I love, love, love that bag! I don't think there is much from the Legacy line that will look outdated very quickly. The styles, the turnlocks, the pockets are all classic
Coach and ought to easily work for as many years as the bag lasts. I don't have the bag, but I think the only conern about it I've heard is that it can be a bit heavy, but a lot of that depends on the person and what you are used to carrying.