I'm a child of the 90's so here's my fave GAP ads from that period. They helped define an epoch. Post your faves from that era.
Gap a go go
https://youtube.com/watch?v=z4kfS4rQi3M
Khakis ROCK
https://youtube.com/watch?v=ux0h4nU-Xig
Khaki Swing (I actually took swing lessons in the late 90's ala the movie "Swingers")
https://youtube.com/watch?v=knW1hGwmEXQ
Everyone in Leather -- this ad epitomized the time in the 90s when everyone and his grandma was sporting a leather jacket
https://youtube.com/watch?v=9m_X1Lm7dqo
Here's a more recent one featuring Clare Danes
https://youtube.com/watch?v=pmKacuH_xOU