|In the study group's first year at Greendale, Jeff strips down to his underwear while playing a game of pool against his billiards teacher Coach Bogner. The underwear is a striped polyester/cotton blend that has become a signature piece of clothing worn by Jeff. According to Britta he only wears the striped "Beetlejuice " numbers on special occasions. Its first appearance was in the Season One episode "Physical Education". The style of under garment makes several appearances throughout the rest of the series. They make no appearances in Season Five or Season Six.|
In his freshmen year at Greendale, Jeff is kicked out of his billiards class by the teacher Coach Bogner for refusing to wear the gym shorts required for the class. Jeff later becomes more comfortable wearing the uniform and confronts the Coach in the student lounge. A challenge is issued and they play a game of pool which quickly gets out of hand. In an effort to prove how he doesn't care how ridiculous he looks, Jeff strips down to his underwear revealing orange and black tiger striped boxers. Coach Bogner follows suit but then ups the ante by ripping his underwear off and playing his last shot naked. Jeff anticipated his response and ripped his underwear off as well throwing the under garment into the crowd which had gathered to witness the spectacle ("Physical Education").
The underwear is next seen in the study group's second year at school worn by Jeff while he is doing hanging sit-ups in his apartment ("Anthropology 101"). Later it makes an appearance when the study group searches for Annie's pen in Group Study Room F. In order to ensure no one has the pen on their person, the study group strips down to their underwear and Jeff is shown to be wearing a turquoise variation. Troy compliments his under garment noting how comfortable it seems while Britta teases him about using that particular clothing only on special occasions ("Cooperative Calligraphy"). At the end of the school year the underwear is seen again in a flashback when it's revealed that Jeff and Britta had been hooking up all year. Abed remembers seeing him and Britta in his dorm room wearing only their under garments with Jeff wearing a red and grey striped variation. Jeff's underwear is also seen when he recalls the cheap hotel with bedbugs they stay in ("Paradigms of Human Memory").
In the study group's third year at Greendale, Dean Pelton has a psychotic break after filming of a TV commercial for the school goes badly. He strips naked at one point and is shown to be wearing the exact same type of tiger striped underwear that Jeff wore when he played pool against Coach Bogner ("Documentary Filmmaking: Redux").
In the study group's fourth year at Greendale, Dean Pelton was pantsed by the Abed's Delta Cube fraternity. He was again shown to be wearing underwear similar to Jeff's ("Economics of Marine Biology"). The day before Jeff's graduation ceremony he has a daydream involving his Evil counterpart from the "Darkest Timeline". In it, Evil Jeff crossed over into the "Prime Timeline" wearing just his underwear ("Advanced Introduction to Finality").