speaking as a glider pilot id love to get some shirts like these:
http://store.ssa.org/cgi/display.cgi?item_num=350 and some white pants, cargo like with a bunch of pockets, semi-lightweight fabric.
a good floppy hat with a smallish brim around the front but long in the back to cover the neck would be nice. helps prevent the sunburn but still allows good visibility.
if he wears glasses and doesnt have any set him up with some prescription sunglasses. do some research on the web or maybe the rec.aviation.soaring newsgroup (groups.google.com/group/rec.aviation.soaring) for info on the best tint. I've seen lots of guys with sort of a red/pink tint.
A SPOT tracker if you don't like to drive the chase vehicle and wonder where he is while he is flying around on the weekends. If he doesnt already have one of course.
Winter is comming up. Winning II by George Moffatt is a good book. Also I've been enjoying reading Once Upon a Thermal by Dick Wolters. Not sure if it is still in print. Lots of good soaring books out there.
If you are looking for places to shop, Paul Remde runs Cumulus Soaring and has a wide selection of glider geek stuff.
www.cumulus-soaring.com Also Tom Knauff has an equally large supply of stuff.
www.eglider.org I think.
You could always just spend a few weekends at the airport with him, helping out, if you don't already of course. I know that I really like having my favorite person at the airport to help me assemble and get launched is about the best gift I could ask for. Its also awesome to hear her voice on the radio when she's driving the chase vehicle. For a glider pilot having your significant other to send you off and be there when you land is pretty much nirvana.