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What We Wear When We Talk About Love: DateWear for Men
by Brett Singer
Modern dating has many pitfalls, not the least of which is deciding what to wear. For the heterosexual man, this often means changing clothes or greatly altering personal style. What works at home or with the "buds" may not quite do the trick with "the ladies."
For the fashion-clueless man, here are some tips for the first few dates that will hopefully nudge him on the way to dating success.
The First Date.
This is tricky. She probably knows what you look like (unless you met her online, in which case she could be a teenaged guy named Moe and this is NOT the article you should be reading). However, you most likely met her in a professional and/or social situation -- work, a bar or nightclub, a meeting set up by your mother, etc.
These are controlled environments, clothing-wise: you were probably wearing a shirt, a tie, and socks that matched. But now that you're on your own time, don't fall into clothing chaos. The location of your rendez-vous will likely be somewhere first-date casual -- keep your outfit simple and neutral. Go with a sweater and jeans or khakis. Primary colors are best, such as a black sweater with Levi's -- avoid patterned sweaters at all costs to avoid looking like Stevie Wonder is your personal shopper. If you live in New York, make it easy and wear all black.
Sneakers are probably fine, but pull out the clean ones. If it's too warm out for a sweater, you have two options: (a) put the date off until winter, or (b) wear a simple button-down Oxford-type shirt or a SOLID COLOR T-SHIRT. "Beer Goggle" tees or anything from a sports team are strictly out.
Date #2: Congratulations. Those clean jeans worked. Now it's time to go out for a decent dinner. This allows you to show her that you do, in fact, own at least one suit or sportcoat. Our advice: if it's a suit, stick with a plain white shirt and a tie with no extreme patterns or cartoon characters. For a less formal look, try an Izod-style golf shirt with the sportcoat, again sticking with solid colors to reduce the likelihood that she will discover that you are a walking fashion time-bomb.
Date #3: It's not an accident, she actually likes you AND your fancy coat. It's time to skip the whole "going out" thing and invite her to your place for dinner.
If you are more Oscar than Felix, cleaning your apartment is a must. Consider hiring a service (nothing turns a woman on more than a spotless countertop). Don't blow it by getting too comfortable and wearing the pants with the holes over the left cheek. Remember what you wore on the first date, and wear a variation on it -- a new pair of khakis, a different color t-shirt and shoes that match your belt.
By this time you will have a sense of the woman, as well as whether or not you want to take this relationship "to the next level." If so, wear clean underwear, and please, boxers, not briefs. For more information, check out our archives ("What Men Wear Under There: The Ins And Outs Of Underwear").
If you follow this advice, we don't promise that you will end up in marital bliss or even get a fourth date. But if it doesn't work out, maybe she's got a cute friend who has heard all about your fine date-dressing style.
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