This short Ivy League haircut is parted and brushed back on a slight angle. This cut, made popular at East Coast prep schools in the early 1900s retains its popularity today. You’ve seen this variations of this preppy haircut on Anderson Cooper, Justin Timberlake, and Matt Damon. Around the sides and back of the head, hair is tapered towards the nape of the neck and can be cut medium, short, or somewhere in between. More a modern twist, try the undercut.