Julia Citrin

If you have been keeping up with your beauty magazines, you’ll have noticed an increase in the number of famous actresses and singers who have cut their hair short. Short short. Not short like a bob hairdo, short like my father Bob’s hairdo. Perhaps you would like to cut your hair short, but you’re afraid it will look bad, or that people will make assumptions about you. These are rational fears—make no mistake about it—but if you follow certain guidelines, you can make the successful transition to life as a short-haired female.

First, find some photographs of women with short hairstyles you like—you’ll want to bring a few to show your hairdresser. Useful Internet search engine keywords include very short, super short, pixie, boy, boyish, androgynous, masculine, lesbian, queer cut, and alternative lifestyle haircut. While you hunt, keep an eye out for botched cuts—it never hurts to be prepared for the worst-case scenario. Have realistic expectations.

After doing a few months of research, take some time to reflect: is short hair really right for you? Useful during this period of reflection is a mirror. Look at one and ask yourself a few questions. Do you like tweezing and fashion? Kim Lepine of the Kim Lepine Salon says that short-haired women must “maintain a well-shaped brow,” and “dress with great style.” Are you already attractive? A woman who looks attractive with short hair, Lepine says, has “small features, a strong jaw line, and a well-proportioned face, ...