But What If My Head Gets Cold?

I find myself between a rock and a hard place.

You see, I want a hat.  Not just any hat, I have hats, but a fedora.  Not a standard fedora with a wide brim and whatnot, but a Neal Caffrey from White Collar sort of fedora, also know as a trilby hat.  This is probably the best hat in the world, with exception given to the Indiana Jones fedora (which I wouldn't look great in walking down the street), and it fits my head well.  However, if you've seen White Collar, you'll notice two things:

1. Neal Caffrey is incredibly more handsome than myself.
2. When Neal wears his trilby, he is also wearing a particularly snazzy suit.

 

Now I've tried on a trilby practically every time that I've been to Target in the last four months or so, including whilst gift shopping for Christmas, and have come upon a different idea every time.  I've found that the hat can look quite dashing when I am wearing a long sleeved, button-up shirt (with jeans or slacks); I've also discovered that the hat looks like utter rubbish with a long sleeved, casual T-shirt; and yet, the hat does go rather well with a (short sleeved) graphic tee and jeans.  I'm not even going to go into how I look in a suit, even without the hat.  I become Chris Farley stuffed into David Spades coat when I where suits.  Seriously, my wedding pics don't lie.

See? Decent, if only slightly chubby.

My dilemma is this:  I want the hat, because it goes well with my work clothes so I can wear it into work Dick Van Dyke or Mad Men style; or out on the town with a nice or casual shirt.  But, my wife has seen the hat on me when I am wearing a sweater or other casual long sleeved T-shirt many times, whereas she has only seen it on me, in a positive light, once.

So, because I value Alex's opinion, I haven't bought the hat, but I believe that I could potentially get a lot of use out of it, without looking like a complete douche-canoe.  So far, she says "No."

Thoughts?

I'm not really sure about this one...

"A picture may be worth a thousand words, but it only takes a woman's "Ugh" to send a man's pride down the toilet."

~Nathan Culley