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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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A pocket square is a touch of old school class. It’s an element that casually lets people know you’re a gentleman. This knife from Gerber borrows its name from the humble pocket square because it too is sharp and dressy. Eschewing superfluous design elements for a sleek, clean appearance, the Gerber Pocket Square Knife is refined and mature. The machined aluminum handle is paired with a 3” drop point blade and an ambidextrous thumb lift for one stunning folder. If James Bond relied on a pocket knife, this would be it.