It all seemed so promising. He was smart. He was employed. He lived in a Modern, art-filled loft in SoHo. And he was apparently big enough in his field that he had his own Wikipedia entry (albeit very likely self-penned).
As my potential match approached me on the night of our fateful first date, I clocked the few qualities I'd been unable to glean from Web searches (umm, stalking sessions): his height (tall, thank god); his hair (curly, there are products to alleviate that); his neat button-down (smart). But then his bag…oh God, that bag. A black nylon rip-stop messenger monstrosity draped over his arm and causing even his tall, muscular frame to bend sideways under its weight. What kind of successful, self-respecting thirtysomething man would walk around carrying a techie conference on his shoulder to a first date?
Needless to say, our courtship didn't last very long. I gave him two more dates—mainly because I wanted to see his apartment (this is New York, after all, where real estate is crucial). And there were other reasons—namely, chemistry—why we weren't meant to be. But I could never erase the mental image of that Silicon Valley sack. Had things gone more fortuitously, it most certainly would have been my first home improvement.
I don't need a planet-titled tome to tell me that men and women are fundamentally different in many ways. When it comes to how guys and girls instantly process the sartorial choices of prospective partners (or even friends), the chemical signals firing away in their brains are motivated by significantly divergent goals. I would like to call it the What Lies Beneath syndrome.
At the risk of unfairly simplifying the male mind (is that possible?), what they are registering from a woman's fashion choices is a matter of how those clothes show off or suggest the body beneath. Anything that hints at whatever sparks their hearts' desire—big breasts; long, lean legs; a flat stomach—will prove a winning ensemble. (Do you know how many of my male friends deplored the tent-dress phenomenon? As one particularly forgiving fellow put it, "You could take her home and realize you had been totally misled by what was under there.") Clothing to them is merely an algebra equation: x (butt-enhancing jeans) + y (boob-enhancing top) = z (sex, please).
Women, however, are performing calculus. An ill-fitting suit or an ugly pair of shoes or a Silicon Valley–worthy bag signifies not what bodily imperfection he might be hiding but who he is on a more cerebral and existential level. Artsy frame glasses: intelligent, sophisticated, well-educated. A Savile Row creation: exceptional taste, drinks his scotch neat, financially stable (or loaded). A perfectly rumpled button-down and Levi's 501s: easygoing, likes a good beer, open-minded worldview.
With such high stakes, it's inevitable that every woman has her own opposite-sex style dealbreaker, an instantly registered faux pas that inspires revulsion and, in some cases, fight-or-flight vital stats. I know one girl who shudders at the mere thought of a popped collar. And many ladies are self-described "shoe people," keeping their gazes resolutely directed downward for flagrant footwear offenses. (Sandals of any kind, bulky orthopedic sneakers and cowboy boots come to mind.) I'm not disgusted by murses—thankfully, such occurrences are rather rare. It's generally the lower half, the pants portion, that tends to strike me immediately, by either its elegance of cut or atrocity of existence.
There was the writer interview subject a few years ago who showed up in a burgundy velour tracksuit. Ignoring the fact that he had a Jewfro and was borderline morbidly obese, those thick, baggy bottoms the color of dried blood stopped me dead in my tracks.
Or the guy walking down Lexington Avenue in Midtown during lunch hour in eggplant sateen boot-cut trousers, looking like some long lost Bee Gees groupie.
And mom jeans? Well before our President demonstrated his lack of denim know-how, I'd been restraining my gag reflex when faced with a multitude of jean predicaments: high-waisted stonewashed numbers that bestow beer-gut bulges on the slimmest of men; purposely frayed cuffs that look like the scraps from a bath-mat factory; skinny cuts on not remotely skinny people, and those intricately bleached numbers from Diesel so beloved by Euros and Jersey guidos.
Some might call me shallow. I prefer observant. Or realistic. The thing is, just as with women, men's stylish (or unstylish) choices instantly telegraph something about their inner lives. Those track pants suggest slovenliness or an unhealthy interest in The Royal Tenenbaums. The purple shiny limbs? "I want to shag you and I probably won't be very good." And all those problematic denim cuts and washes? "I can't even get the basics right; I'll be hopeless with anything more advanced."
