I guess if you can pull one off, go for it! Wouldn't blink twice at an older guy wearing one.

I sure couldn't pull one off, that's for sure.

I guess my disdain for them stems to some people wearing them during college who I didn't enjoy very much, so my view may be a bit slanted.

The hat subject has been covered before, and I will again say I am not a fan of ball caps. Hats are made for a reason, and it seems to me most are not used for a purpose, especially ball caps. Ball caps were made for baseball players, and are part of the uniform. I don't know when it morphed from purpose to fashion statement, but I just don't care for it. I really dislike when a person is wearing one in a restaurant, there's no need for it.
If you're using one to hide your head, lose it. You're not fooling anyone!

I will wear a cap when I have need to; out in the sun for long periods, yard work, ball game (where they most belong), beach, Disney, zoo, etc. You get the picture.

Didn't really wear hats until I joined the Air Force.  Learned the hard way that they weren't just for on duty when I was stationed at Nellis AFB NV, right next to Las Vegas. 

I like boonie or bucket hats the best for knocking around in the summer.  If I wear a baseball hat, you can be darned sure I'll burn my ears.  In the fall I switch to either a fedora (I'm from Chicago originally, what can I say?) or an Irish Driving Cap.  In the winter I wear a watch cap or my http://www.stormykromer.com/.

Next I want to get a right proper Derby.