. Sally Lou Loveman, Senior Audience Producer, 49
Loveman has been in charge of studio audiences—40,000 guests per season—since 2003. "When you work here, exciting things happen all the time," she says. "That's the Oprah drug. But I've definitely had a few bloopers. Once, when Kenny Rogers was on, I finished the audience warm-up by shouting, 'Kenny Loggins is here!' Another time, I invited people onstage to dance before the show, and one guy went into a disco move and accidentally smacked me in the face. That was a big, beefy hand. I was seeing stars." With a job requiring so much running around ("I sweat a lot"), Loveman has long been a fan of all-concealing black. This draped jersey gown (David Meister, $578) is an effortless way to try a new shade. "Now I want an invitation to go somewhere!"
The Wardrobe: "By putting Sally Lou in a monochromatic column dress, we made her appear taller."—Adam Glassman
The Hair: "Heavy bangs, cut from the middle of the crown, look very rock 'n' roll."—Ken Paves
The Makeup: "Sally Lou's smoky eyes look superdramatic with lots of charcoal eyeshadow and black mascara."—Jeannia Robinette
Earrings, Badgley Mischka. Cuff, Madyha Farooqui. Bracelets, M.C.L. by Matthew Campbell Laurenza.
6. Cindy Mori, Director of Booking and Talent Relations, 43
As leader of the staff that booked the show's guests, Mori has had her share of challenges, including the annual star-studded "After-Oscar Party." "Those shows often came together at 3 or 4 in the morning, because we never knew ahead of time who would win. In 2009, when Sean Penn got Best Actor, I snagged him as he was walking off the stage—'Will you join us tomorrow to celebrate on the Oprah show?' I have a photo in my office of me accosting him that night." Mori would wear this metallic dress (Basix Black Label, $550) to a party "in a heartbeat. I still feel like myself, but my best self
The Wardrobe: "For a petite woman like Cindy, it's all about sticking to a solid color, then having fun with details—like a low-cut back and major heels."—Adam Glassman
The Hair: "With naturally curly hair, a perfectly proportioned cut is key."—Ken Paves
The Makeup: "The quickest way to add drama to a look? Matte red lipstick."—Jeannia Robinette
Earrings, Badgley Mischka. Ring, David Yurman. Shoes, Christian Louboutin.
7. Candi Carter, Senior Producer, 42
Carter has supervised a team of producers on both live and taped episodes. "My favorite shoot of all time was Oprah and Jay-Z in Brooklyn, when they visited his old neighborhood. We sat in the basement of his grandmother's former house, on lawn chairs—just Jay, Oprah, Gayle, me, an assistant, and two camera guys—and though it was hot as the dickens in there, it was so intimate. Oprah spoke to him for two hours, and I could see out the window as a crowd gathered. When we left, the whole street was filled with people." Carter calls herself "no-fuss" and confesses to occasionally coming to work in sweats. But this stretch-satin one-shoulder dress (David Meister, $470) "brings out my inner diva. When you put on something like this, you strut."
"This one-shouldered dress is current and
comfortable. Gathered fabric skims over Candi's midriff, an area she'd dressed to conceal."—Adam Glassman
"Switching to a richer haircolor brought out flattering tones in Candi's skin."—Ken Paves
"A few false eyelashes on the outer corners of her lids equal instant glamour."—Jeannia Robinette
Earrings, Badgley Mischka. Ring, Nicky Hilton. Shoes, Kors Michael Kors.
Go behind the scenes of the shoot with Oprah's personal phographer