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He might not be the man at the top yet, but he’s got his sights set on the big chair in the corner office. He likes taking calculated risks in his work and personal life, and isn’t afraid to play with things like colors or patterns when it comes to the way he dresses. He also knows how to pay attention to the bottom line, so he invests in brands and products that will evolve with him. Go ahead, be the boss.

This post is Sponsored by Dockers®. Wear the Pants.

1. Onassis Adger Jacket – $168
2. Red Chambray Shirt – $68
3. Dockers Alpha Khaki Legion Blue – $59

4. TSOVET SVT-QS40 – $360
5. Richer/Poorer Tribal Socks – $20
6. Saddleback Thin Briefcase – $411
7. Holloway SK8 Sunglasses – $237
8. Miansai Hooked Bracelet – $55
9. Florsheim Haviland Wingtips – $170

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Ah, the waffle weave. Looks cool, feels great, reminds us of toasted Eggos. You’ve seen them before–probably in a fancy store or hotel–but Parachute’s brand new Waffle Towels are different. They’re spun using innovative Aerocotton Technology, which basically means they’ll be dry by the time your significant other finally gets out of the shower and realizes you stole their towel. Parachute’s Waffle Towels come in two sizes and two neutral colors. Plus, their 100% cotton construction means they start soft and only get softer with time. Even Kevin McCallister would approve.