I once went with my now common law and his parents to Arizona (we live in canada). They have a vacation house down there and go twice a year. His uncle, also has a vacation home down there in Scotsdale. (The rich part I didn't know)

While we are in Arizona, we get an invitation to go for pizza with his aunt and uncle (who i hadnt met yet). I'm used to 10-20°C so the 50°C of Arizona was killing me. For pizza, I thought short shorts, flip flops and a baggy graphic t-shirt would be a good outfit.

I should have taken cues from bfs mom and dad who wore nicer than their usual vacation clothes and my bf and his brother wore button up shirts (my bf always does so not weird for him)

We get to the restaurant and I knew I messed up. It was FANCY PIZZA. THE TYPE WHERE THEY HAVE THEIR MICHELLIN STARS ON THE WALL.

Uncle was in a suit and aunt was wearing a womens business suit.

I didn't realize we were meeting the rich family and I look homeless. We sit down and waiters in suits attend to us. His aunt slides an envelope across the table to my bf and says "sorry we were in Greece for your birthday, here's something to make up for it" $1000 check. (They have kids and grandkids, the nephews aren't replacement kids) meanwhile I've never seen that much money at one time (at the time)

Then uncle starts talking about his various businesses and investment accounts

I have since seen them many times in appropriate attire and they now I'm not a homeless person he found on the street but damn that was scary