Courtship is over. Romance, dead. The idea of dating is hopelessly dated. So argued the New York Times last month, claiming that the younger generation traded dinner and a movie for text messaged booty calls. But if this is true, why are young women’s closets still filled with the Little Black Dress? Why is Instagram crowded with pre-going out self-portraits? Somebody, somewhere must be going on dates, and when they do, they still want to look their best. What exactly does that entail? How, in 2013, do we get dressed for dates?
To answer that question I did an entirely unscientific survey of my friends. Their responses ranged from unsurprising to scandalous. Generally speaking, people want to look put-together, but not contrived, and fulfill their dates’ expectations while being true to themselves.
“I think when I go out on a date I actually try to dress myself to what I want that person’s idea of me to be,” says actor Amy Kitz. “Or perhaps what I think they think I am…” If a guy sees her as a girly girl she’s likely to wear a “flouncy dress.”
“I have never even once considered buying a new outfit for a first date. I’m choosing from the clothes I already own and hence are intrinsically ‘me’… Mr. First Date can find out that I rarely wear dresses later on–no need to tell him right off the bat.”
Samantha ‘Sam’ Pockele, a research analyst who’s studying anthropology, admits she doesn’t go on a lot of formal dates–“There is only so much wine one can politely consume while pushing food that doesn’t contain garlic around one’s plate.” But when she does, she’s influenced by everything around her, including what she’s just watched on TV. “Perhaps I watched New Girl while I was getting ready. I’m showing up in a full-skirted lace sundress and heels with a cutesy owl-themed necklace. That night we’re ordering dessert, and you better kiss my neck at some point.”
Men are also influenced by what they think their dates expect from them. (Well, at least gay men are.) Retail manager Giovanni Guillaume says he choses things from his wardrobe to reflect different aspects of his personality. “When I went on a first date with a civil worker who was ten years older than me, I went for a more mature look of nice jeans and flattering polo shirt. Whereas when I got on a date with a trendy bar-tending West End-er, I pull on my Topman best.”
Across styles and subcultures, wearing black is a common preference. Writer Erica Yudelman says that almost all of her date clothes are black–“lovely, slimming, neutral black.”
Sam declares “black is my new black this year.” She describes her current favourite look as “high-waisted black spandex pants, knotted t-shirt, patent leather Steve Madden Mary Janes, Clinique lipstick in Red Red Red. If you show up and I’m wearing this, we’re probably making out at the end of the night, because I like you already, sailor!”
Although she has a soft spot for pretty pink, writer Alyssa Garrison claims she’s a sucker for the Little Black Dress. “The most popular at the moment is a black sweetheart neckline with a full skirt and heart-shaped cut out in the black…There was a short time during my new lesbian phase where I sported a leather jacket on romantic outings, but I think even that was still paired with one of my many LBD’s.”
People want to look well dressed, but in a nonchalant, effortless way.
“When dressing for a first date,” says Sam. “My consideration is focused almost entirely on looking like I didn’t put any consideration into dressing and just happened to rush in looking fabulous from the last spectacular thing I was doing,” even if that last thing was “asking my cat if I should change between screaming Nicki Minaj into my hairbrush.”
“I want to look cute,” says Sarah Portway, “but also accidentally-sexy, as if I never realized that my deer necklace gently leads his eye to my ‘best features’.” Portway, whose book on sustainable clothing production will be published this year, says that she tends to dress more formally than the men she goes out with. “I’ve been told my vintage-throw-back look can be intimidating, so I try to play it down a bit on the first few dates.”
Other women were not concerned at all with looking too formal. Alyssa admits that she has “this deranged idea that no matter how overdressed you are, you will always look better overdressed then underdressed. So I pull on sparkle tights and sequined berets for even the dingiest of bars with a strange sense of calm. I’m sure I’ve frightened a few potential lovers away…”
If someone makes you feel bad about your style, it might be a good indicator that you are not soul mates.
“Last month I wore a killer Narciso Rodriguez shift dress and Isaac Mizrahi lace-up feels for a first date,” says Sam. “Homeboy proceeded to take me to Starbucks and scoff at me when I ordered green tea.” After getting a “rescue text” from her friend, Sam took off to “slam cocktails” with her down the street. “I called up another dude for a random first date because there was no way I was wasting that look or that professional blow out. We went to a quiet bar where we drank wine, made up stories about other patrons, judged people younger than us, and basically had a ball…I don’t believe in being embarrassed. If you feel you look smashing in something, elevate your surroundings and celebrate it.”
Sarah describes a walk in the forest with a botanist. “I wore ballet flats and jeans, and he immediately pointed to my shoes and asked if I was going to be okay. I was pretty embarrassed, until I realized he was wearing those individual-toe-shoes and so obviously he was just displacing his own insecurities.”
Men, watch out for footwear!
