My Biggest Makeup Challenge

                                               The finished product (or part of it)

One of my first clients was someone I never pictured: A very masculine-looking man in his late 20s. He found my page on the Internet and reached out initially with an e-mail account using a female pseudonym.

Once I realized he was a man, my main concern had nothing to do with gender identity: It was with my own abilities. In all my years of practice with makeup, I'd never considered the techniques of how do makeup on a man.

There were added challenges: He didn't want to appear drag in any way. If you scan video tutorials, many male makeup looks are drag queen or essentially a look that's a parody of a woman. Nor did he want the Jared Leto guyliner look.

Ava (certain identifying details are changed) is someone who truly thinks he was born in the wrong body. He identifies with being female much more strongly than being male, but he's facing certain realities: Transgender surgery is extremely expensive, time-consuming, and painful. He's also approaching the age where his masculinity is becoming more pronounced: facial and body hair are becoming harder to tame; if he gains weight or muscle, it goes in all the traditionally "male places," such as the torso and shoulders. In other words, his testosterone is growing along with his desire to be a woman.

When I finally met Ava, I was overwhelmed at the task before me: His features and bone structure are a series of sharp angles and undeniably male. There was no unisex quality to his face or body. As a former high school athlete who continues to train, he's a handsome all-American jock. Even though he'd shaved a couple times that day, a strong outline of facial hair was apparent, as if taunting my plans.

As we spoke, I scanned his face, trying to figure out how to feminize each feature - the bushy brows, the pronounced jawline.. The other trick was Ava couldn't be altered in any way that would affect his everyday appearance, so I couldn't wax or pluck anything.

What I thought about the most in preparation and as I did his makeup was what makes a face feminine. Ironically, doing a man's makeup made me appreciate female beauty even more.

Here are the main components of a traditionally feminine face:

1. Our eyes and lips naturally have a stronger color contrast against the rest of our face than a man's do: This is perhaps why the smokey eye is so enduring in its popularity, as it plays on that contrast. This also explains our love for lipstick.

2. Our cheekbones are higher and more pronounced, which also explains our fascination with contouring and highlighting.

3. Our lips our generally fuller, which is due in part to estrogen levels: This is why full lips are often associated with youthful femininity. As we age, our lips naturally lose their fullness.

The longest part was covering his facial stubble: I've learned that taking an orange lipstick and brushing it along any dark areas will color correct this darkness. I actually broke a sweat while doing his makeup. Was I personally happy with my work? I wish I'd brought a kit to cover his brows and draw in more arched, slender ones. I wish I'd gone for broke on the eye makeup. His masculinity allowed for the excess I normally shy away from.

Most important was that Ava seemed happy with the final product. Despite the misnomers, I was reminded that makeup can sometimes bring out the truth and make us feel like more of ourselves.