How To Wear A Fedora Without Looking Like A Creep

Is there an article of classic menswear more polarizing than a fedora?

Even the word “fedora” can sound a little cringey given the hat’s association with incel, neckbeard weirdos. Didn’t we all know a guy in college whom that perfectly describes?

Despite the hat’s less-than-favorable connotations, many of us like the way fedoras look and enjoy wearing them.

We have no illusions that we look like Harrison Ford or Dean Martin, though. We mostly just like classic menswear and the fedora is part of that, just like an overcoat or a necktie.

But unlike coats and ties, fedoras are much more “of an era” since their popularity declined sharply in the mid-twentieth century. There’s really nothing as obviously classic as a fedora in a modern man’s wardrobe (a bow-tie, maybe?) and because of that, wearing a fedora tends to be viewed as a bit anachronistic. A little costume-y.

So, for those of us who like fedoras, how should we go about wearing them without looking like creeps? How do we wear them without being associated with those insufferable “M’lady” types? How do we wear them without looking like we’re playing dress-up?

Now, when I say “fedora”, I am talking about “dress hats”… brimmed, felt hats that are/were typically worn to top off a suit or sport coat. I’m not talking about more casual brimmed hats, like western hats.

Most of you are aware that I have always been into hats. Ever since I was a little kid, I loved wearing hats. That’s probably because my dad always wore a tweed cap and I thought it was the coolest thing.

So, when I got into menswear, I naturally gravitated toward wearing all kinds of classic hats. The first proper felt hat I bought was a grey, Stetson Temple fedora, which I still wear regularly.

When it comes to wearing a fedora, in my opinion, one of the biggest things to keep in mind is to make sure it “makes sense”. What do I mean by that?

Usually, when men wear a fedora badly, it’s because of three main things.

One, they wear a cheap piece of junk. Two, they wear it in the wrong weather. And three, they wear it with the wrong clothes.

Let’s tackle these three points one-by-one…

When you opt to wear a fedora, it needs to be of decent quality and have proper dimensions. That cotton/polyester trilby from Walmart with the one-inch brim is not going to cut it. You wouldn’t wear an obviously cheap suit would you? No. Then why would you wear an obviously cheap hat?

A quality fedora will be 100% fur felt. That felt can be beaver (which is expensive), rabbit, hare, or a combination of those. Stay away from wool felt fedoras as they look cheap. A good hat will be at least $150. Yes, that’s a little expensive, but there are times when the expense it worth it. Companies like Stetson, Akubra, Selentino, and Borsalino all make fine hats.

The reason you want a quality hat is because you want to look intentional with your hat. Junky hats are not intentional. Handsome, durable, dependable hats in a timeless style are intentional.

Now, I mentioned dimensions before. It’s important to get a hat with proper dimensions if you don’t want to look like a creep while wearing it. By “proper dimensions” I mostly mean a brim that can protect you from the rain and snow. Because a fedora, before everything else, is a piece of outerwear. It needs to be practical. If you buy one of those aforementioned department store trilbies, it’s obvious you’re wearing it simply as an affectation, not because you actually need it to protect you.

That brings me to the second point. Often when I see a guy wearing a fedora badly, it’s because he is wearing it in the wrong weather. Like I said, a fedora is a piece of outerwear. I wouldn’t wear an overcoat or trench on a mild, sunny day. I wouldn’t need to. Same goes for a fedora. Now, you can argue that if it’s sunny, the fedora can be worn to keep the sun from beating down on your face or neck. That’s true, but remember, we are talking about fur felt dress fedoras here. In weather like that, if it’s truly hot, I would wear something like a straw Panama hat or a more casual western hat.

Wearing a fur felt dress fedora in weather that doesn’t call for it just looks off. On the other hand, wearing a fedora on a cold, drizzly day with a trench coat and a scarf looks perfectly normal because it’s obvious you’re wearing it practically. The hat is serving a purpose instead of just being a fashion statement.

Finally, and probably most importantly, one cannot wear a fedora well unless the rest of the outfit aligns with it. By far the biggest reason so many men look goofy in fedoras is because they are wearing them with incongruous clothing like hoodies or sneakers.

It’s called a “dress hat” for a reason. It looks best with a suit or sport coat. At the very least it needs a collared shirt and leather footwear.

Some men think they can’t “pull off” fedoras because they’ve only tried wearing them with casual clothes. No wonder they don’t feel comfortable in their fedoras! That’s like saying you can’t “pull off” black dress shoes because you’ve only tried wearing them with shorts and a tank-top.

When it comes to wearing a fedora and NOT looking like a creep, keep in mind that wearing one, unlike other items in our wardrobe (even the formal ones) is a choice. No one mandates the wearing of fedoras like they do the wearing of suits. If you’re wearing a suit, people may look at you and think “Oh, he’s on his way to work” or “He must have an important meeting today” or “He looks like he’s going out to dinner” and then not give it a second thought.

Wearing a fedora is different. If you’re wearing a fedora, it was a conscious choice. Because of that, you need to make sure that it “makes sense”. The “making sense” is what’s going to keep it (hopefully) from looking off or costume-y.

Like all clothing, fedoras only look good when there is a bit of authenticity. A cheap fedora worn inside with a t-shirt? Not authentic. A nice fedora worn with a coat and tie on a blustery day? Authentic.

I say this all the time, but always remember that clothes are the tools that accompany us on the adventures of life. They are not the adventures, themselves. The wearing of a fedora is a perfect illustration of that. Yes, fedoras are cool, but if you wear them in the wrong context just because you think they’re cool, you’re going to look like a weirdo. Wear a fedora because you need to, just like you would an overcoat.

You wear outerwear to protect you as you get to where you’re going. You don’t just sit in the house with it on because you like it (I mean, you could but that would be strange).

This all might seem a little unfair. After all, why should we attach all these rules to the wearing of fedoras? Can’t we just wear them whenever we want? We can do that with suits and stuff, so why not fedoras?

Well, like I’ve said before, clothing is a language and we need to speak the language that exists not the language we hope it will evolve into someday. At present, fedoras are sometimes viewed as silly affectations so we need to be mindful of what we’re “saying” to the world when we put them on.

One last thing about fedoras. A big incentive to wear them only in the proper contexts, as I have just laid out above, is because fedoras, when worn badly, are extremely repellant to women. Unlike suits, that naturally convey generally positive things like status, we are swimming against the tide of negative connotations when it comes to fedoras.

So, make sure when you wear your fedora, you follow my guidance and you’ll hopefully look more like Clark Gable…

…than this guy.