Indira Cruz
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.

Sharon Alouf
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.

Sonie Maclaren
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.