In that case, if you know his style a nice briefcase. If not have Dh take him out to an adult dinner somewhere nice and go shopping for a briefcase before hand.

He's headed to a NYC investment firm.

Depends a little what he's doing next. Grad school or working? If working, and will be living on his own for the first time, I might suggest nice apartment stuff - a set of cookware or dishes or something like that. Or a gift certificate for Sur la Table. Luggage is a good choice too- my DC is graduating this year and has requested luggage.

What are his post graduation plans?

Last year my niece graduated HS. I gave her a piece of luggage with items in it. I wanted to give her something I knew whould last and be used for the next 5+ years so that she had luggage when she needed it for an interview or travel.

^ reread the post. Above maybe better for HS graduate on their way to college

My son really appreciated a nice sleeping bag. I'm not thinking this is necessarily a good godparent gift, but I'll mention in case others are reading. An LL Bean sleeping bag - good looking. It's extra bedding to grab and go, heading out the door when they're staying over somewhere. Can unzip and use on the bed as a comforter. Practical, useful, DS has never used it for camping.

Monogramed towels. Maybe this. DS liked these (husband thought he wouldn't, be he really did) I was going to go with something formal and adult but ended up with PB (maybe even PB kids) bright colors, stripes, more beachy.
DS like them.

I'm a big cash-as-gift-give, but some situations call for a "boxed gift" and I think this is one of them. I'm thinking a briefcase or nice weekend bag.

Check

Unless there is a specific request, go with a Visa gift card. It's not personalized but those other things are rarely useful to the new graduate.

DH looking for ideas for something really special. $250 maybe, but could be more or less. We used to get luggage, brief cases, pens -- what are today's good gifts?