Alexandra Wentworth in O Magazine

Grecian Turn
While Wentworth's go-to evening wear is most often a long black sheath (suitable for life in conservative Washington, D.C., where she lived for the past seven years), she felt the pull of one of this season's seriously short—and beautifully draped—jersey minidresses (Derek Lam, $1,490). "I'd wear one every single day if I could be airbrushed in life," she says.

Bracelet, Rosena Sammi. Necklace, Shourouk. Heels, Proenza Schouler
Alexandra Wentworth in O Magazine

Like Butter
Warm-weather leather? Sure. The latest pieces, like this body-hugging shift (Ralph Lauren Black Label), come in soft colors and weigh next to nothing, which means they look sophisticated and feel light and easy. "I don't dress provocatively, but in a short dress, you feel sexy," says Wentworth, the mother of two daughters, 4 and 7; husband George Stephanopoulos is a coanchor of ABC's Good Morning America.

Necklaces, Robindira Unsworth. Bracelets, Adesso and Kevia
Alexandra Wentworth in O Magazine

High Impact
The It bag has been officially usurped by the statement shoe (Louis Vuitton): Think lots of personality and plenty of details like bright colors, straps, studs, and architectural platform heels. Looking glamorous in a turquoise gown (Diane von Furstenberg, $825), the former Head Case star says she loves the lift a bold pair of heels gives to her everyday black pants.

Earrings, Genevieve Jones
Alexandra Wentworth in O Magazine

Plenty of Flak
"I think I take risks in life more than in fashion because I'm terrified I'll be made fun of for wearing something flashy," says Wentworth. These urban fatigues—a military jacket (Smythe, $650), tank (7 For All Mankind, $68), and cargo pants (Rare Donna, $254)—felt right to her, even as a head-to-toe uniform. "I wasn't sure about cargo pants with high heels, but they look incredibly feminine together," Wentworth says. "Jumping over fire in them is a little difficult."

Dog tag necklaces, David Yurman and Tom Binns for Disney Couture. Pin, Ben-Amun by Isaac Manevitz. Cuff, Vita Fede. Ring, Kardashian for Virgins Saints and Angels. Belt, Melamed. Shoes, Guess
Alexandra Wentworth in O Magazine

Balancing Act
What keeps spring's voluminous pants (Urban Zen, $795) from making you look like you're in, well, the circus? Fabric that flows into a tapered leg. "With a tee and flats, anyone can get away with this," says Wentworth.

Top, Yigal Azrouël, $290. Necklaces, Camilla James and Helen Ficalora. Belt, Melamed. Bangles, Irit Design. Sandals, Vouelle
Alexandra Wentworth in O Magazine

Jumble Love
Suspend your disbelief: You can mix the season's tribal patterns (tank, Nicole Miller Collection, $275; jacket, Suno, $475; pants, Dries Van Noten), especially if you stick to similar shades and vary the scale of the motifs. Not that extroverted? Start off with a patterned blouse over neutral pants or a skirt. Layers of bold baubles work well here—whether they're African beads or, for inveterate flea-market shopper Wentworth, colorful pieces found closer to home: "I lean toward big jewelry."

Earrings, Kenneth Jay Lane. Necklaces, Jennifer Elizabeth and Sissy Yates Designs. Bangles, Diane von Furstenberg and Colette Malouf. Ballet flats, Matt Bernson
Alexandra Wentworth in O Magazine

Ready For Takeoff
The last time Wentworth wore a jumpsuit, she was diving out of an airplane for a segment on The Oprah Winfrey Show for which she is a frequent correspondent. The one-piece, made famous in the '70s by designers like Halston, reappears this spring with a blousy top half, dressy fabric, and feminine shape that steers clear of flight-mechanic comparisons (Zero + Maria Cornejo, $898). "It's unbelievably comfortable. I thought only tall, skinny women could wear jumpsuits, but that isn't true," says Wentworth.

Bracelet, Cocobelle. Bag, Louis Vuitton. Belt, L.A.M.B. Pumps, DSquared2

Get the look for less! Great summer buys under $100