Help with styling a fedora or trilby

[Crazy8]

I'd love to wear a fedora or trilby but need help with what to wear with one. I'm scared of looking silly. Any ideas?

I keep trying them on as I like the idea of them, but the minute I do I feel like I'm playing dress up!

I do love my panama on holiday though..

Sorry, not helpful I admit

I just bought one, so I'm still playing about with styling it.

It looks rubbish with my parka, that much I do know!

Maybe I just need a whole new wardrobe to make the hat work!

Try typing "fedora hat outfit" into Google images and see what you like the look of. Thinking of getting one myself. I bought a bowler hat last year (when they were everywhere) and wore it more than I expected.

Thanks. Will do.

Just wear it with anything to start. A Fedora is quite a big hat and will take some getting used to if you don't normally wear hats.
I wear a fedora and a trilby, usually when it's drizzly. The trilby stays on in the wind but the fedora is a liability.
The more you wear them the more you will want to wear them.

Don't pair it with hiker style stuff like parkas. (I know parkas had a fashion moment but I cannot combine them successfully with hats.) Because it's menswear, add in some menswear touches like brogues or desert boots. Try an easy combo like boyfriend jeans, a trench and a sweatshirt or a blazer. Some crisp tailoring always works with hats. If you do skinnies, a loose top and a huge scarf with a trilby, it can be a top heavy look, so you'll have to think about footwear to balance it out. If you are still experimenting, avoid scarves or accessories to start with, less is more. Is your hair right for a hat? Is the color right? Dark gray is more flattering on me than black. If your head is quite large, hats may be too much.

I'm a big hat wearer - trilbys, fedoras, panamas, cloches, newsboy caps...

Yes, it just looked ridiculous with the parka!

But it worked well with a long tailored coat and scarf, and also with a chunky jumper and skinnies/OTK boots. My fedora is black, but I do suit strong colours.

I've had years of hating hats, mainly because my hair was always wrong, but I've been growing it for a couple of years and have "hat hair" at last!