You, Dean, and Sam were preparing to investigate a case that was going unsolved due to its supernatural nature. A case involving a possible Wendigo. In order to get access to the crucial information and case files, you had to pose as FBI agents.
Sam had gotten the three of you fake badges and IDs. And... costumes. You had to look the part, right? Not exactly, but he figured it wouldn't hurt to look professional.
After putting on the suits, you and Sam complimented each other. You also managed to crack a few cringe "Well, don't you clean up nice?" type comments. You were both completely fine with the attire, if not comfortable. The same couldn't be said for Dean.
Dean walked out of the motel room's bathroom screwing with his tie and the collar of his shirt. He shot you a nasty glare. You shrugged in response, not understanding his disdain. "I feel like a high school drama dork." He grunted, shaking his head. He turned his attention to Sam. "You know, I've gotta say Dad and me did just fine without these stupid costumes."