Good news, you tend to care less about stylish by the time you need bifocals. I have leveled up to the point at which I can wear bifocals and suspenders without giving any fucks. Probably because they no longer alter my probability of getting one.
Agree fully, as I put on the dorkiest headband in the world to capture sweat from my forehead as I work outside. It's not that we older folds don't care what people think, but more like we now realize that people rarely care or think about others who aren't close to them. Those few dozen people that see me in my dorky headband won't even remember my face in 15 seconds.