gangster with a fedora hat

Wearing a hat properly is like putting a cherry on top of a cake – it makes a bad situation bearable and a good situation even better. If the cake is awful, at least what you are left with at the end is that awesome sweet-sour cherry and if the cake is great, well…the cherry just enhances the experience. The same is with a hat; if your outfit isn’t that good, you can just put on a cool fedora and take the focus of the train wrack that’s happening bellow the neck. On the other hand, if you are stylish and well-dressed even from the neck down, this hat will only emphasize your overall good looks and style…but only if worn correctly.

First thing you have to know is that not everyone can wear a fedora hat. This has nothing to do with the hairstyle, financial status or even the way you dress. What separates someone who can wear a fedora from someone who can’t is the attitude. You might even say it’s all about the hattitude. The point is that you can’t let your hat wear you. People have to know who the boss is in this relationship between you and your hat. If you are having second thoughts about wearing the hat, if you are insecure and uncertain, don’t even put it on. To be able to pull off a fedora you have to be confident. You have to be sure that you are the boss; you have to show everybody that you own the hat and not the other way around, even though it might feel a bit weird at first. In order to overcome this stage, wear a fedora frequently regardless of what others say, and, in no time, the hat will become your signature and you will be comfortable with wearing it on a daily basis.

man wearing a fedora with pattern

In order to have the right attitude, you need to have the proper hat to support it. This means that not any old fedora will cut it. Actually, an old fedora left over from your father or even grandfather would be perfect because these hats tend to age well, just like Sean Connery, but only if the hat is well preserved. The problem occurs with brand new hats. Most of them lack in style and authenticity because, thanks to the 90's and a few boy bands, they’ve become pretty mainstream. With this came the mass production of the hat and everything that is mass produced lacks in flair and uniqueness. You can now buy a fedora in Hot Topic, walk out the store thinking that you’re cool and fashionable, and see ten people in that very mall wearing the identical hat. The best thing to do is to buy a real, 100% original, fur fedora. However, this may cost you a lot, so if you don’t have this kind of money, buy in bulks. Buy as many as you can for as low as you can, still minding the style and quality, so you can at least choose which one to wear every day.

To bring the best out of your new fedora you will have to know how to combine it with the rest of your attire. You can never go wrong if you combine it with formal clothes, i.e. suits. The most important thing here is to match the colors. You can either go for a perfect, almost identical, match (for example a navy blue suit with a midnight blue fedora), or you can choose to contrast these two (for instance a charcoal grey suit and a black fedora). You can even leave out the suit jacket, and put on a cool vest. For a more casual look, roll up the sleeves of your shirt. Combined with a hat, it will give you a manlier, working type, ragged look, whilst maintaining the fashionable appearance.

man wearing a suit and fedora combination

I’ve already mentioned that the boy-band era, (that is to say – the 90s), in a way ruined the fedora hat. The main reason is that they’ve started wearing it with almost anything: t-shirts with childish prints, shorts, sneakers, it doesn’t matter. Nevertheless, you should definitely avoid this. The biggest don’t of wearing a fedora is to wear it with casual clothes. Let me rephrase this: the biggest don’t of wearing a fedora is to wear it with distasteful clothes. You can wear one with a plain button-up shirt, casual long pants and casual, yet tasteful shoes, but the main rule is that you have to have a collar and your shirt has to be tucked in your pants.

Another thing that you have to look out for is not to buy a hat that looks good on the stand, but a fedora that looks good on you. The hat must fit the size and shape of your head. If it covers more than one third of your forehead you know that it’s too big (not to mention that it shouldn’t cover your eyes), and if the smallest breeze knocks it off your head you know it’s too small. If your head is long and thin, never buy a hat with a tall crown. Tall-crown hats elongate your head, so only people with short heads should buy them. Otherwise, you’ll just look like an alien trying to infiltrate our society.