Every day someone walks into our shop, and says they "don't look good in hats". It's like saying you don't look good in shoes, it really depends on the shoes. Then I take them through the process of finding the right hat and show them how to solve this puzzle. Often people are overwhelmed with joy, that for the first time in their life they actually look amazing in a hat.
I remember one man in his forties whose wife was cajoling him into getting a nice hat. We talked for a while, and he explained that he always felt embarrassed wearing hats, so he never did. Consequently, he had just had his third series of cancers removed from his head and ears, and his family was worried for him. We took our time and found the right hat. When he left with a hat on his head, he shook my hand with tears in his eyes and thanked me.
At some time in everyone's life (often childhood) they have bought a hat, and been teased or ridiculed for the choice. Often this experience lingers, and every time they put on a hat, all they see are the things that are wrong with them. Self-judgement can be cruel.
The truth isn't that they don't look good in hats, it's that they are wearing the wrong hat. Picking up a hat from a pharmacy or convenience store is like buying a 3-piece suit from a gas station. It is extremely unlikely to work out well.
Hats are perched on top of your head, so they are incredibly obvious in much the same way as glasses. If they are poorly fitted, cheaply made or badly chosen, it is yelled across the room to everyone that sees you. In the old days, you always bought the best hat you could afford because it was your most important piece of clothing.
We now live in a disposable world, where everything is cheap. But with hats, you get what you pay for. There are no short-cuts and sometimes you need a guiding hand.
The best way to look good in a hat is to buy a good hat - it's that simple. What you are buying is the expertise and knowledge of the designer and the craftsmanship of the construction.
Another way to solve the problem is to talk to a real hatmaker. Seeing your face, and exploring the possibilities works out a whole lot of issues in a very short time. Unfortunately, good hatmakers are rare, and the likelihood of you finding one in your area is ridiculously small. A professional online fitting is a great alternative, particularly if you feel a little unsure or previously traumatised by hat criticism. If you can't do that, then send me a photo and I will help you out.
The thing that people usually get stuck on is finding the right hat for their face. It can seem daunting, but it is relatively simple. Your hat needs to mirror the shape of your jaw. If you have a big square jaw, get a square crowned hat. If you get a pointy one, it will look ridiculous. In the same way, if you have a weak jaw, you get a soft tapered crown. If you are really big, get a bigger brim.
What if you have a weird head? Working with heads every day, you soon work out that most people do. Everyone thinks there is something wrong with their head.
I am a hat evangelist because I know the impact a good hat has on peoples lives. It is the most practical of tools, that brings more positive attention than a Ferrari, boob-job or celebrity. When you get it right, life feels better.