"He's hard to buy for" usually just means the default gifts (socks, aftershave, a tie) have been tried and haven't landed. The better approach is starting from what he actually spends time on.
A proper tool upgrade, a kit for a hobby he's mentioned wanting to try, or something for whatever he's currently fixing/building tends to beat anything generic, because it plugs directly into something he already cares about.
A tasting experience, a well-chosen bottle from a style he doesn't usually buy for himself, or a proper piece of kitchen kit he's been putting off buying: these read as "I noticed what you're into," not just "happy birthday."
Good travel gear, noise-cancelling headphones, or a proper day bag get used on every trip afterward, which is exactly what makes a gift feel worth it in hindsight.
A lot of people are genuinely bad at spending money on themselves. A nicer version of something he already uses daily (a wallet, a watch strap, a decent razor) quietly fixes that on his behalf.
Tickets to something he'd never quite justify buying for himself (a match, a gig, a track day) tend to be remembered long after anything wrapped in paper.
Not sure which direction to go? Search for a few real options on Hey Yoink and share the list with him directly (or with whoever's helping you decide): he can react to actual products rather than you guessing blind.
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