Is "Fedora" Still a 4-Letter Word?

Photo from Stoffa

Man, brimmed hats sure have taken a beating in the last century. Once virtually a prerequisite for being a grown-up, the latter half of the 20th century saw the fedora and and similar headwear (the trilby, bowler, homburg, porkpie, etc.) move so far down the ladder of sartorial necessities they became an afterthought in most men's wardrobes - and then not even. Worse, as young men growing up in the 1990s-2000s felt the need to dress better but didn't know how to go about it, they reached out into the void for something "classy," and Satan reached back and handed them a cheap fedora or trilby. Between the neckbeards trying/failing to look like Indiana Jones, the vested and clip-on suspendered bartenders, and the Backstreet Boys, it's hard to imagine another article of clothing that's become so reflexively reviled in the collective style consciousness.

Tell me why.

It's a real shame, though you could say it's also just a sign of the times. As formality and tailored clothing have continued to decline, passing a man on the street with a suit and brimmed hat has become somewhat of a rarity - at least here in the US. If you can recall any of those times, how many of them were older men (probably most)? And if you came across a younger man wearing a similar outfit, did it seem natural (probably not)? The kindest reason is that it's just not a common sight, so even if everything is right it still tends to draw a more skeptical eye than wearing a baseball cap or a beanie. But as you might expect, younger guys are usually not as comfortable or mature in their own style, so when wearing an item that has such a low threshold for affectation, any little thing drags it across the line. Looking comfortable with a more difficult style item can be a tough ask, as you need to have the confidence to wear something that's serves as a visual homing beacon for most people. This beacon often transmits the message "I'm a huge douchebag."

Photo from Lock & Co Hatters

But it's not enough just to have confidence; you also have to pull off the look itself. So how do we successfully marry such classic style with modern sensibilities? Brimmed hats can be pretty hard to pull off naturally in the more formal areas of dress, but the casual end of the spectrum is a little more forgiving. I particularly like the more unstructured fedoras and trilbies that pair well with a more rugged and rumpled wardrobe. Put This On has a nice article about straw hats being the easiest of the traditionally styled hats to pull off, but something like a packable felt fedora or trilby can work well in the cooler months for everything from casualwear to casual tailoring, especially if chosen in a neutral shade. It can be crushed, rolled up into a pocket, and abused with wanton abandon, which - like a lot of other things I enjoy - makes it only look better. Lately I've been seeing them used successfully with a lot of workwear, which is probably in most guys' wheelhouses and the safest way to approach the look from a casual perspective.

Fits from Whaley's World

It also helps to have some age or character to your face, which is why older guys and men with certain styles of facial hair (*NOT neckbeards*) tend to look good with hats. How old is old enough? It's hard to say, but when you start making bad puns and dad jokes you're probably in the ballpark. If you're baby-faced (like me) and/or follicly-challenged (also like me), a good non-dorky pair of glasses can also help anchor the look while adding some character. A good real life example is Dennyspirit's Instagram account, who you'll find often wearing a Stetson hat with his enviable RRL collection in a way that seems entirely organic and unfussy.

Fits from Dennyspirit

Brimmed hats run a wide range of prices, but they don't have to be that expensive. You can find quality vintage examples on eBay for reasonable prices, especially if you have a smaller head, or just wait on some sales from a place like Mr. Porter, No Man Walks Alone, End, etc. if you're savvy. Lock & Co Hatters, Stetson, and Stoffa all make attractive options. I recently picked up a rollable wool felt trilby from Lock & Co named The Rambler for about $50 that I've seen featured around the net. You can find some decent wool pieces from some of the more budget-minded companies out there as well if you don't want to drop hundreds on a fur felt model at an apex level company like Optimo.

Fits from Crafted Paris

If you're at the stages of styling where the sort of questions you ask are "what color shoes go with this suit," this might not be something you want to take on right now. Yes, it could look good, but it's the sort of thing that has the potential to turn an otherwise invisibly mediocre outfit into something that makes people around you want to slap you. But if you're in the process of exploring and developing a more expressive personal style, a good brimmed hat could really cap off a great look.

Pun game on fire.