Q&A for How to Wear a Fedora

There is no rule for dark colors for hats, so you can wear them all year long. Most people prefer darker colors in the colder months and lighter colors as it warms up, but there is really no hard and fast rule.

Wear black or darker jeans. This makes most outfits look less awkward, especially white.

Absolutely! There is no rule for how old you have to be to wear a fedora.

Well, there are more formal hats, like top hats, bowlers, and homburgs, but since they can be seen as old-fashioned, there is no problem wearing a fedora instead. All hat rules must be observed, though: You shouldn't wear it inside a building, especially if you're sitting at a table, tip it to salute people, and remove it when interacting with ladies. Never wear it inside a church, but do wear it in a synagogue.

If you normally dress up/wear clothes that are nice, then go ahead. But you shouldn’t wear it when it doesn’t fit with your outfit. It looks silly.

Yes, you can.

Fedoras can look stylish during any season. Just be sure the fabric you choose is the right weight (lighter weights for hotter months).

They might. Who cares? I am an older man (early 60s) and wear my walnut brown Stetson Stratoliner fedora every day. Several of the younger (20s and 30s) men and women in the office have commented on how good it looks.

It costs more than an actual felt fedora to clean one, decide if you really need to wash it or merely buy another felt fedora.

Let your fedora shape itself naturally. Just wear it appropriately and it will naturally shape itself to fit your style. If you want to force a shape, then do it gradually and with your hands; if you force the shape too quickly, it will be angular and blocky.

If it fits your head this way, why not? It will make you look like a 1930's gangster. Personally, I wear mine "level" and not canted, but it's your choice.

No. A fedora only works well with a dressy outfit. Shorts and a t-shirt won't go well with a fedora.

Those aren’t things you need to hide! Fedoras are a great accessory and can help with your confidence, but the only way to be truly confident is to love yourself.

I’ve just been in the UK and I wore a fedora constantly. As a teenager people often wonder why I would wear a fedora and I tell them I enjoy wearing it and I have been told they suit me so I just owned it. When I was in the UK I got lots of funny looks and I think it is because it is not a traditional English hat, just remember to own it.

The 90s grunge style is really good for teens, the 80s and 90s are making a comeback recently.