So, when my Dad was my age (early 40's), and I was a teenager, he'd embarrass the heck out of me by wearing a pith helmet while mowing the front lawn. Yes. A pith helmet. He had it left over from when he was in the Air Force. Not that they issued it to him. He just had it from back then.
He'd fire up our nasty, smoky old lawn mower and grudgingly hit the green. I inherited my loathing for yard work from my Dad. Not gardening; gardening is a lovely pass time. But the care, feeding, watering, cutting, raking, etc. of a patch of crappy, homogeneous weeds is truly noxious to me. If it was culturally OK to have a sand/rock garden in one's front lawn in Ohio, I'd do it.
Out Dad goes! Wearing the pith helmet; a short-sleeved, white, button-down shirt; plaid Bermuda shorts; dark socks; and sandals. You can imagine that I was somewhat... chagrined.
Until I got to be about...well, my age now. A few years back, I took to wearing a Tilly hat (see pic) because we found one that fit my great, huge noggin'. It keeps off the rain, the snow, and the sun. It floats. It has a secret inside pocket. It has a drawstring inside that can be worn three different ways. It is an awesome hat.
And, last summer, I went out wearing that hat, and a pair of cut-off sweats, and dark socks with sandals (cause the sandals chafe, but I didn't have [couldn't find] any clean white socks, and I had a window-of-opportunity of 30 minutes to mow before the rain was going to hit) and began to mow.
And then realized I'd become my dad. Cursing while mowing the lawn, wearing a dumb-ass hat. And it occurred to me why men of a certain age and type -- men like my dad, and now me -- wear dumb-ass hats: because we like them, and don't give a crap what other people think anymore.
God bless the moon, god bless me, and god bless my dad. Who taught me, silently (except for the cursing) to be myself.
[Note: I'm posting this in the winter because I feel like it, dammit!]