I have a straw trilby also. A trilby is a narrow brimmed fedora as far as I can tell. I wore it a couple of times in the summer.
I’d wear a boater if I had a seersucker suit.
Just stuff something under the inside band. If you have a local store, they probably have a little rubbery band they will put in, but you can use most anything – just be aware that toilet paper works fine until it gets wet.
Well, that’s what I thought, and then I see something like this.
I love my flat cap, but it’s generally too damn hot here to wear it. The sweat stains look pretty ugly.
Well that looks like a regular old fedora. Trilby makes me think about the hats worn by Frank Sinatra and occasionally Bing Crosby instead of his usual full brimmed fedora. The straw version has that retro look that goes good with summer wear. The kind of thing I wear to the Yacht Club*.
*Excerpts from a review of this Yacht Club:
“It’s a dive bar. On the water. Cash only (with an ATM located on-site).”
“A limited greasy-spoon type menu, pool table, an old-school video game or two, and generous pour (my cup o’wine) added to the water view looking over to Waterman Grille, Stuck-up Bridge (aka: Crook Point Bascule Bridge), and India Point Park with plenty of outdoor seating make this a new favorite dive bar.”
No, because your friends don’t dance, and if they don’t dance, well, they’re no friends of mine.
I would love to be a hat guy but I don’t have the guts to try it out and stick with it. 
I would also love to be a cape, and possibly even an epaulettes guy if it were socially acceptable.
There is if you’re a Harold Lloyd fan.
I have one!
In the last few years I’ve taken to wearing a fedora in cooler weather, and a Panama hat in hotter weather.
Dang, I was all expecting to be like “stupid hipster kids and their damn hats”
But your son wears that hat well. Sharp-looking young man. Tell him to keep it up.
Are you sure that’s a fedora? It looks more like a porkpie to me. At any rate, he wears it well, and looks good in it.
I like to wear my hats from time to time. Among my favourites are an Australian bush hat that I like to wear when I’m out for a walk (no, it does not have corks dangling from it; it looks more like this); and a cowboy hat that I wear occasionally. (See my SDMB photo in the portrait gallery.)
I’d like to find a nice fedora. I’ve worn them when I’ve played in community theatre, and they look good.
Or, like asking your choice of if you’d rather piss your pants, or crap your pants.
ETA: James Tiberius Kirk, by the way.
Getting back to the thread, when I ride my motorcycle, I wear my helmet. That counts as a hat, right?
Well if we’re going to count helmets, I also have 2 Roman legionair ones, a Samurai helmet and a British Boer War pith.
A porkpie is circular, so I wouldn’t call the hat in the picture a porkpie. But its brim is rather narrow, so I would hesitate to call it a fedora. I would call that hat a trilby.
I wear anAussie Hat while walking the dog. Good for keeping the sun out of my eyes or the rain off my head. Bought years ago in the French Market in New Orleans on my first holiday to somewhere that far south and discovered how strong the sun was!
ps No corks and I don’t clip up one side!
Also, when it’s cold out I’ll wear a knit watch cap. Our Canadian friends might call that a Canadian toque?
Or, my Kangol Rain Tweed Trapper.
I don’t see why we would. A toque is any knitted winter hat. And it’s just “toque”–I’ve never heard anyone say “Canadian toque.”