Playing

Episode 1: Ty Burrell Wears a Chambray Shirt and Clear Frame Glasses

Episode 2: Maya Rudolph Wears a Black Skirt and Strappy Sandals

Episode 3: Schoolboy Q Wears a Patterned Bucket Hat and Glasses

Episode 4: Eddie George Wears a Navy Suit and Half-Zip Pullover

Episode 5: Simon Helberg wears a Sky Blue Button Down and Jeans

Episode 6: Mark Duplass Wears a Striped Sweater and Jeans

Episode 7: Kid Cudi Wears a Denim Shirt and Red Sneakers

Episode 8: Jesse Tyler Ferguson Wears a Brown Checked Shirt and Stripey Socks

Episode 9: Dax Shepard Wears a Heather Grey Shirt and Black Blazer

Episode 10: Zach Galifianakis Wears Grey Corduroys and Brown Leather Shoes

Episode 11: Joseph Gordon-Levitt Wears a Heart T-Shirt and Blue Jeans

Episode 12: Jack Black Wears an Embroidered Cowboy Shirt and Ox Blood Sneakers

Episode 13: Joel McHale Wears a Navy Zip-up and High Tops

Episode 14: Lil Jon Wears a Baseball Cap and Sunglasses

Episode 15: Colin Hanks Wears a Denim Button Down and Black Sneakers

Episode 16: Skylar Astin Wears Blue Jeans and Weathered Brown Desert Boots

Episode 17: Michael Sheen Wears a Plaid Button Down and Grey Blazer

Episode 18: Thomas Middleditch Wears an Enigmatic Sweatshirt and Sweatpants with Pockets

Episode 19: Karen Gillan Wears a Black and White Striped Pullover and Coral Skirt

Episode 20: Judd Apatow Wears a Polo and Blue Suede Shoes

Episode 21: Michael Cera Wears a Yellow Collared Shirt and White Sneakers

Episode 22: James Marsden Wears Gray Pants and Black High-Top Sneakers

Episode 23: Brie Larson Wears a Billowy Long-Sleeve Shirt and White Saddle Shoes

Episode 24: Carly Rae Jepsen Wears a Chunky Necklace and Black Ankle Boots

Episode 25: Mary Elizabeth Winstead Wears an A-Line Skirt and Pointy Black Boots

Episode 26: Tom Lennon Wears Black Slacks and a Black Skinny Tie

Episode 27: Ken Marino Wears a Slim Gray Suit and Salmon Tie

Episode 28: Randall Park Wears Brown Dress Shoes With Blue Socks

Episode 29: A$AP Rocky Wears a Black Button Up Jacket and Black Sneakers

Episode 30: "Weird Al" Yankovic Wears a Different Hawaiian Shirt

Episode 31: Uzo Aduba Wears A White Blouse And Royal Blue Heels

Episode 32: Judy Greer Wears a Navy Blouse and Strappy Sandals

Episode 33: Stephen Merchant Wears a Checkered Shirt and Rolled Up Jeans

Episode 34: Robert Kirkman Wears a Tan Blazer and Red Suit Pants

Episode 35: David Krumholtz Wears a Blue Zip-Up Jacket and Grey Sneakers

Episode 36: Michelle Monaghan Wears a Burnt Orange Dress and White Heels

Episode 37: Jake Johnson Wears a Light Blue Button-Up Shirt and Brown Shoes

Episode 38: Adam Pally Wears a Navy Blazer and Bright Blue Sneakers

Episode 39: Kathryn Hahn Wears Ripped Jeans and Black Heels

Episode 40: Josh Groban Wears a Blue Blazer and Shiny Black Shoes