well, classic styles (the less the detail) would last longer. But some extreme trendy would definitely look dated. For example, the motor boots (all the buckles) are so hot right now, I predict that in 10 years, they WILL look dated, if one is wearing them with activities other than outdoors "riding"-ish activities, they will look totally off pairing them with a dress and jacket like we do now.
I think from the 80s, those big square toes with super big chunky heels would look "dated" if wearing them now.