Photo: Steve Prezant\Blend Images\Corbis.

Most men will tell you they don’t spend a lot of time checking out your bra and panties. This is true and not true. The first time we get it on with you, we’re too psyched to appreciate your frilly La Perlas. After that? We notice. And we draw conclusions. Here are a few.

Fancy lingerie says: “I will be your boss one day.” My friend Jeremy,* 32, recently left a work party with his office crush, Tina, a fellow attorney. He was bowled over by her lacy bra and thong. “They matched and looked expensive,” he remembers. Sure, Playboy models wear coordinating undies—but so do very professional, put-together women, which is a turn-on. As Jeremy puts it, “Dude, she doesn’t miss a thing. She’s laser-guided.”

Wearing nothing says: “Let’s get it on.” Shia, 25, works at a bar, where my friend Leo, 30, met her. The first time they hooked up—after she IM’d him late one night—he got a surprise. “There was nothing under her dress,” he says. That lack of undies told him one thing: “This was about sex.” And Shia and Leo are now happily enjoying that one thing on the regular.

Spanx say: “I needed to look hot in my dress tonight.” Guys get it. That stuff’s your chain mail armor against the world’s attacks on your imperfections. Just don’t wear it to bed.

Colorful, unmatched undies say: “I do what I want.” My buddy Tyrone, 28, recently hooked up with Jenn, a 25-year-old grad student in sheer neon-pink boy shorts and a yellow bra. He was smitten. “Jenn is not worried what some guy thinks of her underwear,” he says, adding, “I want to text her so badly. Do you think I should text her?”

White basics say: “I’m comfortable in my own skin.” Every guy has his weakness. Mine’s white cotton panties, because they’re not trying too hard to please me. And if you wear them on date night, it shows you understand guys, lingerie, and this simple, self-evident truth: What you’re wearing under your clothes doesn’t matter nearly as much as how you wear it. It’s the wrapping paper—by the time we’ve ripped it off, we’ve forgotten it, and we’re all about the present.

Jake is a real single guy dating in New York City.

A Girl’s Guide: What His Underwear Tells You About Him

George Kotsiopoulos, who skewers celebs on E!’s Fashion Police, critiques your guy’s shorts.


He drinks scotch, wears banker shirts, and does all the driving. This man is not into upending gender roles. On the plus side, he’ll open doors for you and pick up the check.

Boxer Briefs

They’re a little racier than classic boxers; he wants to be sexy but not a pansy—manly sexy! But the name on the band? No! Why would a guy want another man’s name near his genitals?

Tighty Whities

Either his mother is still buying his underwear, or he’s so charismatic he can defy fashion, ignore modern advances in male intimates, wear “underpants,” and still somehow get laid.

Silly Undershorts

No matter how conservatively he’s dressed on the outside, this guy’s fun, and you’re going to have fun with him. You wear kooky underwear, what’s the rest of your life going to be like? Fun.

*Some names have been changed.