Oprah on the cover of the May 2015 issue of O Magazine

Photo: Ruven Afanador

They are sewing up my dress so you don't see my bra-ssiere," said Oprah, holding still so tailor Nile Cmylo could stitch the back of her elegant Xscape gown. "And Lord knows I have to wear a bra-ssiere. Bra is not a bad word, people!" Foundation laid, Oprah channeled her inner Elizabeth Taylor to vamp it up old Hollywood–style...until a new problem breezed in. "The wind machine is making my eyes tear," she said, before urging the crew to pick up the pace: "Let's shoot this thing!"
Jenny Capitain, Nyle Cmylo, Oprah and Andre Walker

Photo: Sioux Nesi

Dream Team
Fashion editor Jenny Capitain, Cmylo (stitching Oprah's dress) and hairstylist Andre Walker.
Manicurist Roseann Singleton, makeup artist Derrick Rutledge and Oprah

Photo: Sioux Nesi

Nailed It
Manicurist Roseann Singleton and makeup artist Derrick Rutledge prep Oprah for the shoot.
Colored earrings

Photo: Sioux Nesi

Ear Candy
Amid a sea of colored earrings...
Leviev diamond earrings

Photo: Sioux Nesi

...classic white diamonds from Leviev were the stars.
Adam glassman picks out a chain necklace

Photo: Sioux Nesi

Chain Reaction
O creative director Adam Glassman peruses necklace options.
Oprah getting her brow makeup done

Photo: Sioux Nesi

Brow Beat
Rutledge plays up Oprah's brows. (To try this look, use Lancôme Sourcils Tint Eyebrow Pen, $26; Sephora.com.)
Long-sleeved dress options for Oprah's cover shoot

Photo: Sioux Nesi

C'est Chic
The elegant long-sleeved dress contenders.
Sparkle plenty

Photo: Sioux Nesi

Sparkle Plenty
Cmylo amps up the wattage of Oprah's on-trend navy gown by adding Swarovski crystals.
Behind the scenes of Oprah's May 2015 cover shoot

Photo: Ruven Afanador

Screen Gem
"It's very iconic," said Oprah of the first-ever black-and-white O magazine cover.
Andre Walker works on Oprah's hair

Photo: Sioux Nesi

Blown Away
Walker perfects Oprah's hair while photographer Ruven Afanador gets his shots.