If You Want Your Dates to Be More Eventful, Start Dressing for Them

eadce194e1c80717908b0a1e924866abSince I’ve been single, which hasn’t been all that long, I’ve been on three dates. And would you believe two of the three were rocking a hat. Two!

And not a hat meant to keep your head warm, nor a hipster/barista’s “I didn’t shower” knit cap, mind you. But a gentleman’s hat. And while any single piece of clothing isn’t going to make or break a person necessarily (though there are exceptions), a man who’s dressed like a grown up, not an undergrad, wins big points. Ladies, there are men who make a fucking effort and, yes, it does matter.

I’ll say the same for women (as I said here), that first impressions count. Period. As you and I well know plenty of women balk at the idea that they should be judged by their appearance or attire. They think of it as unfeminist. They get enraged at the idea. But I think that’s silly. A bunch of bunk. Sorry–you can’t look like a slob and expect men to be attracted to you. Doesn’t work that way. Show me a person who gets really pissed off at the idea of being judged by their looks and I’ll show you someone who doesn’t like their looks.

Of course we all care about MORE than just looks. You’ve got to have more to offer than just eye candy. That goes without saying. But the looks up front do matter. And what makes me happy is to see men stepping up in that area as well.

But yes, hats are back. And I for one, am charmed by it. It harkens back to another era, when men wouldn’t be seen without one. Rakish looking men from the 1920s; dashing, fast-talking men from the Twilight Zone; Indiana Jones (need I say more?). I yearn for the days when men dressed to go out, before the sporting-goods-passing-as-wardrobe era. Which is why I honor the man who makes the effort.

The first date was a retired air force sergeant in his early 40s who told me, since we’d never met, to look for the guy in the porkpie hat. And there he was, waiting for me in the wine bar with a glass of red for me (points for classy). He turned out to be quite the gentleman: tall and comfortable in his own skin, worldly and kind, sensitive. I could tell he wore his hat with a sense of humor, not a thumb-your-nose, “Oh I’m so ironic” way. He genuinely liked wearing it, and I thought that was cool.

You gotta have a certain level of self confidence to rock a hat, to be sure. And you can’t take yourself too seriously. Wearing a topper indoors requires an innate or highly cultivated sense of style and self. True, too, men don’t really get to have too much fun with what they wear–what are their options, really. Button down? Khaki pants? Bore. But if you’re willing to go beyond the Standard American Dress, it says something about you.

Which is why I gotta hand it to my other hatted date, who met me at Cafe Tallulah, a stylish French bistro with easy charm, perfect lighting, and dollar oysters til 8pm. He wore a shirt, vest, tie, and a classic men’s hat, and drank scotch on the rocks. We spent two hours together, talking about our careers, families, the dating terrain in Manhattan. What we found important in other people and potential partners. And I made sure I complimented him, too–I knew he’d stepped up his game for the sole purpose of meeting me, and that alone was a lovely compliment to me.

Men, if you feel like you don’t know how to dress properly, don’t stress. There’s plenty of inspiration and ideas online nowadays that make it easier to develop your style. This online clothing store in particular has plenty of trendy and on-fashion clothing items and accessories to make sure you look your very best, on and off a date.

So if you want to date people, start dating. Stop with the whole bullshit “yeah we’re just hanging out” thing, rolling up to the bar or restaurant in unwashed jeans. It undermines your efforts to do what you want most: To meet someone who matters. The only way to make a shift in an uneventful dating life is to make it an event. Something you not just show up for, but dress for.