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The Office is gearing up to end its epic nine season run on NBC. In its wake, the comedy has left us plenty of pranks, some great one-liners and most importantly, a set of characters so loveable and familiar it feels like we know them in real life. From their quirks to their fears, hopes, dreams, loves and longings, viewers have a great sense of what makes them tick and more superficially, have a great sense of how they put themselves together.
For almost a decade, we’ve watched these characters outfit themselves in some of the wildest, wackiest and most unintentionally stupid costumes one can imagine. They’ve made poor hairdying choices. They’ve repeatedly turned to the same pair of jeans, and they’ve busted out some costumes that clearly belong in another century. We could sit here and argue all day about what the funniest, most inappropriate or most telling fashion choices in the history of The Office are, but for me, when I look back, these are the fashion moments, styling trends or cosmetic quirks that stick out more than all of the rest.
Michael Scott instituted casual Fridays in The Office so that he can wear his fun jeans. One of the longest running gags and props on the show, the fun jeans are a particularly ordinary pair of blue jeans that seem to have magical powers on Michael’s personality. When the fun jeans are on the eclectic manager’s person, it gives the manager the license to be zanier and wilder than usual, running around the Scranton branch like a madman.
While Michael’s fun jeans are most often a regular pair of Levi’s, he has shown no loyalty to the color. In the episode, “The Convention,” Ryan looks over Michael’s checklist for the big trip, noticing it included three boxes of condoms and a pair of “white fun jeans.” These special fun jeans are hung on a hanger and wrapped in plastic for protection.
2. Angela’s Preoccupation With Wearing Kids Clothing
Angela is often noted for being a tiny member of The Office crew, and somewhat because of this, she’s had a slew of weird costumes over the years. My favorite outfit she ever wore came during Phyllis’ wedding, when Angela favored a powder blue suit from the sixties that looked like it belonged to a child. We already knew at that point that the woman loves children’s clothing, as evidenced in the episode “Women’s Appreciation Day.”
During the episode, Michael Scott is having trouble determining whether or not Jan is his soulmate and ends up taking the women to the shopping mall, where we find out Angela’s feelings about buying clothing from Gap Kids, as well as the American Girl store. You can catch that lovely sound bite in the above video, at around the 2:15 mark.
3. Creed’s Attempt To Look Young
Creed is normally a weirdo older dude who hangs out in the back of the office and tries to avoid getting noticed, as he rarely does any actual work. However, once in a blue moon, the full-on oddball in Creed comes out and comes out in epic proportion. One of the highlights of these moments is the time Creed decides he needs to pass himself off as far younger.
Between the rolled up sleeves, the loosened tie and the horrible dye job, as well as Creed’s vocalizations in the clip, this costume is the whole package and one of the skeeziest/funniest moments The Office has ever put together.
Dwight normally looks pretty basic when he heads to the Scranton office for work each morning, but we all know his true beet farm roots and, occasionally, we get to see zany costumes related to the other portion of his life. This was probably best shown during one of The Office’s Christmas episodes, when Dwight was determined to share his holiday traditions with his coworkers, traditions that are pretty opposite the American holiday traditons and also pretty racist.
If you haven’t caught the clip, I won’t spoil the whole Southern Germany Belsnickel look for you, suffice to say it features a disgusting beard, a whip, and plenty of disgusting brown fur. Also, Dwight loves it, and he always has a little Gollum in him when he gets overly excited about a particular tradition or activity.
5. Michael’s MISSterious Suit
Of course, Michael Scott makes this list more than once. Another Office plotline featuring plenty of amusement is the time when the women in the office get a glimpse of a pink label on one of Michael’s suits, soon noticing the feminine cut and shoulder pads in the look. A lady’s suit actually doesn’t look half bad on Michael, but the chuckle-inducing moment is one worth watching.
Honorable Mentions : True Blood Halloween costumes, Andy's Bracelet, Dwight's Overall Appearance, Ryan's my shit don't stink suits, David Wallace's sad, ratty sweatpants.
Please, let us know if there are any of great looks we missed in the comments, below and don't forget to check out The Office's finale on NBC May 16!