You know, I don't think I had any tall boots until a year or two later. (and then they had chunky heels). Let's see in '99, I was in college (sophomore and junior year) and I wore mostly sneakers, mary jane heels (for dressier stuff) and boots like these:
http://s7ondemand7.scene7.com/.....,2000,3200
except mine were deer skin and I had really pretty engraved silver kilties (the little scallopy thing at the base of the laces) instead of the leather ones).
DH and I started dating in '99, too, and for our first date I wore the mary janes. (although our first date happened a month or so after we started dating - we were in a band together and hung out all the time so the first date wasn't such a milestone!)
Oh, I do have a pic of the two of us right after we started dating - in a battle of the bands contest:
http://i31.photobucket.com/alb.....4a-011.jpg
(DH was really the bass player-I was mostly the lead singer-but we needed horns for this one song and DH played trumpet and trombone so he taught me the bass line for this one song).