Last weekend, I was reminded of a funny incident that happened back when I was living in London, England, just after graduate school. I was young and had yet to be introduced to the anxiety-ridden world of adult dating — where first impressions are premeditated and graded against the string of other first impressions filed under “awkward dinner dates.”

It was an Indian summer that year — a record breaker — and my friends and I had just returned from a weekend trip to the coastal county of Pembrokeshire. We were sunburned and thirsty; a trip to the pub seemed the perfect way to ease back into our work schedule after a weekend of sun and surf. And so, without stopping off at the house to change, we popped into a bar, not thinking twice about our beach attire. I was with two friends, both males and both dressed in shorts and non-descript T-shirts of the Hanes variety (a favourite of mine — especially the white), while I wore a simple sundress that smelled of Coppertone. I remember the Coppertone especially, that and the heat of my reddened cheeks as I did my best to burrow my face into the top of my dress as the pub door shut behind us.

“Name, profession and age… if you’re willing to share,” said a woman holding out a blank name tag and a marker. And so it was that we three became the unknowing participants of what I would later learn was a speed-dating event. As taken aback by the name tags as I was, they weren’t the giveaway; it was the sea of men and women dressed in cocktail attire at a pub famous for its Sunday night Scrabble tournaments, not to mention being — without exaggeration — a contender for having the worst restrooms in the city. Think Trainspotting.

The teeming pond of co-eds on campus made it impossible to comprehend why anyone would have to resort to something like speed-dating. Flash-forward to present day and see me in a club, surrounded by men and women dressed for a night of first impressions.

Granted, it was the closing night party for LG Fashion Week at Muzik, but even still, with the combined time that it probably took everyone occupying the club’s VIP space to get ready for the present party, SETI might actually have been able to locate life on other planets. Of course, I’m biased because I suffer from a syndrome that leads me to break out into a sweat every time I pick up a straightener, not in the least due to the heat from the tool. Still, the dressed-to-the-nines-part of that night’s company couldn’t be denied.

After my last experience at Muzik, where I felt like I missed out on a memo stating all in attendance should wear heels tall enough to elevate them to 5’9" or above in height, as well as dresses that flaunted as much as they glittered, I was extra conscious of not dressing like I was attending an art opening directly after accompanying my 5-year-old niece to a schoolmate’s birthday party. But, despite my efforts, I was still far from reaching the level of “doneness” that the other women in attendance had achieved. My three male escorts on the other hand, had hit the mark — or so the attention they garnered that night would suggest. I’d like to say it was the Grey Goose, but in the end, credit has to be given to the outfit each man chose that night.

Where one attracted the attention of a female would-be-L.A.-resident with his scruff of hair, button up shirt, skinny jeans and classic Blundstone boots, the other wrangled an aspiring actress with a taste for luxury by way of his smart bowtie (the irony is intrinsic when donned by the young and handsome), crisp white button-up and perfectly paired (not to mention tailored) navy blazer and fitted dark denim, and then there was of course the sensitive writer, in his shrunken tweed jacket and slim oxfords, who became the unofficial gatekeeper to the two other men, shuffling women away and hither.

The secret to the attractiveness of the three looks: effortlessness.

The world of men’s clothing is expanding, and is doing so in accordance with popular tastes that have men seduced by the debonair dress of Don Draper as much as drawn to the unkempt man-boy look Joseph Gordon-Levitt’s character in 500 Days of Summer epitomized. All in all, the current trends match the modern day dandy with his lumberjack beard and fancy for cigarette slim suiting. For this man, there is now The Bay’s Mens’ Contemporary Designer area (formerly known as The White Space for men), the male answer to The Room. Located on the second floor of the flagship Queen Street store, brands carried range from the hipster-preferred designs of Band Of Outsiders, Surface to Air and Opening Ceremony, to ready-to-wear items selected for GQ/Rolling Stone-reading professional types, including Filippa K and Save Khaki, while also offering its more ruggedly fashionable clientele, the quintessentially masculine Klaxon Howl collection, a Canadian favourite amongst vintage connoisseurs.

My suggestion to the male shopper: regardless of your target market in the world of singledom, it is always wise to skip the L.A. casual look. Say no to rolling up your skin-hugging khakis, and shout no to pairing even unrolled khakis with TOMS. A woman — an adult woman who isn’t impressed by where you DJ on the weekends — can trust a man who knows how to pair a bowtie with a discreet sense of style.

Toronto-based writer Jennifer Lee is the Editorial Director of FILLER magazine, an online fashion & culture journal. She is also the Co-Editor of Hardly magazine, an arts-centric online teen publication for Canadian girls. Her column, The Dressing Room, appears weekly.