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Why Every Woman Should Do A Pinup Photo Shoot

Why Every Woman Should Do A Pinup Photo Shoot:

“Bust out!” the photographer said. “Core in! Butt out! Smile!”

I struggled to arch my back in a way that might vaguely resemble “sexy.” I smiled and realized I had lipstick on my teeth. I tried to suck in my stomach, a seemingly impossible task. I hoped my underpants weren’t riding up in an unattractive fashion. I teetered on high heels. I concentrated hard on looking hot.

And then I lost my balance, tipping over before catching myself.

“Shit,” I said to the photographer, Carol. “Modeling is hard work.”

I never thought I’d find myself in a stranger’s house in Los Angeles, posing for photographs in my underwear and high heels. But life is full of wonderful surprises, isn’t it?


A few weeks prior, my friend had posted photographs of herself looking particularly fetching in a retro bathing suit, laying on a bed with her legs up against the wall. The photos were clearly a professional job, with excellent hair and makeup and lighting. But the thing that struck me the most was how happy she looked in them.

It occurred to me that I hadn’t felt as happy as she looked in — well, in a little while.

Oh, I had lovely friends and family and I enjoyed my life as a writer. I even had a cool puppy. But I didn’t feel great in my own skin, particularly since I’d gained weight after leaving the walking-friendly city of New York for the car-choked and surprisingly donut-packed environs of Los Angeles. In fact I weighed more than I’d ever weighed in my entire life.

I’m a sex-positive, body-positive, fun-loving feminist. I know I’m supposed to love myself at any size and cherish my own beauty and all that jazz, and I strive to be proud of who I am. But the truth is that like most folks, I’m far more accepting of others’ bodies than I am of my own. So while I would’ve genuinely encouraged any girlfriend of any size to give modeling a try, I was feeling a little too hefty to “deserve” such a fun thing. It’s a fucked-up way to view a situation but then, like a lot of people – women and men – I’m fucked up when it comes to my view of my own body. Anyway, I was wrestling with all that self-esteem crap, and it was beginning to wear me out.

You wouldn’t think it’d be the ideal time to do a photoshoot.

But my friend looked so thrilled by the whole experience, and when I asked her about it she gushed that I had to try it.

“Everyone should do it,” she said. “It’s these two women, Carol and Stacy. Carol is the photographer and Stacy does hair and makeup. They shoot in this cool house and they have props and they coach you. You feel just like an old-fashioned movie star. And there’s a Groupon deal.”

“Well, if there’s a Groupon deal,” I said.

I thought I might as well give it a try. After all, I would just be wearing a series of cute dresses, not showing a lot of skin. Who doesn’t love a cute dress? Plus, I trusted that the makeup and hair woman would make me look pretty enough.

In fact, maybe we could just do headshots. A pin-up from the neck up. That sounded pretty good to me. I’m a comedian and an author, and I often need a headshot for one thing or another. I could justify my fear of showing my whole body by saying it was an excuse to get a foxy new book jacket photo.

So I bought the Groupon deal. I scheduled my time and told all my friends I was going to do a retro pin-up photo shoot with Iconic Pinups, and that the next time they saw a photo of me, I’d look like something right out of the 1950s. I picked out my dresses very carefully.

Then I got to the set, a retro, kitschy midcentury modern home in Los Angeles. And after the very talented makeup and hair artist, Stacey Lande, did her magic, the photographer, Carol Sheridan, watched thoughtfully as I stripped down to my skivvies. It wasn’t a lascivious look, but rather the analytical eye of an expert evaluating a potential project.

“Did you want to do a lingerie shoot?” she asked.

“Oh no,” I said. “I mean, I have all these tasteful dresses.”

“But we could try a lingerie shoot,” she said.

“I mean, I’ve got navy blue underpants and a black bra,” I said, stalling for time. “So it doesn’t match. So that’d look weird.”

“It’ll look fine on camera,” she said.

I wanted to say yes. But I didn’t have the “right” kind of body to put on display…or so I thought.

“And you can wear a little robe,” Carol added. “We have cute ones.”

“Well, if there’s a robe,” I said, and that was that.

Fuck it, I thought. It’s not like I’m ever going to show these to anybody.

I should note that I didn’t feel pressured one bit. It was more like she had noticed a desire that I had and was gently coaxing it out of me.

Of course, it took a little while for that part of me to actually show itself.

In the first photo Carol snapped, I looked like I was trying to disappear into the wall.

Sara Benincasa pinup First Photo

But then I started to relax.

Sara Benincasa pinup SECOND PHOTO

Carol goofed around and made me laugh.

Sara Benincasa pinup THIRD PHOTO

And that’s when things got really fun.

Sara Benincasa pinup FOURTH PHOTO

I finally put on some real clothes — sort of.

Sara Benincasa pinup FIFTH PHOTO

I mean, who doesn’t love a rotary phone?

Carol taught me some classic pin-up poses, like the aforementioned “legs up the wall and kind of twisted but you pretend it doesn’t feel weird” pose.

Sara Benincasa pinup SIXTH PHOTO

And the classic “pretend you’re laughing so that it looks like you’re having a spontaneous orgasm” look.

Sara Benincasa pinup SEVENTH PHOTO

By the end of the shoot, I’d had so much damned fun I’d forgotten my weight, my height, my BMI, and how many calories I’d taken in that day. I’d forgotten my earlier awkwardness and my reticence to pose in my panties and bra. I’d forgotten to hate myself for having a perfectly normal body. I’d forgotten everything but the thrill of embodying the classic, sultry archetype of the pin-up girl.

When we sat down after the shoot to pick out the best images, I was shocked. I couldn’t believe I looked like that. It wasn’t that they’d magically made me look skinny or “perfect” in the eyes of Hollywood or something. No one would mistake these images for, say, Brooklyn Decker. But I looked good. Like, really good. I looked pretty. And best of all, I felt good when I looked at those photographs.

I still feel good about them. And by extension, I feel better about myself. It’s not that I’ve undergone a radical transformation or something. I’m the same weight, although I’m eating much better and walking much more. I have the same nose and the same eyes and the same skin.

But something happened in that little house in Los Angeles, in front of that camera and those lights and that photographer. I felt transformed. And even when the makeup came off and the hairspray washed out and I put on sweatpants and sat on the couch to watch Bar Rescue, I still felt changed in a good way.

In other words, a good pin-up photo shoot is its own kind of magic.

So ladies, go get yourself did up real pretty for a photo shoot. Bring a girl friend. Make a day of it. And gentlemen, consider offering such a photo-shoot to your favorite gal this holiday season. She may not seem like that type of girl, but you never know. With a little encouragement (read: not pressure), she may warm up to the idea and have the time of her life. And then you get to have the fun of looking at the pictures (and I have been led by my gentleman caller to believe it is quite fun, indeed).

Now here’s me, before and after. Dead sexy, I know.

Sara Benincasa pinup EIGHTH PHOTO

If you don’t like any of these photos, that’s alright by me. In the end, while I’ve greatly enjoyed sharing them, I’ve realized they weren’t actually for anybody else but me.

And as my own worst critic, I have to say: I look fucking awesome.


Sara Benincasa is a comedian and the author of Great and Agorafabulous!: Dispatches From My Bedroom. She tweets @sarajbenincasa and is currently on tour: dates are at SaraBenincasa.com/shows.

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