Ken Downing, senior vice president and fashion director at Neiman Marcus

“No one loves a hoodie more than Mark Zuckerberg–or me! They are a wardrobe staple for any cool guy. The hoodie is Zuckerberg’s signature. Stick with it and take it to the next level. I love the look of a hoodie under a jacket. He would look super cool in Prada, perfect for his lean frame. Brunello Cucinelli is the sweatshirt I would suggest. Casual yet lux. And while he is in the Brunello Cuccinelli territory, fine gauge knits look polished and still have a casual air. Lean and trim trousers or jeans always look great paired back to a hoodie and jacket. Dolce and Gabbana, Prada, DSquared all fit the bill and his body type. Trade in the dorm shower flip flops for a Gucci Chelsea boot. Comfort and cool with an edge.”