Actress (upcoming movies include Boat Trip, with Cuba Gooding Jr., and Basic, starring John Travolta and Samuel L. Jackson); 29
Date Style: "Maybe it's a Latina thing—I like to look sexy." She won't go out without high heels. "I feel leaner and taller in them."
First-date advisory: "If a guy says, 'I wasn't faithful to my last girlfriend,' pay attention. Don't think you can change him."
Matchmaker feedback: "Wearing color makes you seem more accessible," says Samantha Daniels (her company, Samantha's Table, not only fixes people up but coaches them on their social life). "These shades are soft and spring-like and look good with Roselyn's skin and hair."
Suede corset top, $150, Andrew Marc. Silk skirt, $850, Ralph Lauren Collection. Ring, Baccarat.
Jana Marie Hupp
Actress (she plays Nancy Burton on NBC's Ed); 38
Date style: "I don't ever dress up for a date—in fact, I don't even call them dates: We just hang out and see if we want to go out someday." She likes low-slung jeans, vintage tees, boots: "I generally am who I am, take it or leave it."
First-date advisory: "Meeting a guy—the Cinderella thing—isn't the be-all and end-all. It's a big mistake to tailor yourself to the man. You'll make yourself schizophrenic."
Matchmaker feedback: This eclectic mix—a cropped Chanel jacket with jeans—gives a sense of Jana Marie's fashion panache as well as a glimpse of bare stomach. Samantha says, "Showing a little bit of skin is fine."
Wool jacket, Chanel. Cotton tank, $145, Philosophy di Alberta Ferretti. Jeans, A Gold E. Beaded scarf (as necklace), Chan Lu at Fragments.
Fashion Editor, Bartender; 27
Date style: Jeans, flat shoes, something black on top—"very low-key"—is her usual going-out look. Comfort is paramount. "I'd wear tennis shoes with a prom dress! I'm not about killing myself for beauty."
First-date advisory: "Always have a backup plan if the evening doesn't work out."
Matchmaker feedback: "These capris are a great alternative to the jeans Indira usually wears—much lighter and more fun," Samantha says. And the pattern mix—checked pants with a polka-dot top, and the baby-blue blazer, all in candy colors—makes it clear she made an effort. "A guy wants to feel she cared enough to think about what she is wearing."
Cotton pants, $46, Mystique pants by Dockers. Blouse, Arden B. Leather blazer, $450, Andrew Marc. Sandals, Tod's.
Jewelry Designer with her own company; 36
Date style: "I dress to bring out my feminine side, show my neck and shoulders. I'm stylish but not overpoweringly so. I try not to intimidate." Always wears: gold and silver minihoops. Her jewelry is rich-looking but never glitzy.
First-date advisory: "Let your guard down, be honest and stay clear. Don't censor yourself because of what you think his reaction is going to be."
Matchmaker feedback: Samantha pronounces this outfit "sexy and slimming." "Black can sometimes look too severe; here it's flirtatious and romantic." The bright earrings and shoes give it a sense of fun.
Cotton top, $495, Behnaz Sarafpour. Silk georgette skirt, $218, Eileen Fisher. Beaded earrings, bracelet, and rings, Sharon Alouf. Shoes, Jimmy Choo.
Fashion Marketing and Public Relations Associate; 26
Date style: At five feet seven, Sonie is the shortest in her family, so she loves the height-enhancing power of heels: "I wore my stilettos even when I was dating a guy my height." She is a fan of "great, dangly earrings" and always wears an emerald ring that belonged to her mother.
First-date advisory: "Have fun. Don't be too serious. And you've got to be comfortable; that's huge."
Matchmaker feedback: "Sonie usually wears a lot of black," Samantha says. "These soft purples and blues are much better for her." Asian influences are strong now; the quietly sexy cutouts under the sleeves of this top are part of a traditional kimono design.
Viscose top, $525, See by Chloé. Jeans, $121, 7 for All Mankind. Earrings, Kaviar. Shoes, Christian Louboutin.
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.
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.
Model, Actress, Entrepreneur; 52
Date style: "As a tall woman who speaks her mind, I can be intimidating," Alva says. So she softens the effect with a feminine dress, "or a top that says I have curves. I believe in showing what you've got." Jeans? "Only if I'm going bowling."
First-date advisory: "Be yourself, because it would require too much work to do anything else."
Matchmaker feedback: "There is a subtle suggestion of flirtatiousness here," says Samantha. "This dress has a lot of movement, and the color brings out Alva's natural rosiness. She seems happy and approachable."
Floral chiffon dress, $340, Diane von Furstenberg. Earrings, $320, Nava Zanavi. Gold necklace, Gold Avenue. Shoes, Anne Klein.