Obviously, it's not an exact science. Take my best friend in college, who came out during our senior year. I'd had an inkling about his sexual preference since we'd met as sophomores (the lack of girlfriends; the love of Sex and the City reruns), but every time I saw him, something about his outfit made me reconsider my suspicions. There were his baggy but not homeboy-style khaki pants with their unflattering legs and a very large break at the cuff. His New Balance sneakers were so sensible they bordered on geriatric. And when the weather got cold, he broke out this navy knee-length, Pillsbury Dough Boy puffed down parka that I could spot a block away and that we affectionately called "fat coat." No way this guy was gay; his genes would have given him better sartorial sense.
And yet it turns out he was, and my first impressions were nothing but a string of red herrings. (He now wears fitted sweaters, thanks to his far more aesthetically attuned husband.) That's the thing about style: It's a mutable entity. Which should be a comforting thought for those men prone to such glaring mistakes, which, let's be honest, are more often than not products of ignorance rather than premeditation. Consider this: If you're not thinking about what you're putting on, I won't even be thinking about taking it off.
What Women Notice In the First Nanosecond
Sophia Bush: "The first thing I notice is always shape, tailoring. When men are in beautifully fitted clothes, they don't have to be in anything over-the-top exceptional. But I can always tell when a guy is wearing a really great pair of pants, because of the way they fit."
Salma Hayek: "When he moves easily in his clothes. They can't be too stiff."
Vanessa Paradis: "What I like is just the way they are when you know they haven't spent too long on themselves—that they have gotten ready quickly and still look good."
Katie Holmes: "Cool jeans and cool T-shirts."
Christian Serratos: "Probably the jeans, if we're talking strictly fashion. If they hang really low, it just looks stupid."
Shiva Rose: "The way his jeans fit. You don't want them to be too baggy or too tight. The worst is when they are tight on top and loose on the bottom. Either do a skinny jean or a baggy jean—not both!"
Joanna Krupa: "It's just about the attitude, the way he comes into a room. The worst? Oh my God, those jeans where the boxers are showing— that has to go. It's been, what, five years? It's not cool anymore."
Eunice Lee, Unis: "I tend to notice bad style first: I'll think how horrible his jeans, sunglasses or shoes are. But when a guy has great style, it's usually because he's understated, so then I'll notice his eyes or face fi rst. The clothing should never overpower the guy."
Rachel Roy: "I notice intelligence, happiness and a good accent."
Lea Drucker: "I like the lived-in look. Serge Gainsbourg is my men's wear style icon."
Charlotte Gainsbourg: "His face."
Catherine Deneuve: "Probably the cuff links. I like men who wear cuff links."
Dita Von Teese: "It's important to notice the man, not the outfit."
Noémie Lenoir: "Beautiful jeans with a beautiful butt in it."
Ludivine Sagnier: "I always look at the shape of their trousers. The pants have to fit the legs well."
Kate Moss: "His jacket."
Aliz Goldwyn: "I'm a sucker for a suit!"
Rachel Bilson: "It's always the shoes. I like vintage boots."
Sienna Guillory: "Shoes and socks. The bits on the bottom are so hard to get right—very few men do. Like where the bottom of the pants meets the shoes….And a good pair of Italian shoes—nothing beats it."
Nathalie Rykiel: "The first thing I notice is the way he looks at me. A man can get away with almost anything. My favorite look is a T-shirt with trousers and a jacket, or a sweater with trousers slightly baggy, but not too much. The silhouette I detest is tight pants with a tight jacket."
Donna Karan: "When I look at a man, it's never one thing. I see the whole picture all at once."
Sarah Silverman: "I am turned off by cologne. I like a man to smell like a man."
Anna Mouglalis: "Something that is subtle, effortless. [The ideal is] to not see it at fi rst."
Fanny Ardant: "His skin."
Delphine Arnault: "His shoes…and his hands."
Lou Doillon: "I don't like men who look after themselves too much. I do like it when they're not wearing anything."
Rebecca Minkoff: "The fi rst thing I instantly notice about a man's style is the bag he's carrying. I look to see if the bag's been broken in, the shape, the color. You're able to tell a lot about the guy by what he carries."
Jenna Lyons, J. Crew: "Shoes. If the toe is square, I'm out."
Michele Hicks: "I look at the way his clothes fit overall. It doesn't really matter what style they are, I just don't like sloppy, like when things are too oversize. I like to see what's underneath."