Dewey graduated from Davidson College in 1999 with a Bachelor of Science degree in Biology. In 2007, he earned his Master of Architecture degree from Rice University. He has practiced with architectural firms in Charleston, Florence and Columbia, South Carolina. He has been the project architect of medical, judicial, government and academic projects. He currently owns his own practice in Columbia. Dewey has served on the local chapter board of the American Institute of Architects as well as the South Carolina AIA Political Action Committee. He has served on committees of the National Council of Architectural Registration Boards, including the test writing committee for the Architect Registration Exam.
Dewey and his wife, Heathwood Alum, Ann Harriott Fisher Ervin, M.D., are the parents of Phillip '27 and Eloise '28. Dewey and Ann Harriott, both are members of the Davidson College Class of 1999, are active in the Columbia Area Davidson College Alumni Association. They are members of Trinity Episcopal Cathedral.