Men who wear trilby hats...?

[GeeWhiz]

I'm a man who wears a trilby hat whenever outside (not always), especially when it's sunny or windy (sensitive eyes and long hair...). But I notice I get stared at quite a bit mainly by women. Do they think I'm the neighbourhood's undertaker or the vampire from next door?

I appreciate it's a silly and shallow thing to ask, but... why the stares?

Are you sure it's the trilby? It probably isn't. And are they stares? Not just looks?

Maybe they like your hat?

Trilby's remind me of 1980s pimps

@anotherchange111
This one...

I've got a collection though

@wizzywig LOL

@Smeaton ha ha

I'm in my early 30s

I'd groan a little and think 'hipster'.

@Smeaton I almost spilled my coffee...haha
I do wear formal clothes though. No glasses.

my dad wears a trilby he was born in 1930 so can get away with it

Fedoras seem popular with the sort of men who have read The Game and do creepy rehearsed chat up lines on women.

So they may be eyeing you warily expecting you are about to neg them

Hat and long hair is a less usual look- people normally notice things that are different to the norm.

@MojoMoon don't even know what The Game is

@OutandIntoday Possibly.

without seeing a photo of the overall styling of your trilby with hair and clothing, its really hard to say. i agree that hat and long hair is a less common look and im not sure what you mean by formal clothing - for work or weekend wear or both??

My almost 4 year old ds is hat mad and has a checked trilby and always wants to wear it with an outfit that totally doesn't go.. can never be persuaded otherwise, he does get some odd looks!
I'm sure folk are just admiring yours, it looks quite smart?

@redmarkone Mostly shirts, chino or dark jeans, and a dark suit/smart jacket. I guess sorta smart-casual. And yes, I used to wear a suit for work, which got me into the habit of dressing smart-ish outside work.

chinos

Something like that -ish

My son is 10 and has a huge collection of hats. Everything from bowler hats to fedoras and flat caps. He looks fab, I couldnt ever imagine him not going out without a hat.

You need the whole outfit though. Chinos with shirt and waistcoat and blazer jacket type outfit and smart tailored suits. Wearing sweatshirt and jeans would look odd with a hat.

It really depends on the overall look and whether it makes sense to the eye.
Trilby hat can with short hair and relatively smart can mean a reference to old school gent. Then there’s trilby as a hipster look. Trilby as an rocket/musician look. Then (sorry) there can be trilby as a creepy look. It’s not the trilby itself but his well the overall look works and whether you pull it off or not.

This takes time to figure out - probably a second, or a glance rather than the usual nano millisecond someone not wearing anything different or eye-catching gets.

The pic above of Man in trilby looks good. He has reference start dress and has short hair though, so it’s modern take on classical gentleman dressing. I don’t know how long hair fits in without maybe you looking like a musician which is definitely more eye catching/unusual ,for better or worse.

*referenced smart

People generally don't wear hats on a day to day basis. They haven't since the 60s. People are looking at the hat because you don't see them very often.

Tbh, I'm not convinced on the long hair/hat combo. I'd go for one or the other.