A Gay Man Asks: Can I Wear This to a Formal Event?

Written by | Lifestyle

well dressed man POV

Photo by Sean-Pollock

It’s Saturday night and in about 15 minutes, I’m supposed to hop in a taxi headed for a swanky charity ball where everyone will be dressed to the hilt in their best formal attire. But instead of being in “Keys? Wallet? Phone?” mode, I am still on the other side of town, standing in my Calvins, staring at my closet.

Next to me is a huge pile of clothing that I have tried on, rolled my eyes at and torn off in fits of frustration. How could I have waited until the last minute when I’m attending an event where a well-planned outfit is positively de rigueur?

I try on my favorite Hermes suit before remembering that I wore it to this same affair last year. That’s out. I briefly consider my Ted Baker slim-cut magenta trousers with vintage powder-blue tuxedo shirt, but somehow I don’t think I’m feeling quite fabulous enough to pull that off. What about a nice, light seer-sucker? No, not right for an evening event. An Agnes B. gray suit with white shirt and blue tie? Not enough personality.

Time keeps on ticking, and I just keep finding myself back in my briefs. I’m momentarily distracted by a picture I have hanging in my bedroom. It’s of Marilyn Monroe in a black teddy and matching sheer dressing gown. She’s sitting in her boudoir in a deco-style club chair (upholstered in champagne velvet), eating chocolates with the very tips of her perfectly manicured nails. I’m jealous because she looks so put together, and she doesn’t even have to leave the house!

But I Have to Leave the House

I settle on Gucci loafers, plum slacks, a white linen shirt and a Trina Turk jacket (in a beautifully woven yellow and white jacquard). I manage to convince myself that it all looks rather dashing, but about halfway across town, panic sets in. People wear tuxedos to this event — am I going to be way too under-dressed?! What if I look like I should be in Palm Springs lunching with Bob Hope and Dinah Shore after a game of golf?

But I’m already running way too late, so I press on until I reach the hotel. The long escalator ride up to the ballroom gives me a chance to stare critically at myself in the mirrored wall, and I realize that I have become one of those people I loathe — the ones who show up to a well-planned and time-honored event wearing something completely inappropriate.

I sneak into the ballroom trying not to draw attention to myself. All around me are handsome men with their tanned, muscular necks framed by snug, white-wing collars and bowties, their shoulders clad in well-tailored jackets. I feel like I might as well grab a tray and start taking their drink orders.

As I begin to make my way around the party, I keep a wary eye out for anyone looking official enough to ask me to leave the event due to my non-adherence to the dress code. But then something strange happens: I hear perfect strangers whispering complimentary things about my ensemble as I pass. Partygoers strike up conversations with me by commenting on what I’m wearing. Men in impeccable tuxedos from the best fashion houses ask me where they can purchase their very own Trina Turk. A woman wearing hair too large to ever be successfully taken on public transportation thanks me for bringing a little sunshine to the evening.

Far from getting me ejected, the outfit becomes my signature, and soon I am flashing it all over the ballroom. Sure, I got the occasional sidelong glance from a purist who seemed steamed under his heavily starched collar that I wasn’t adhering to the letter of “black tie,” but what I discovered that night is that if you put some thought into what you’re wearing — if those colors, cuts and designers make you feel gorgeous — someone will appreciate it, whether you’re attending a ball, having lunch in Palm Springs… or even just staying at home and eating chocolates in your bedroom.

Looking for some statement fashion? Shop where P!nk, Madonna, Cher and Prince found some of their most staggering looks.

Last modified: August 8, 2018