Let's define exactly what it is to "Kick it Oldschool" as seen by the Webster's Dictionary.

Kick: a blow or thrust with the foot; esp. a propelling of a ball with the foot.
it: that one---used of a lifeless thing, a plant, a person or animal, or an abstract entity. used as an anticipatory subject or object (ex. It's good to see you)
Old: 1.having existed for a specified period of time. 2.of or relating to an era. 3. advanced in years 4. showing the effects of age or use
school: 1. an institution for teaching and learning. 2.a body of persons of like opinions or beliefs.

So clearly to "Kick it Oldschool" means to thrust with the foot at a lifeless thing, a plant, a person or animal, or an abstract entity that existed for a specified period of time and that pretains to another era within an institution for teaching and learning. See, you learn something new every day.

If thats not enough for you, oldster is a word. It sounds like something from the copy guy from SNL. The Oldster, Olderinie, Older-rama, making copies.

note: neither words "olderinie" or "older-rama" appear in the dictionary or in everyday conversations.