For at least three adolescent years, I smiled like a serial killer: chin to my chest, eyes too wide, lips pressed into a manic smirk. It was not a pretty picture.

I was young and awkward, but I grew up—and grew confident and not so homicidal. I discovered newer and gentler poses for photographs. I dappled in duck faces and toothy grins. I blew ironic kisses to iPhone lenses. I even settled on the perfect angle for selfies. (Kylie Jenner is a prophet.) But the hundreds of tagged Facebook photos from this time are proof: I had forgotten how to smile.

I never take "real" pictures, which explains why I panicked when I was asked to supply a headshot for ELLE.com. The last time I sat for formal photos was Picture Day. I was 10. According to LinkedIn career expert Catherine Fisher, I'm in good company.

"There are a lot of bad photos [on LinkedIn]," Fisher concedes. "Unless you're a veterinarian, your dog should not be in this picture. Your significant other should not be in this picture. Unless you're a swimsuit model, you should not be on the beach in a bikini."

As a regular human, she tells me that I am supposed to look into the camera and pose without props: No spandex. No neon. No extra limbs.

"The 'third-arm photos!'" Fisher cries. "It is just so obvious when someone has cut a friend or a boyfriend or a significant other out of a photo. There is always an extra arm, slung over a shoulder or resting on a table or something. This photo is a first impression. You should be the only person in it."

After wasting too many minutes trying to transform an overexposed photo of "just me, no distractions" in a dark restaurant in Mexico into a decent portrait, I resolve to make time to take a nice picture. To ease the indignities of self-timers and Photo Booth, I mobilize a team of experts—a hairstylist, a makeup artist, a friend/photo editor. Of each, I make the same demand: "Smoke and mirrors, please."

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Hellin Kay
The Before...

The Hair

Veteran Bumble and bumble guru Joey Gallagher assures me I do not need pyrotechnics, but she does argue for exaggeration.

"A product like Thickening Hairspray is essential," she says. "It adds volume and makes the blowout last."

I think of pageant queens and Real Housewives and protest. I tell Gallagher that I am averse to "loose curls." I suggest a cheerful ponytail.

"Ponytails do not photograph well," she cautions, assuring me that she can do my hair down in a way that I'll like. "Good hold and volume are what make photos look polished," she says. "You do not have to look like Miss Universe."

As promised, the strands of my hair still move when she is finished, but they are tamer and shinier. At the crown, they have been just teased. Around my face, they are so smooth they are almost reflective.

"Generally, you want the front to be a little sleeker," she says. "Those pieces—from root to high cheekbone—should be smoother. Even if you're doing a curlier style, the curl should come in below eye level."

The Makeup

Armed with a good hair day, I refocus my attention and phone makeup artist Suzy Gerstein, who confirms that professional photographs necessitate a more substantial arsenal of cosmetic tools.

"The difference between doing your makeup for a photograph versus doing your makeup for a real-life event comes down to lighting," she tells me. "For photographs, we makeup artists take into account various lighting scenarios that may wash out or intensify one's features and adjust our makeup accordingly."

And while Gerstein cautions that applying too much product—"eyeliner, blush, bronzer, you name it"—is a greater misstep than applying too little, "a bit of well-applied makeup never hurt anybody."

I agree, which is why I swipe on an extra slick of FACE Stockholm Fresh Face Foundation on the morning of the shoot for good luck. A Gerstein devotee, I follow the rules: I cover a remorseless pimple on my forehead in Laura Mercier Secret Camouflage and "feather" in my eyebrows with a pencil that looks like dirty dishwater. It is a perfect match. As I have been trained, I fluff on an amiable eye shadow and add some shimmer for "dimension" from the Kjaer Weis Eye Show Compact (in "Cloud Nine") that Gerstein recommends, which looks like it was handcrafted for Judy Jetson. This thrills me.

After lining my eyes in Stila Stay All Day Waterproof Liquid Eye Liner, which wins me over when it does, in fact, stay all day, I tackle my lashes with a curler and swipe on two coats of black mascara. I tap on blush, lipstick, a dab of gloss, and Laura Mercier Secret Brightening Powder. I add translucent powder for the barest sheen and stand back to take it all in. The truth is I look like porcelain—luminous and polished.

I text Charlotte—the wizard who agreed to capture this for me—that I am all done. I am so done.

"Wow," Charlotte exclaims when she meets me at Bumble and bumble. "It's Picture Day!"

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Hellin Kay
The After!

The Picture-Taking Tips

Together, we evaluate windows and doorways and a sun-soaked chair, which at last wins. Charlotte starts to shoot the moment I sit down. I fidget a lot and struggle not to duck and hide, as is my impulse. When I retreat into my rib cage—very model-y, I think!, Charlotte tells me to pull my shoulders back.

"It feels unnatural and awkward," she says. "But it looks so much worse to be hunched over." I sit up straighter at once. After a few more clicks, she swipes a soggy umbrella from the salon floor: "Hold this."

"Hands are confusing," she explains. "When your body has no clue what to do with them, you stiffen up."

Charlotte snaps so many frames so fast that I have no time for pretense. I relax, letting my lips fall into an old shape. I smile.

"Got it," she whispers. "Pretty as a picture."