Distasteful shoes were my friends’ number one dating faux pas, some going so far as to call them deal-breakers. Erica cites white sneakers as an issue with her ex, and Amy rants about a pair of “hulking rat-tail-laced, poop-hued hiking boots” a guy always wore. “In the dead of July! Wasn’t he hot? Weren’t his feet just constantly boiling? I decided it would be impossible to have a summer fling with him in those heavy shoes.”
Shoes aren’t the only mistake that will end a relationship before it starts. “Be yourself…to an extent,” warns Sam. “I will end the situation after two drinks if you are wearing the following: sandals, a necklace that incorporates seashells, a Doors t-shirt, glasses that are not prescription, a fedora, un-ironic pinstripes, or any Axe products.”
For most of my friends, what’s under their clothes is as important as the clothes themselves, and I’m not talking about their personalities.
Sam likes wearing seamed stockings with a matching bra and panties. “It doesn’t really have to do with the guy at all. It’s about me. It gives me personal confidence, and as trite at it may sound, confidence is the key to getting through any date successfully.”
Giovanni’s favourite underwear are boxer briefs with buttons down the front and an anchor on the waistband. “So nautical! My underwear, or at times lack there of, are a very good indication of whether I want the date to be a sexy one or not.” He admits to sometimes to going commando or wearing a jockstrap for “Let’s get down and do this!” scenarios.
Sometimes Giovanni’s hiding more than a jockstrap under his clothes.
“About three years ago, I had just signed up for Plenty of Fish and had started to semi-regularly date two guys,” he says. One was a romantic, cultured businessman. The other was an adventurous Scottish soccer player. “It was hard to choose between the two, so I decided both would do.” The night before he planned on going to a musical with bachelor number one, Giovanni made the mistake of letting bachelor number two come over and stay the night. “I wake up to find a dark round circle of a surprise planted like a target on my neck. Not couth!”
After work, he went straight to The Bay to buy a turtleneck to hide the hickey. “Not the most fashionable thing on the market.” Eventually, he found one and wore it to the theatre. Bachelor number one made jokes about it, but was none the wiser. “I thought I had executed the whole thing really well, but a couple days before Christmas, he shows up at my work with a box of cupcakes. He immediately zeroed in on the wine stain coloured bruise on my neck. Stupidly, I completely forgot I even had it, so I actually asked, ‘What are you staring at?’ He responded, ‘What appears to be a massive hickey on your neck. Merry Christmas.’ He swiftly stormed out. I think the embarrassment had me a healthy colour of red for a whole hour.”
But despite our best efforts, single people don’t always stay single forever.
Amy has been dating her boyfriend for a year and a half, “which means sexy wear is clothing that has been established as sexy through circumstance, not actual ‘sexiness’. I have this over sized pink men’s button up that I used to grab as my cover-up-as-I-walk-past-the-window-so-strange-balcony-dwelling-neighbours-don’t-see-my-butt outfit when I lived alone in Montreal. It really doesn’t cover anything up–it is more of a diplomatic gesture to the neighbours. When my boyfriend and I started dating, he used to comment on it all the time. He teased me for being a secret exhibitionist when I dashed past the window, ass exposed, nipples flying. Now we both live in Toronto with multiple roommates and even quick dashes to the washroom require serious coverage in order to keep the household peace. These days when I put on that shirt it takes us back to when we first met, when we had sex with horrifying frequency, and lived in cheap Montreal studio apartments where we could cook breakfast naked and drink wine with our tits hanging out. That ugly shirt is the sexiest piece of clothing that I own.”
Be that as it may, Amy needs to find another piece of clothing to wear for Valentine’s Day this year.
“I’m going to the opera,” she says, “so I certainly want to pay homage to the glamour and glitz of opera patrons. But I also don’t want to sit through five hours of Wagner in itchy tights. It will be a tough call. I will most likely decide last minute based on how bloated dinner has made me. Level of bloat is usually the top deciding factor of all my outfits. I probably have some gastronomical issues that I need to deal with.”
Erica’s office has organized a Valentine’s Day dress-up competition with a mini-trophy for the winner. “I may just wear all black and ruin everyone’s day,” she says.
Sam is hosting a speed-dating event tonight. “I like to dress like the CEO of Drag Queen Enterprises,” she says. “Zippered micro miniskirt with lips printed all over it, low-cut black knit top, vintage mesh and feather fascinator, glossy black eyelashes, sky high heels, knockoff Tiffany rings on as many fingers as possible. They say ‘dress for the job you want.’ I say, ‘dress for the dares you want all these lonely bastards to have.’”
I know when I see women out tonight in lovely dresses with their hair all done, I’ll take it to mean romance is not completely extinct. But I also must admit this holiday brings out range of extreme feelings in people. When I asked Sarah what she was wearing this Valentine’s Day, she answered, “Sweatpants and a bottle of Vodka. Thanks for rubbing it in.”
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Max Mosher writes about style for Toronto Standard. You can follow him on Twitter at @max_mosher_.
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