One tack is to buy a much-improved version of a piece of gear that he already has. For example, a bike pump. That's something he probably uses almost every time he rides, and perhaps bought four or five years ago. Go out in the garage and look for his pump. Right now. Yes, we'll wait.
Dum-da-dum. Deedle-do-doo. I'm dreaming of a umm-hmmm-mmm. Sleigh bells ring, are ya listenin'B
OK, you're back. Does it look sort of beat up? Good, problem solved. Go to your local bike shop or an online retailer and get him a Zefal Husky pump ($54). This is a well-made, super-efficient pump, with a wooden handle and steel body. My guess is he'd never spring that kind of money on a pump. But this would be the last pump he'd ever need.
A new helmet is something else that he probably could use. Depending on usage, helmets should be replaced every four or five yearsmore often if they're very sweaty or have been in the sun a lot. And helmets just get better every year. The Giro Havoc is a great mountain-bike helmetcool and light, with a visor and lots of vents. It retails at $100, but Nashbar.com currently has it for $55. Bell's X-Ray Pro is another good, mountain-bike-specific helmet for $100.
Of course, new jerseys are always appreciated. Cannondale's Team Jersey is a long-sleeve piece made with Polartec's excellent Powerdry fabric, available in Volvo or Saeco designs for $85. The same jersey in a single-color style is $55. I've been wearing these the past two months, and they're wonderful jerseys.
There, that oughta do it. Anything he doesn't like, send to me.