I knew it would cause a stir when I began wearing neckties in high school. Striped and plaid private school ties readily available at Value Village were a simple way to not look like everyone else. Especially when rakishly loosened, for me they evoked a romanticized world of British prep schools and ‘Brideshead Revisited.’ That’s not how my classmates saw them.

“Ha! Avril Lavigne!”

“No,” I protested. “I’m a guy. Neckties were our thing first!” Silly peasants: my classmates couldn’t see that by wearing one as a woman, Avril was doing the subversive thing, not I. And it wasn’t just teenagers who misinterpreted them. One of my father’s friends (most likely a former hippie, a New Democrat almost certainly) actually rolled his eyes at me. Noticing that it was casually loosened he said, “I guess if you’re going to wear a tie, that’s the best way to do it.”

For him, neckties represented conservatism and conformity, the authority from which he rebelled in his youth. Not ever having been forced to wear a tie, I saw their formality as fun and just a tad rebellious. Classic items like neckties may change very little, but our reactions to them definitely do.

Where once formality was the rule of the game (men had to wear hats and ties, and women dresses), now casual clothes are so pervasive that those same formal items are the things that are unusual. The old adage has reversed: it’s now better to be underdressed than over. True, many offices still have dress codes, but with Casual Friday’s march of domination, our standards for dressing up are constantly being watered down. How else to explain a conservative, athletic, not un-handsome man like Paul Ryan wearing nothing but ill-fitting suits and shirts so baggy he swam in them during the recent American election?

Though men can get away with dressing more schlumpy than women, the same sort of enforced casualness applies to ladies. If a woman wears feathers, hair jewelry, a cape, or any other of the glitzy items that fashion magazines insist will be ‘in’ each season, she will have to answer skeptical queries about why she dressed up when everyone else is wearing leggings.

Case in point: earlier on this site, I assumed that comedienne Mindy Kaling’s new show ‘The Mindy Project’ wouldn’t really be about fashion. After all, it’s a workplace sitcom and she plays an OBGYN. But then I actually started watching it. (Yes, I may be the only one.) In one episode, Mindy dresses up for a date in a sparkly, sequined top that makes her feel “fierce.” But her male colleague tells her that that’s not the type of clothes guys like and she should just keep it “sexy and simple.” Although she argues with him, he runs into her later in the elevator wearing a curvy red dress with nary a sequin in sight. I was disappointed that someone who has as many opinions about clothing as Kaling allowed her character’s fashion choices to be influenced by a man. In a later episode, when she jokes with a boyfriend that she’ll wear a football jersey to a Superbowl party and he balks, she turns dead serious: “I’ll wear what I want.” I wish that sentiment had come earlier.

My fashionable friend’s sister got married this summer and because getting married is a concept so foreign to either of our lives right now we looked upon it like outsider anthropologists. Reality TV didn’t prepare us for the number of pre-wedding parties (three), or all the drama of bridal gown shopping.

“I guess I’m not a manicure kind of girl,” my friend said, having spent all afternoon getting her nails painted a bridesmaids lavender.

“Of the two of us,” she continued, “I’m the girly one. My sister doesn’t dress up or wear makeup very often. She probably thinks her wedding is her one big chance to wear a fancy gown and look beautiful. But the thing is, you don’t need a wedding to do that. On any Saturday night, if I want to wear a big lace dress, I just do it. You don’t need a big party to justify it.”

I was never prouder of my friend’s amazing personal style than I was in that moment. You don’t need to be sanctioned to wear something fancy–you just need the bravey to deal with the attention and the comfort with yourself to pull it off. Ultimately, I guess it’s not about formal versus informal. It’s about having the courage of your couture. 

____

Max Mosher writes about style for Toronto Standard. You can follow him on Twitter at @max_mosher_. 

For more, follow us on Twitter @TorontoStandard or subscribe to our newsletter.