Question about hat style.

[SLOshank]

Flat cap is the actual answer here.

It won’t bow off in high winds downtown.
You can stick it in a pocket when you go inside.
Dresses down well for casual after work.
Will keep your head warm, can get models that will cover your ears too.

You're right. Extremely practical. I've worn a 8 panel newsboy cap with a suit in the past. I don't think caps look good with suits in general, but they are acceptable and extremely practical.

 

[SLOshank]

If money is no object, go get yourself set up at Optimo, they'll help you choose a hat to suit your face and the Chicago weather.

If on the other hand, you don't feel like dropping $1k+ plus on a hat, check out Akubra hats. They're obviously not quite as finely appointed as a luxury Optimo, but for >$175, they're a great value and very resilient. A popular choice around here is the Fed 4 and another is the Campdraft. The latter is more or less a vintage styled Open Road (Akubra once held the Stetson license in Australia).

I already wear Campdrafts with jeans and such. But with s suit? In today's world? Would it really work without looking odd?

 

[jlee562]

I already wear Campdrafts with jeans and such. But with s suit? In today's world? Would it really work without looking odd?

Sure, why not? It's a semi-dress hat (for the purposes of this discussion, a Campdraft is basically an OR).


I mean, maybe you don't want to take fashion advice from a guy who prefers not to wear suits, but I've done it. Probably not the best with a black suit, but I thought this look was good enough for a wedding (and my brother and sister-in-law didn't complain). YMMV ¯\_(ツ)_/¯



Otherwise I'd suggest at least a 2 3/8" brim, unless you want the Mad Men look.

 

[Rmccamey]

Smashing...or, perhaps, dashing! Very nice look, indeed.

Sure, why not? It's a semi-dress hat (for the purposes of this discussion, a Campdraft is basically an OR).


I mean, maybe you don't want to take fashion advice from a guy who prefers not to wear suits, but I've done it. Probably not the best with a black suit, but I thought this look was good enough for a wedding (and my brother and sister-in-law didn't complain). YMMV ¯\_(ツ)_/¯



Otherwise I'd suggest at least a 2 3/8" brim, unless you want the Mad Men look.

 

[GHT]

Fabio is definitely Mr. Stylemaster!

Absolutely! My wife would be a lot more supportive of my hat collecting if it made me look more like him.
He also shows how versatile hats can be as his collection isn’t huge but he always looks great and has the right hat to complement his ensemble.

If I looked more like him my wife would not recognize me!

Neither would mine, but I don’t think she’d mind.