Hats

I'll get straight to the point: Can I pull this off? If so, what could I possibly wear with it? Even if your answer to #1 is no, humor me and answer #2 anyway.

For your reference, here's a picture of the hat in question:


...and here's a picture of me, already looking stylin':

Spoiler Alert, click show to read: 

Much appreciated!

definitely.

You be needing a pimp cane.

IMO, you may be able to, but would need to see mannerisms etc. but i'm that picky.

Black jacket, black shirt, red tie, red pants, black belt, black shoes. Or Black jacket, red shirt, black tie, black pants, red belt, black shoes.

Halloween?

Originally Posted by Psychonaut

Black jacket, black shirt, red tie, red pants, black belt, black shoes. Or Black jacket, red shirt, black tie, black pants, red belt, black shoes.

Halloween?

I have a blood-red shirt and tie, but that might not be a good enough match.

And no, not Halloween, just to have.

Brilliant Nobody wears real hats anymore, it's all caps nowadays. I think a hat like that needs a pinstripe suit.

Here's the same hat in blue. Try to find the corresponding outfit to match your red hat.

Spoiler Alert, click show to read: 

Originally Posted by GeneralHankerchief

I have a blood-red shirt and tie, but that might not be a good enough match.

And no, not Halloween, just to have.

You, sir, could pull off whatever you wish.


In all seriousness, yeah I think it would look okay.

Go for the brown or black one.

You'll make that hat look good, baby

Originally Posted by GeneralHankerchief

I'll get straight to the point: Can I pull this off? If so, what could I possibly wear with it? Even if your answer to #1 is no, humor me and answer #2 anyway.

For your reference, here's a picture of the hat in question:


...and here's a picture of me, already looking stylin':

Spoiler Alert, click show to read: 

Much appreciated!

All red. It must all be red. Everything, skin and all.

I'm not entirely sure what goes with red except red.

Can´t be done. I mean common

Okay, so ware the red hat and a lime green Hawaiian shirt and orange shorts...

Personality/demeanor affect the impact of wardrobe on those who observe. If you are going to wear something bold, for it to work, the way you carry yourself and interact should compliment what you wear. Is your personality/demeanor such that you can wear that hat and the bold clothing to go with it, without coming off as ostentatious?

Location/context is important. A red fedora screams "Notice Me!", so you don't want to hide in transportation; it demands a walk-about, and a confident, but distracted, cool demeanor - as if you hadn't noticed that you accidentally put the red one on today.

East Coast, Urban: viewers will assume you are "in sales"
Deep South: they'll assume you're a cocky Yankee, out to stir up trouble
West Texas: they'll wonder why your brim is so small
Minnesotans: might wonder why you're hunting off-season
Southern Californians: will assume you're an aspiring performer

I wonder how London, Paris, Berlin, Rome & Moscow might apprehend the sight. Or Peking.

The remainder of your wardrobe demands solid colours; shun earth-tones. Shoes, no boots.