>>2705055The left one is a Shady Brady, actually one of the last ones ever made by the original owner of the brand before he died in 2017 but I've been to the new owners' shop/factory and the new ones seem just as good. (Still made in a little shop in the USA using the same equipment and materials, just moved to a different building.)
The one on the right is an old Stetson, not sure the exact date but probably '80s or early '90s, found it new old stock and covered in dust in the corner of a local western store and the label inside was a form with old-school dot matrix printing so that kinda dates it. It's pretty fragile due to its age so it doesn't go /out/ anymore, only gets worn for special occasions.