Why fedoras are stupid

We sit a few feet away from each other, separated by a cubicle wall. I write pop culture. She writes culture. I write about sex, social media and celebrities. Talya writes mostly about European graveyards. Then one day she ends a relationship, and I begin a strange new relationship with my mother, and we both start going on a lot of dates. Her first date since her breakup was spectacular! They talked for hours about literature and poetry.

My last date was dull, I tell her. And they do. The next night, Talya and I run into each other in the company bathroom after work. We put on lipstick side by side in front of the mirror. And worse, that guy who she had the hours long date with went on a date with someone else and he feels seriously about that woman, and now he just wants to be friends!

A long silence follows. Talya is laughing. She suggests we celebrate with a selfie. She wraps her arms around me, snaps a pic, and sends it to Josh. As the days shorten and the High Holidays appear over the horizon like a summer storm, I use Talya as a sounding board. His career prospects. A thrill of dread runs through my body, like a mouse feeling the high-voltage shock of an electric trap before sizzling to death.

Granted, Josh advertised his fedora in his dating profile, but I had assumed it was more of a commentary on the flaccidity of contemporary masculinity than an actual fashion choice. But Talya confirms that the hat made an appearance on their date. We sit, facing each other, at a tall table. My chest keeps doing a thing that feels like that moment when something made of glass catches the sun.

He loves chess. He keeps Shabbat. I find the fact that he wore a windbreaker to The Dakota Bar oddly attractive. He seems to accept this. Cotton, straw, wool, and leather are just some of the materials used to make this hat. At first glance, it's easy to understand why a trilby might be mistaken for a fedora. Both have crowns with a center indentation and pinches at either side. But trilby crowns are typically pointier than fedora crowns.

The short brim size of the trilby is its most defining feature. This stingy brim hat is indeed among the stingiest with virtually no protection for the eyes or face. Even flat caps and ivy caps provide some amount of sun protection for the eyes. This brings to light a major gripe people have about the trilby: It really only serves as a form of fashion with zero function. What's more, trilbies are often worn at the back of the head like a halo hat rather than leveled above the eyebrows.

And because of the smaller brim, a trilby almost always looks way too small on the person wearing it. While fedoras come out ahead in the trilby vs fedora debate, there are still some seminal pop culture moments that have been punctuated by the trilby hat.

For instance, even though Frank Sinatra is synonymous with the fedora, he also wore trilby hats. But he was only 5'8" tall and quite slender in his earlier years, so a small-brimmed hat didn't look odd on his narrow frame.

Plus, the man was a musical and style icon — he could pull off any look he wanted. Sure, it looked a bit silly to have such a small-brimmed mens hat on a bulging John Belushi, but it also reminded audiences of a time when men's style was more formal and they finished their look with a top hat, Panama hat, or some other stylish topper. In more recent years, Justin Timberlake has brought trilby back as have Madonna and Victoria Beckham.

Now that you have a better grasp of the ongoing fedora vs trilby debate, it's time for you to make up your own mind. If there's one rule to remember, it's this: A hat's brim should be in proportion to your shoulders.

As their name would suggest, trucker hats became a thing because of truckers. The baseball-like caps, with their mesh backs and foam fronts and emblazoned with a company logo, were popular as promotional items in rural American businesses , which would give them away to the truckers who passed through.

Unfortunately for us, the archetypes of masculinity in the early s were people like the lovably scummy Ashton Kutcher and Kevin Federline.

But what replaced the trucker hat was possibly even more sinister. Fedora-like hats in the early 20th century were often worn by both sexes. You can pretty much blame Justin Timberlake for the comeback of the mids. Even though all he was trying to do was bring sexy back, instead he ended up bringing back the sartorial equivalent of Pepe the frog.

All three of our menswear experts agreed that the fedora, despite being a classic, holds terrible connotations. But why? DeLeon says because the fedora is such a classic, men wear it expecting to appear gentlemanly.

Justin Timberlake, Ne-Yo, and Johnny Depp, all of whom were popular in the mids, were all channeling the old-school dapper aesthetic to some degree, but it was also simply a dark time for menswear in general. But as Schlossman argues, prioritizing form over function is basically the entirety of what fashion is.

Looking cool is more important to a lot of people, myself included, than necessarily being warm. Though the beanie has been somewhat of the scumbag hat of the past decade, there have been two sharply distinct ways of wearing it: sagging off the back, or rolled up tight.

It resembles more of a yarmulke than something else. You can buy a fluorescent yellow or orange Carhartt beanie for 30 bucks, maybe even less.