The 'loose' look.

[Jeff M]

..... so the hat doesn't look stupid.
...

And that is the key point.
It either looks stupid (see Kid Rock) or it doesn't (Johnny Depp.)

 

[danofarlington]

And that is the key point.
It either looks stupid (see Kid Rock) or it doesn't (Johnny Depp.)

That's what is interesting. One guy's stupid is someone else's cool. I wouldn't wear my hat like Kid Rock--geezers aren't allowed--but others might. How you use your hat is a very individual thing. Personally I like to see all the ways that people use their hats. As long as you "own" the look, or look like you "own" the look, and it's not too stupid, then you can do it. I can get Kid Rock's style. Johnny Depp's style is more traditional. But the more different styles you see out there, the more space I feel to shape up my own style, and not feel like I'm wearing an "everybody hat" like in the 40s and 50s.

 

[59Lark]

what look are you trying to achieve.

IF its a goofy look, go ahead, i went from seven and five eights to a seven and three quarter due to my head getting fattter. Fat head jokes aside, I also find my hats quite often get wet and shrink and a little bigger is safer but again they have to fit so they dont blow off. I always remember having a grey fedora blow off and rolll under a parked oldsmobile and it leaked engine oil and some got on my fedora. Unless you have as much hair as johnny depp to conpensate try a different hat for a different look not a drippy, droopy or slippy fedora but last but not least. this is only my humble opinion due what you want and reap the rewards or the results. 59 Lark, the other lark the one named after a fine automobile and which some ended up in austraila . fftopic:

 

[Jeff M]

The real question here should be, "should I wear a hat that makes me look like a doofus..or not?" I'd recommend against the "doofus" look, myself.

An oversized (definition varying) hat may look great on some folks, idiotic on others.
Just need to find out what it looks like on you.

 

[Pompidou]

The way I see it, one doesn't wear a hat these days to blend in with the crowd. If you get an inch of an idea, run a mile with it. What's the worst that'll happen? Someone will snidely comment, "Nice hat..."? You'd get that wearing a suit and a homburg. Since being conservative doesn't stop the heckling, it's silly to let public opinion dictate your style in hats. The only rule these days is, "Do what you want". All that really matters is that you're you. People can spot me a half mile away. I love it. Wear your hat oversized if that's what you want. You'll just get Kid Rock comments instead of Indy Jones. Not a deal-breaker in my book.

 

[Big_e]

I must have an exact fit on my fedoras, boaters and any brimmed hat for that matter. A loose fitting hat makes it easy for the wind to take with it. I will tolerate a loose fit with clothe or wool newsboy caps.
Ernest

 

[danofarlington]

The real question here should be, "should I wear a hat that makes me look like a doofus..or not?" I'd recommend against the "doofus" look, myself.

An oversized (definition varying) hat may look great on some folks, idiotic on others.
Just need to find out what it looks like on you.

I agree 100% that that's a ground rule.

 

[Havana]

If an informal look is what you're really after, I suggest getting the right fit and then work with the crown and brim. Just poke some casual dents in the crown. If you put the hat on about 1 inch off center, you'll get a nice asymetrical wave in the brim. That should give you a proper "gentleman of the road" look.

 

[Big_e]

Just as Havana said above. Start with a proper fitting hat. Turn the front brim up. In early days that was the "goofy" or humorous look. Later it became the informal, casual look which gives the appearance of a hard worker, heavy thinker, possible thug or someone who cares to wear a hat, but too distracted to bash it properly.
Ernest