Friend turned 40 and is trying to dress the part. What $300-500 gift would up his style most?

Hey MFA. I want to get my buddy something meaningful—a nice jacket, a good starter watch, some decent shades—but I can only spend up to $500 and want to avoid spoiling the surprise ahead of time. His style is pretty grounded. Earth tones, vaguely woodsy, but neither preppy nor overly utilitarian. What's a good addition to his wardrobe that I can safely cop without the benefit of him trying it on in advance? Thanks much!