It's a fantasy role-playing game.

DM: You are Jester Lavorre, a tiefling cleric . You are the member of the famous group of adventurers. Previously,  You had discussed with them, last time, a plot - fixing their seemingly not-very-well-put-together plot into a better direction (thankfully) - to acquire a wax seal within the home of Lord Sutan, to create a letter that you feel would be incriminating. Then to infiltrate the High Richter's home, do the same, and then report them to the Lawmaster or whoever else you think would be of higher estate...
DM: You, however, you make your way to the Song and Supper, and on the inside, you can see, nervously at a table, in a dark cloak, Ulog. "What the--?" Gets up and meets you outside, shoves you back out there and you both begin to walk side-by-side. "I was waiting here long enough!"
Player: We were waiting for you! It’s so weird that we totally missed you, though.
DM: Make a deception check.
Player: Well, well, well, 11.
DM: He goes, "Right. Well, where’s the rest of your team?"
Player: They are-- Here’s the thing. How rich do you look? How rich does he look?
DM: He looks down and he has fairly plain dark clothing for night-stealthing. He has like a single-- looks like a gold chain of some kind with a single yellowish amber-orange bead on it that looks like it’s worth a gold or two. Dark green-brown cloak. It’s hard to see the color, this late at night. He doesn’t look super rich.
Player: Can I put some of my costume on him?
DM: Yeah.
Player: I’ll put some of my festive wear on him.
DM: You put some of the festive wear on him. It’s all not at all fitted for him and it looks like a kid who has outgrown his snow-outfit and he’s like-- "This is humiliating."
Player: It’ll get you in the door, don’t worry. Here, put this mask on.
DM: He’s seething beneath it. You can see him grinding his teeth, but he follows you nevertheless.
