Oprah behind the scenes

Photo: Sioux Nesi

Lounge Act


Cut to the Chaise: Oprah and her cabana boys—set designer Todd Wiggins and his team.

Since the most visible part of her face would be her cherry red lips, our cover model offered very specific direction on the shade: "I don't like a solid red," said Oprah. "You need to layer your reds so there's more of a tone-on-tone effect." She had less complicated feelings about her bright Satya Twena topper. "I do love a good hat," she said as she faux-sipped her prop cocktail. Quipped Gayle King: "You once wanted to do a hat issue every year, remember?"

On Oprah: Top, Caroline Constas, $395; ShopBop.com. Pants, Lafayette 148 New York, $298; Lafayette148NY.com for similar styles. Hat, $275; SatyaTwena.com. Earrings, Vhernier, $9,650; Miami, 786-615-2722. Ring, $7,500; JillHellerJewelry.com. Bracelet, Faraone Mennella, $31,000; New York City, 212-752-5884.
vintage cover

Photo: René Gruau/gruaucollection.com/Bridgeman Images

Ports Illustrated

Oprah's look was inspired by this 1950s ad from influential fashion illustrator René Gruau.
Wind-blown hat

Photo: Sioux Nesi

Second Wind
Tailor Nile Cmylo arranges the ribbons to look windblown.
chanel beachy shoes

Photo: Richard Majchrzak/Studio D

Beachy Keen

French Riviera-style stripes and luxurious whites are two classic summer trends.

Espadrilles: Chanel, $675 to $750; 800-550-0005
Alison Lou Necklace

Photo: Richard Majchrzak/Studio D

Necklace
Cropped Sonia Rykiel pants

Photo: Richard Majchrzak/Studio D

Cropped Pants

Sonia Rykiel, $670; Net-A-Porter.com
striped yellow shirt

Photo: Richard Majchrzak/Studio D

Shirt

Lafayette 148 New York, $248; Lafayette148NY.com
Striped beach hat

Photo: Richard Majchrzak/Studio D

Hat
White watch

Photo: Richard Majchrzak/Studio D

Watch

Bulova, $299; Macys.com
white tan bag tote

Photo: Richard Majchrzak/Studio D

Tote
red white striped one-piece bathing suit

Photo: Richard Majchrzak/Studio D

Swimsuit

Solid & Striped, $158; SolidandStriped.com
multi-color ring stack

Photo: Richard Majchrzak/Studio D

Ring Stack
striped blazer

Photo: Richard Majchrzak/Studio D

Blazer

$149; Zara.com
Makeup vintage

Photo: Richard Majchrzak/Studio D

Makeup
makeup bag Tilbury

Photo: Richard Majchrzak/Studio D

Makeup Bag
Brut Sparkling Wine

Photo: Richard Majchrzak/Studio D

Brut Sparkling Wine