I received the classic, Hartmann belting leather hard case as a college graduation present (1990). I still have it; it's, as promised at the time, beautifully patina-d now. I think I last actually used it around... 1991? 1992? I should probably retrieve it from storage to see if there's anything inside it, like a time capsule.
The problem was that I went to grad school, and it simply wasn't a very useful bag format. You hame to lay it flat to open the top, and 90% of the time in grad school I was retrieving things on the go, or I was in a classroom with too-small desk tops, that kind of thing. *Now* I have a big desk, but it's at my *house*, so I'm not really using attaches!
I do think it's worth having a leather bag, even though they're heavy. Things that last are good.
If I were 25, I'd want the following in a bag:
- it protects my computer and other electronics
- I can retrieve items on-the-go, without needing to lay it down (like if I'm in a place, on a train, or my bag is on the floor next to my chair in a cafe)
- I can carry it cycling (ie. messenger bag style)
One saving grace of the modern world over the 90s/00s is that notebook computers are not small enough that you don't need "a computer bag" any more. My 2019 MacBook Pro slips easily into a thin case which itself slips easily into a "normal" attache. I'm partial to Swain Adeney's "Westminster Legal Case" in the American size ("London Tan" if you want patina in twenty years), but there are many functional equivalents.
(Caveat: if your boy is a hipster, he might very well appreciate an "ironic" case such as an old-school hard attache or document case. Caveat 2: if he's an attorney, well... they still make the hard, rolling document cases!)
My advice: an attache is as personal as a tie - it's just very difficult to buy one for someone without their input. I suggest a father/son outing, grab some coffee or lunch in town, visit the leather goods shop, buy him a briefcase of his choice. How often does that happen nowadays! It's a memory.
DH