First off, let me get this out of the way: I am a HUGE fan of AMC’s Mad Men. I’ve watched the entire television series multiple times. Like many of my generation, it’s part of why I fell in love with men’s vintage aesthetic. There’s a reason classics never go out of style and this show is a great demonstration.

I’m turning 35 this year and I’m reaching a point in my life where I am ready to mature my fashion sense. Everyone has their own style and the look I’m building is something I call ‘modern vintage’. It’s been a slow transition but I reached the point where I’m ready to put the cherry on top of the sundae, so to speak.

So I bought a Fedora.

I was a bit hesitant when I ordered it online. I wasn’t sure how it would look without tying it on, but lately the hat style itself has been getting a bad rap.

This wasn’t always the case. Back in the early 20th century the hat was a staple of men’s fashion. Men would rarely be found in public without any type of hat, but the fedora was by far the most popular.

Then end of the 1960s saw certain items of men’s fashion disappear. While some of them have made a come back the fedora hasn’t been able to reach the peak popularity it once had. That is, unless you count a certain demographic.

PAIN IN THE NECK

In the late 2000s a new trend began to emerge. A particular stereotype of young men had become a meme spread around the internet, known as “neckbeards.” If you’re familiar with this group of people the name alone is enough to make you cringe.

Characterized as obsessive men who inhabit their parents basement, they are often stereotyped as overweight and having unkempt facial hair (hence the name).

M’lady

With an affinity towards anime and swords, a common theme associated with this type is a false sense of superior intelligence. These poor souls are also known to be socially awkward, assigning themselves with the nice guy syndrome. You can find them online writing diatribes of the dreaded ‘friend zone’ and lamenting that all women only want to date assholes.

Obviously this is a label most young men do not want to be associated with.

But one fact that has been so deeply ingrained with this stereotype is that they all prefer to wear fedoras. It’s become synonymous with the character set. It’s the first image most people see in their mind when they hear the word.

Although technically they are wrong. The hat worn the most by those considered neckbeards is actually called a trilby. Similar to a fedora, it generally has a stingy brim and shorter crown.

A fedora generally has a brim of 2.5 inches or more, while a trilby will have 2 inches or less. The wearer also has the option to flip or “snap” the brim of a fedora up in back. On the other hand, a trilby will usually be sold with the back brim already snapped up.

The general public isn’t discerning enough to tell the difference so people started referring to all hats worn by this group as fedoras. The line between the two can get very blurry, but you’ll know the difference when you see it.

NAVIGATING ROUGH WATERS

If you’re like me then you refuse to let this classic piece of men’s headware die in the gutter of fashion faux pas. To set yourself apart from the stigma surrounding the fedora there are some rules you need to keep in mind.

Treat the hat and yourself with respect. You have to approach it similar to any other article of clothing. Like a good suit, the fit is crucial.

Sadly, this part is often overlooked.

A fedora should fit snug on your head to keep it from blowing off, but never small enough that you have to yank it down. When resting, the brim should stop 1–2 fingers above your ears. If it’s resting on your ears you can either go a size down or purchase hat sizers to tighten the fit.

Always make sure to consider the brim length. Choosing an incorrect size for your face shape can exaggerate the wrong features. There are plenty of resources online to help you choose the right fit — use them!

Another trend I noticed is young men wearing ‘fashion’ hats. That is, hats with patterns or designs screen printed on them. If you buy a hat from Hot Topic chances are it will have pinstripes or four aces painted on the side. This comes across as cheap and costumey.

*shudder*

A good rule of thumb is to think about it’s practicality. Buying a fedora in a neutral color like gray or brown will enable you to pair it with many outfits. The right fedora should blend easily and become part of your whole ensemble.

A great piece of advice I use when it comes to headwear is this: use it as a condiment, not an entrée. A hat is suppose to help compliment your outfit, not draw attention away from it.

So often do I see young men of this subset pairing a trilby with a t-shirt and shorts. This look screams immaturity.

Think about the type of outfits men wore when the hat was in fashion. Use that image to help create your own look and the fedora will fit like the last piece of a puzzle.

This guy gets it.

Remember: a fedora is not a catch-all. You wouldn’t wear a baseball cap to a wedding, would you? Keep the fedora for appropriate occasions.

FEATHER IN YOUR CAP

The general attitude I get from these ill-fated attempts is the wearer assumes the hat will make them seem more mysterious. I hate to break it to you, but that is not the case.

Coordinating a clean, timeless look will only help build your confidence. A fedora should help exhume that confidence, not hide parts of your personality.