I’ve never been a big fan of Valentine’s Day—except, of course, when I was a kid and would spend the better part of a day constructing an elaborate Valentine’s-catching shoebox, complete with red and pink tissue paper and foil feathers. (Have I mentioned that I love to craft?) Anyway, it’s always seemed like one of those holidays that intends to make single people feel badly. And as I was a single person in New York City—for, what, seven years?—who relied on restaurants to keep me fed every night, the holiday was always a double blow, because you couldn’t get a reservation, and should you find a seat at a bar, you were always bookmarked by awkward “are we exclusive yet” couples and tired married people going through the motions. I might have expected “romance” when I was eight, but let’s just say that my V-Day expectations had waned considerably over the years.
Anyway, three years ago, Valentine’s Day fell on a Saturday: It was cold in New York, and I set out to meet my friend Sarah for a matinee and a post-movie wander in a hoodie (never go to the movies without one), Rod Laver sneakers, a beaten up pair of jeans, and a truly messy bun. I think we fell into a spell at ABC Carpets because suddenly it was late, and so I had to go straight to a birthday dinner at my brother’s apartment for my brother’s partner’s little brother (22 at the time) without stopping at my house to change. From there? We made an unanticipated pit-stop at a Valentine’s Day party at one of my brother’s author’s houses in Soho (it was on my way home). There were 11 of us at the party in total, in an unfurnished loft, and so we used the empty floor-plan for an impromptu dance party (so not my style). At midnight or so, my friend Lori texted me that she was at a birthday party down the street from my house in Nolita, at the bar that I frequented most often, called Shebeen. Naturally, I extolled all 11 party guests to accompany me there, where I ran into this guy Rob, who I had met a couple of times through my friend Nick. And by met, I mean that we had stood awkwardly at Shebeen together while Nick and Rob chatted. Rob was an interior designer at the time for Armani Casa (I found that last part really confounding): I thought he was very good-looking (if you live in New York for long enough, this can actually be a turn-off/warning sign) and maybe boring (he’s super shy), and clearly disinterested in me (he assumed I was dating Nick, and so had refused to engage me in conversation at all).
Still with me here? There we were at Shebeen on Valentine’s Day, and after we established my relationship status, and the fact that Rob wasn’t shy but was actually awesome, he told me that he liked my hoodie. I figured it was because it made me stand-out in the sea of party dresses and high heels. But in reality, I think it was because that’s actually what I’m about. Dressing like a boy…but with lots of jewelry. We went out on our first date two weeks later, and I tried to compensate for the fact that he’d essentially seen me in my PJs by pulling out the big, fashion with a cap F guns: Some crazy, drape-y Gary Graham top, really high boots, a leather jacket, makeup, blown-out hair…and he was confused. He missed my hoodie and my arguably ratty curls. I guess what I’m trying to say in my long-winded way is that A. You really never know when you’re going to meet the guy you’re going to marry. And B. It’s arguably best for everyone if you’re wearing something that approximates your real-life personality and style. I may work in fashion, but I still think life is too long for endless dress-up. So while I have to admit I’d never show up to a first date in my Valentine’s Day outfit, I do believe you should look like an ever-so-slightly more polished version of yourself. I mean…right? What’s your take?
And happy Valentine’s Day! I may still hate on it, but I owe this holiday a lot.
clockwise, l-r: ADIDAS ROD LAVER SNEAKERS, $59.95, Nordstrom; UNISEX HOODIE, $51.00, American Apparel; JAMES PERSE V-NECK T-SHIRT, $50.00, Neiman Marcus; RAIL-STRAIGHT JEANS, $98.50, Madewell.