Mary Elizabeth Winstead Wears an A-Line Skirt and Pointy Black Boots

1. Ty Burrell Wears a Chambray Shirt and Clear Frame Glasses2015-01-09 2. Maya Rudolph Wears a Black Skirt and Strappy Sandals2015-01-16 3. Schoolboy Q Wears a Patterned Bucket Hat and Glasses2015-01-23 4. Eddie George Wears a Navy Suit and Half-Zip Pullover2015-01-30 5. Simon Helberg wears a Sky Blue Button Down and Jeans2015-02-06 6. Mark Duplass Wears a Striped Sweater and Jeans2015-02-13 7. Kid Cudi Wears a Denim Shirt and Red Sneakers2015-02-20 8. Jesse Tyler Ferguson Wears a Brown Checked Shirt and Stripey Socks2015-02-27 9. Dax Shepard Wears a Heather Grey Shirt and Black Blazer2015-03-06 10. Zach Galifianakis Wears Grey Corduroys and Brown Leather Shoes2015-03-13 11. Joseph Gordon-Levitt Wears a Heart T-Shirt and Blue Jeans2015-04-03 12. Jack Black Wears an Embroidered Cowboy Shirt and Ox Blood Sneakers2015-04-10 13. Joel McHale Wears a Navy Zip-up and High Tops2015-04-17 14. Lil Jon Wears a Baseball Cap and Sunglasses2015-04-24 15. Colin Hanks Wears a Denim Button Down and Black Sneakers2015-05-01 16. Skylar Astin Wears Blue Jeans and Weathered Brown Desert Boots2015-05-08 17. Michael Sheen Wears a Plaid Button Down and Grey Blazer2015-05-15 18. Thomas Middleditch Wears an Enigmatic Sweatshirt and Sweatpants with Pockets2015-05-22 19. Karen Gillan Wears a Black and White Striped Pullover and Coral Skirt2015-05-28 20. Judd Apatow Wears a Polo and Blue Suede Shoes2015-06-04 21. Michael Cera Wears a Yellow Collared Shirt and White Sneakers2015-07-09 22. James Marsden Wears Gray Pants and Black High-Top Sneakers2015-07-16 23. Brie Larson Wears a Billowy Long-Sleeve Shirt and White Saddle Shoes2015-07-23 24. Carly Rae Jepsen Wears a Chunky Necklace and Black Ankle Boots2015-07-30 25. Mary Elizabeth Winstead Wears an A-Line Skirt and Pointy Black Boots2015-08-06 26. Tom Lennon Wears Black Slacks and a Black Skinny Tie2015-08-13 27. Ken Marino Wears a Slim Gray Suit and Salmon Tie2015-08-20 28. Randall Park Wears Brown Dress Shoes With Blue Socks2015-08-27 29. A$AP Rocky Wears a Black Button Up Jacket and Black Sneakers2015-09-03 30. "Weird Al" Yankovic Wears a Different Hawaiian Shirt2015-09-10 31. Uzo Aduba Wears A White Blouse And Royal Blue Heels2015-10-08 32. Judy Greer Wears a Navy Blouse and Strappy Sandals2015-10-15 33. Stephen Merchant Wears a Checkered Shirt and Rolled Up Jeans2015-10-22 34. Robert Kirkman Wears a Tan Blazer and Red Suit Pants2015-10-29 35. David Krumholtz Wears a Blue Zip-Up Jacket and Grey Sneakers2015-11-05 36. Michelle Monaghan Wears a Burnt Orange Dress and White Heels2015-11-12 37. Jake Johnson Wears a Light Blue Button-Up Shirt and Brown Shoes2015-11-19 38. Adam Pally Wears a Navy Blazer and Bright Blue Sneakers2015-12-03 39. Kathryn Hahn Wears Ripped Jeans and Black Heels2015-12-03 40. Josh Groban Wears a Blue Blazer and Shiny Black Shoes2015-12-10