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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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Tired of stuffing your pockets with gear? Don’t want to carry a bulky backpack everyday? With a NutSac bag, you can keep your all everyday carry essentials within arm’s reach without the extra bulk. Made in the USA with high-quality materials like waxed canvas and full grain leather, every one of the “NutSacs” in the collection is built to be beaten up and guaranteed for life. With different sizes based on your individual carrying needs, there’s at least one simple, comfortable and rugged bag that fits like a glove.