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Episodes
| # | Title | Watch |
|---|---|---|
| 1 | Patton Oswalt Wears a Black Blazer and Dress Shoes | Playing |
| 2 | Craig Robinson Wears a Bordeaux Button Down & Dark Jeans | Play |
| 3 | Jenna Fischer Wears a Floral Blouse & Black Heels | Play |
| 4 | Fred Armisen Wears Black Jeans & Glasses | Play |
| 5 | Zach Galifianakis Wears a One-Armed Jacket | Play |
| 6 | Nick Offerman Wears a Green Flannel Shirt & Brown Boots | Play |
| 7 | Lizzy Caplan Wears All Black & Powder Blue Espadrilles | Play |
| 8 | Tony Hawk Wears a Plaid Shirt & a Silver Watch | Play |
| 9 | Alison Brie Wears a Black Mesh Top & Mini-Skirt | Play |
| 10 | Josh Groban Wears a Suit & Striped Socks | Play |
| 11 | Ellie Kemper Wears a Purple Ruffled Sleeveless Top & Lavender Flats | Play |
| 12 | Steven Yeun Wears Rolled Up Black Jeans & No Socks | Play |
| 13 | Wayne Coyne Wears a Halloween Costume | Play |
| 14 | Dane Cook Wears a Black Blazer & Tailored Pants | Play |
| 15 | Chris Hardwick Wears a Black Polo & Weathered Boots | Play |
| 16 | Amber Tamblyn Wears a Leather Jacket & Black Booties | Play |
| 17 | Kevin Smith Wears a Hockey Jersey & Jean Shorts | Play |
| 18 | Rob Corddry Wears Tan Dress Shoes & Red Socks | Play |
| 19 | Eric Andre Wears a Cat Collage Shirt & Sneakers | Play |
| 20 | The Lonely Island Wear Holiday Sweaters & White Pants | Play |
