I'm assuming "Mrs. T" wants something easy to use. iPod, hands down.
of course, I may be biased ... proud owner of one

... but magazine reviews for the past few years tout its ease of use. Even the latest issue of Mobile PC magazine questioned why the iPod was still the most popular music player even though more feature-ful and less costly players are now out there, and ease of use remained the primary reason.
There are tons of accessories out for it too, you have a choice of ten or 15 different cases (with belt hooks) for it: leather, 'skin' plastic, hard plastic, Neoprene, the list goes on!