Each student has an advisor who carefully oversees her academic and social development. A student should feel free to seek out her advisor whenever she is in need of advice. Advisors are assigned to new students and some students stay with that faculty member during their time at Oldfields. Students may also request to change advisors if they feel they have bonded more closely with another faculty member. Advisors often have their advisees over for dinner or go off campus for special outings. In addition, the advisor is available to give his/her advisees their grades and comments at the end of each marking period. Advisors should be the first point of contact for parents when they have a question or comment regarding academic, athletic, or community life at Oldfields.

Each day begins with the advisory period when advisee groups meet together. During this time, there are announcements and time for group interaction. Students have the opportunity to feel connected to their peers and advisor.