Photo: Gregor Halenda

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Lifetime Achievement Award
The boyfriend watch has evolved from trend to classic. The chunky design is, well, timeless, and it's available in a multitude of finishes and metals. Like the boyfriend jean, jacket, and shirt, the more casually you wear it, the better.

From top to bottom: Tag Heuer, $1,900, 610-491-8801. Movado Bold, $850, . Victorinox Swiss Army, $775, Marc by Marc Jacobs, $300, 877-707-6272. Fossil $145,