Hats

**gkk** · 12-10-2011

As a non-grandfather who regularly wears a fedora, I can tell you that if you wear it while thinking you look like a dork, you will look like a dork. (Also if you wear it with a button-down or T-shirt and jeans.)

If you can wear it long enough to get past that and start wearing it unselfconsciously, the practical benefits you already noted in the OP are real. Also, it gives you incentive to dress more grown-up-like. If you stick with it for a while and still feel like everyone is looking at you as a debonair sysadmin, then, well, at least you tried.

For the same reason, +1 on starting with a "stingy" brimmed hat, though going more Stetson sure keeps off the rain a lot better.

/gkk

**caleb** · 12-12-2011

Originally Posted by Ben

I'm not wearing a knit cap with a suit and tie

If it's cold out and you're wearing an overcoat, I'd say you'll look funny without a knit cap on.

Match one of these caps from JPress to your overcoat or scarf and you won't be in danger of sporting any ridiculous earmuffs.

Do:

Don't:

**lavi** · 12-12-2011

I have a dark grey Brook Bros wool fine knit hat. Don't remember where/when I got it. It's nice. I wear it with everything from North Face to my Pea Coat.

My dad wore and could successfully pull off a Greek Fisherman's hat (not him in the pic).

Or just go with the Italian Racing hat (Gatsby). Yes, that's me minus my beard.

**Ben** · 12-12-2011

I have no idea how I missed all of the utterly useful replies to my thread over the last few days. Mea culpa.

I think I'm just going to have to go GKK's suggested route. Wear the damned brimmed hat and pretend I look awesome. To be clear, I'm primarily talking about something to wear with a suit and overcoat, so any kind of knit hat would look a little silly, IMO. And the flat/newsboy/driving caps all remind me of the soccer players from my high school. There's nothing worse than a soccer player.

**christian** · 12-12-2011

There's a lacrosse player. But seriously, good call on the hat. It'll look fine with a proper outfit.

**Ben** · 12-12-2011

We don't have lacrosse in public schools in Tennessee. So the soccer teams have to absorb all the douches who would play soccer AND lacrosse up north.