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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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Unzip your coat and have some mulled wine on the house—you’ve arrived at your final gifting destination: The Holiday Gift Guide. It’s like your friendly neighborhood one-stop holiday shop, except instead of balsa wood ornaments, ours is packed with thoughtful gifts for everyone on your list. Future heirlooms, small-but-significant stocking stuffers, and gear for getting out there (or staying in)—are all right here. There’s no music playing in the background though, so you’ll just have to hum Bing Crosby while you click around instead.

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