Hipness Purgatory is a loose aesthetic movement spanning from 2004 to 2013, associated with the Hipster movement, peaking in popularity around the very late 2000s to early 2010s. Characterized by loose drawings, feeling handcrafted with everyday objects, an ironic tone, and a "twee" retro/ indie atmosphere. The style has been associated with "millennial optimism".

The aesthetic first emerged in the early 2000s and grew predominantly out of the hipster and twee/anti-folk movements. It was closely associated with millennial art and aesthetics and was intertwined with the overall look of campy 2000s coming-of-age films and general media like Juno, Diary of a Wimpy Kid and Sorry, Thanks and directors like Wes Anderson. It drew influence from the twee pop and DIY indie movements of the '80s, by infusing their return to childlike innocence and raw simplistic authenticity, with ironic millennial hipster subversions , also later incorporating elements of recession era party and drug culture. Artists from New York City's Anti-Folk movement like Jeffrey Lewis, Walter Mitty and His Makeshift Orchestra, Wingnut Dishwashers Union, Jordaan Mason and the Horse Museum and Paul Baribeau's cover art work acted as early examples of the aesthetic.

The music tied to the aesthetic was often twee or folk, such as songs by The Moldy Peaches featured in Juno , or works by Sufjan Stevens. However, as the aesthetic evolved in the early 2010s, it became more broadly associated with youth culture. As a result, pop artists like Maroon 5 and swag era rappers Ruben Slikk and Lofty 305 from the collective Metro Zu began to incorporate the style as well. Television shows and cartoons such as Johnny Test , Regular Show , BoJack Horseman , Rick and Morty , Adventure Time , Bob's Burgers , and Superjail! also began to take influence from the movement, along with video games like Life is Strange and LittleBigPlanet .

At times, hipness purgatory evoked the looser maximalist psychedelic rock art of the late '60s, as well as the Hippie influenced underground comix scene indebted to artists like Robert Crumb. The general hippie drug culture inspired art of the late '60s to early '70s can be interpreted as overarching influences on the aesthetic as it mirrored the same drug culture associated with the hipster movement, as can be seen in the cover art of Maroon 5's Overexposed (2012) . Another possible influence might be outsider/naive art movements like the Chicago Imagists , as well as the comic book inspired art of Daniel Johnston .

The visuals of Hipness Purgatory consist of loose drawings, doodling and common objects and materials that mimic the feeling of a handcrafted scrapbook or notebook, especially with the use of line work similar to pencils, crayons, chalks, colored pencils, and markers, as well as materials/objects like cardboard, paper (white or colored), paint, stickers, and paperclips.