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- 1Patton Oswalt Wears a Black Blazer and Dress ShoesMay 8, 2014
- 2Craig Robinson Wears a Bordeaux Button Down and Dark JeansMay 15, 2014
- 3Jenna Fischer Wears a Floral Blouse and Black HeelsMay 22, 2014
- 4Fred Armisen Wears Black Jeans and GlassesMay 29, 2014
- 5Zach Galilfianakis Wears a One-Armed JacketJune 5, 2014
- 6Nick Offerman Wears a Green Flannel Shirt and Brown BootsJune 12, 2014
- 7Lizzy Caplan Wears All Black and Powder Blue EspadrillesJune 19, 2014
- 8Tony Hawk Wears a Plaid Shirt and Silver WatchJune 26, 2014
- 9Alison Brie Wears a Black Mesh Top and Mini-SkirtJuly 3, 2014
- 10Josh Groban Wears a Suit and Striped SocksJuly 10, 2014
- 11Ellie Kemper Wears A Purple Ruffled Sleeveless Top & Lavender FlatsOctober 17, 2014
- 12Steven Yeun Wears Rolled Up Black Jeans & No SocksOctober 24, 2014
- 13Wayne Coyne Wears A Halloween CostumeOctober 31, 2014
- 14Dane Cook Wears a Black Blazer & Tailored PantsNovember 7, 2014
- 15Chris Hardwick Wears a Black Polo & Weathered BootsNovember 14, 2014
- 16Amber Tamblyn Wears a Leather Jacket & Black BootiesNovember 21, 2014
- 17Kevin Smith Wears a Hockey Jersey & Jean ShortsNovember 28, 2014
- 18Rob Corddry Wears Tan Dress Shoes & Red SocksDecember 5, 2014
- 19Eric Andre Wears A Cat Collage Shirt & SneakersDecember 12, 2014
- 20The Lonely Island Wear Holiday Sweaters & White PantsDecember 19, 2014