You'll get a lot of opinions about what's best. I'm a pragmatist and a big fan of Casio electronic watches. They should be in your price range. Electronic watches aren't sexy, but mine has a variety of bells and whistles that make it extremely handy for me:
- data memory: I can store a limited amount of data (lock combinations, passwords, account numbers, phone numbers, etc.). This has become increasingly useful because my workplace has become more and more security conscious. Also useful for travel - do your remember your frequent flyer account numbers or your hotel rewards account numbers?
- second time zone: if he will be attending school in a time zone different than home, this allows checking the time at home quickly. (I love this feature for travel.)
-multiple alarms (though the alarm doesn't screech loud enough to get a real sleepy-head out of bed). He could set alarms for different classes, for example.
-timer (great for grilling - I don't overcook dinner any more.)
-stopwatch
-easy to read face with date, time, and day of the week / press a button to light the face up at night
I own 3 or 4 watches, but the Casio is so practical that it's the one I almost always wear.
(You're in Wrightwood, which is close to me. I found my watch at the Rancho Cucamonga Sears store (on Foothill near the 15) a year or two ago - about $130 and supposedly on sale.)