Capt Jack Sparrow would be fun 🏴☠️
Hmm. My first reaction would be "James Bond" but let's get real. No one is letting an older guy with a bit of a "Dad bod" into the tux. But there's another superspy who relied on brains and whose age and world-weariness was part of his character: George Smiley (from a number of John Le Carre novels and films/TV shows adapted from them). So that.
Also, Obi-wan Kenobi. I used to lean more to Luke, but nowadays Obi-Wan seems more my speed.
A woman goes shopping in the local mall. But what the heck is she shopping for in that outfit? My Festive Flash comp entry.