Was there anyone more cool than James Dean in the 1950s? He made the pompadour haircut famous, and men have been wearing it ever since. To have the haircut behave the way it's intended, the sides of the hair are cut short and combed close to the head. The top is swept high over the forehead and held in place with pomade. The hair on the top can be teased up high or combed back in a flattering style to disguise the length.
Cutting the Pompadour
Comb the sides of the hair back horizontally behind the ear.
Make a part at the temple on either side of the head. Taper the sides of the hair from the part down. The length should be short so it can be combed close to the scalp, but long enough to blend in with the top.
Trim the back of the hair to match the length of the sides.
Comb the top, uncut portion of the hair down over the forehead. For a pompadour, the length should reach at least the eyebrows. If it's cut any shorter, it'll be too short to style correctly. Generally, this is at least 3 inches, but the top of the hair can be left even longer. The length will determine how much height the pompadour has on top.
Styling the Pompadour
Put two fingers in the jar of pomade and scoop out a large dab. Rub the pomade together in your palms and run it evenly through the top portion of your hair. You may need more, depending on the length of your hair.
Comb your hair back until it's slick and smooth.
Place one hand on the top of your head in the middle. Push the hair forward while combing the hair in the front straight up. You are trying to create a wedge shape from the front to the back.
Blend the sides into the top so there is no separation. Use more pomade if necessary.
Bring one strand down onto your forehead if your hair is curly and long enough.
Blow dry the pompadour in place if that helps cement the shape. Use your fingers to loosen the hair in front and bring it toward your forehead if you want a more relaxed look.
Modern pompadours are often worn by the rockabilly set. Women can also wear a pompadour hairstyle.