Q: Hi Bill, I've been thinking about cutting my hair shorter, but I have no idea if it would look good on me.

My hair used to be long, but I recently cut it to chin-length in order to donate it. Since then, it has gotten to almost shoulder-length (a little longer than this photo, which was taken a couple months ago). 

Now I'm considering cutting it a lot shorter—even pixie-length—but I am unsure of what style would suit me best.

My hair is naturally wavy and brown, a pretty normal texture and medium thickness. What should I do with it? I'm up for anything. Thanks! — Alicia

A: Wow, what a natural beauty you are, Alicia. You could do almost anything with your hair.

If you want to ease your way into short hair, you could start by taking your bob up a few inches, to the jawline.

Adding some long layers is key to encourage your wave and natural movement.

Notice the cool texture of the waves in these photos. To achieve this, you can mist your hair with a texturizing spray (such as OUAI Wave Spray) and scrunch it through. 

Then I recommend letting your hair air-dry instead of blow-drying it. Once dry, avoid brushing or combing your hair. Instead, use your fingertips to rake a tiny bit of pomade (such as OUAI Matte Pomade) through the top layers to define the waves.

Also pay attention to where the hair is parted with the above styles. A deep side part or flipping your hair over to the opposite side will give you the most edge.

When you're ready to go shorter, this cut would be super-cool. Crop the back and sides but leave the fringe long, so you can flip it back and forth.

The same styling advice applies here to show off your natural texture. You can also use a curling wand or flat iron to add more or less curl through the fringe.

Finally, there is the pixie cut. With your face shape, wavy texture and natural colour, this would obviously be a great look for you.

And here are a couple different styling options. You can wear the bangs down, across your forehead.

Or shape them up and over to one side to elongate your face.

You didn't ask about your colour, but when you have short hair, it is the best time to play with different shades if you want drama. A dark rinse would be the easiest way to add more edge and make your eyes pop. 

Have fun with these suggestions, Alicia. 

billyxoxo