Intramural softball (your team came in last)
Any fraternity-related event (maybe some charity you once supported?)
You were too cool to join any clubs.
A full seersucker suit
Nantucket reds, an old faded polo shirt, and a pair of Sperrys
Madras pants with a white button-down
Pastel pink shorts with a kelly green polo shirt and a popped collar
Just a tshirt and jeans
Gin and Tonic.
A cold beer, no frills.
An adopted mutt
A small yappy dog, perhaps a maltese?
A cocker spaniel
Drinks at the club, followed by a charity event at the same locale.
Cooking out with the guys, relaxing with a few beers, and playing some poker.
Throwback to the college days - playing a round of beerbong before heading to your girlfriends dinner party. Maybe accidentally blacking out in the process.
Having a few friends over for a movie.
Dinner at the newest restaurant in town, followed by making an appearance at a posh club.