Peggy Lipton
Actress (The Mod Squad, Twin Peaks, now doing theater and writing her memoirs); 55

Date style: "If I'm wildy attracted to my date, I'll wear something sexy; if it's more of a friend thing, I won't." She changes clothes a lot before going out, often four or five times. "It takes me a while. I'm never on time."

First-date advisory: "Look for friendship first," says Peggy, who is more protective of herself now than when she was as a young woman in the age of so-called sexual liberation.

Matchmaker feedback: This whimsical skirt is made of tie shapes in spring's candy colors; it's dressed down with a casual leather jacket. "People who dress stylishly can come across as standoffish—not Peggy," Samantha says. "She smiles a lot; she's a warm person. The outfit reflects that."

Leather jacket, $389, Isabel. Satin tie skirt, $640, Paul Smith Women. Necklace, Irene Neuwirth. Shoes, Gina.

Molly Shannon
Actress (former Saturday Night Live regular with a TV film—The Music Man, with Matthew Broderick—and two movies—The Guest, Good Boy!—coming soon); 38

Date style: Feeling natural is key. "I don't want to get so codependent that I'm always thinking of what other people like."

First-date advisory: "Be brave," says Molly. "It's scary simply to show up, to admit that you're looking—it's easier to go to the movies with a girlfriend."

Matchmaker feedback: Hip but polished, this mix of a cool silk-screened tank with a striped blazer and denim trousers (sleeker than jeans) "epitomizes casual chic," says Samantha.

Seersucker blazer, $500, and top, $165, See by Chloé. Trousers, $59, Ann Taylor Loft. Shoes, D&G.