This article is about the a cappella group; for other meanings, see five o'clock shadow.

Five O'Clock Shadow is an a cappella group from Boston, Massachusetts, that has been in existence since 1991. The band has performed on FOX News, A&E Network, ABC, ESPN and VH-1's "breakthrough" series. They have released 4 cassettes and 6 CDs, winning many Contemporary A Cappella Recording Awards.

The group has toured with many famous acts including The Boston Pops, Aaron Neville, Edwin McCain, Patty LaBelle, Kool and the Gang, Blessed Union of Souls and James Brown.