Through the Looking Glass, Column 13

Face and Hair Revisited Part 3

As I explained last month, there is a widely accepted theory behind the practice of hairdressing. It can help make sense of a world of confusing possibilities and guide you to the ones that might be right for you. Remember faces are like pictures, and hairstyles picture frames. Or faces are like bodies, and hairstyles are like clothes. Last month we started out with that ideal form, the perfectly oval female face. Today I’ll talk about the other common female forms, the diamond, heart, and circle, and the three common male forms, the square, rectangle, and triangle, and how to choose the most transformative wigs and hairstyles. By and large, men’s faces are too long and wide at jaw to be mistaken for women’s faces—even if your beard has been lasered off and you’ve never really had a “brow bone,” like me.

Let’s start with the most male of shapes, the triangle or pear or, as some would say, the lantern-shaped face. (Please see the attached diagram so that you know exactly what I’m talking about.) The key to “correcting” this kind of face is to style hair so as to puff out the relatively narrow parts of your face and make the outer edge of your hairstyle be more of an oval even if your real face is not. Basically you need styles that are full at the temples and taper at the jaw. Or you can use the trick I stumbled into the first time I ever donned a wig. Tuck your hair behind one or both ears, and it will naturally puff out in just the right places. Shorter haircuts can also help balance your jaw, and wedges and shags can look amazing on you. If you go with long hair, you’ll want to keep it tight at the nape of your neck so that it doesn’t add fullness to your lower face.

Now let’s consider the square shape. It’s essentially like the triangle except that it’s not quite so wide at the jaw angles and may feature an equally squarish hairline. Among the more common male faces, this one is shared by many women and transforms rather well. Here again, though, you’ll want to go with shorter styles or long ones that don’t add fullness to the jaw. Layers and waves are great for they can break up the linear edges of your face and create a nice roundness to the outer edge of your hair-do. Wispy bangs and off-center parts will work wonders for your hairline, and height at the crown will help ovalize your over-all appearance! Whatever you do, don’t wear a straight bob ending at the jaw line. Instead, try a layered one that ends just above or below.

Ah yes, and now we get to the rectangular face. I believe that most men have a face that is just too long for womanhood, or like me, have a face that’s both too long and a little too wide. In designing a new style for me, Young Lee kept both these factors in mind. And, in the attached picture, see for yourself what she came up with. Of course, women too have rectangular faces, though theirs are usually caused more by narrowness than length. Long-faced lasses should avoid long hair. Keep it above your shoulders, ladies, because it can really make your face look even longer. Your crown should be kept relatively flat, and, just like with a square face, round out the sides of your silhouette with wavy hair cut in layers. Off-center and side parts break-up lines, and wispy bangs are essential in shortening your face.

Although round faces are more typically female, some of us males can look circular too, especially as we put on weight. In many ways the circle is like the anti-rectangle. Round-face ladies should try adding fullness at the crown and hair longer than chin-length. Sweep your hair back tightly on the sides of your face with clips or a ponytail. Like with all faces so far, an off-center part is recommended. Don’t wear bangs, and remember no rounded bobs to the chin, unless you want to look like Mrs. Pumpkinhead.

As we move from the oval face into the heart and diamond faces, we go from the ideal to the perhaps-even-a-little-too-womanly. A heart-shaped face is wide at the forehead and cheekbones and narrows down to a delicate chin. It can just as easily be thought of as an upside-down triangle. Off-center parts are favored on such a face as they are on nearly all non-ovals. Use wispy bangs and sweep layers forward to disguise the width of your forehead. A chin-length bob can be magnificent for you because it fills out your silhouette precisely where you need it the most. Longer hair is better than short. But if you must go short, be sure to leave sufficient fullness at the nape of your neck. Don’t add too much fluff around the top of your head because the last thing you want to do is look top heavy.

A diamond-shaped face is widest at the cheekbones and narrow across the forehead and jaw line. In many ways, a diamond face is a cross between a heart and a rather dramatic oval. Like with an oval, you can wear a tremendous variety of styles, especially around your upper face. Don’t hide behind your hair. Skip the bangs, try a center part, and cut your hair all one length if you like. But remember to handle your delicate chin with care. Just like with a heart-shaped face, medium-to-long hair works best with most of its volume at or below your chin and at the nape of your neck.

Well, that concludes my discussion of hairstyling for the seven major face shapes. You may check out to learn more. Be flexible and practical in how you apply these principles, but always consider what your hair does for your face if you’re to truly have a hair-do rather than a hair-don’t.

Life’s rich, complex, and full of possibilities. Be careful and enjoy!

Alice Novic, M.D.

To learn more about me than you’d ever dare to ask, please see my smart, sexy memoir, Alice in Genderland: A Crossdresser Comes of Age.

Also, if you wish to eMail Alice with Questions, Comments or Topics for Future Through the Looking Glass Articles, feel free to send her an eMail at or to Post any Comments below.