Top hairstylist John Frieda developed a measurement that helps determine if short hair is flattering for individual faces. From there, it's a matter of selecting a short hairstyle that flatters your face shape.
The angle of the jawline determines the measurement for whether short hair is flattering for your face shape. To measure the angle, place a pencil under your chin horizontally. Place a ruler under your ear, and angle it so it's perpendicular to the pencil. Note where the pencil lands on the ruler.
If the measurement is under 2.25 inches, then short hair is flattering for your face. If it is more than 2.25 inches, short hair is unlikely to be flattering.
If the measurement indicates short hair is flattering, choose a hairstyle according to face shape. Pixie haircuts look good on oval, round and heart-shaped faces. The hairstyle is especially flattering for round faces because it provides angles to soften the shape, according to About Style.
Angled bangs swept to the side are also flattering on round faces as well as long faces. Any hairstyle with volume on the sides looks good on long faces. Shags are flattering for heart-shaped faces.
For a square face, an A-line bob works well. This hairstyle is short in back and longer in front. The front should hit at or below the jawline.