The Secret Confessions of Taylor Swift’s Instagram Photographer

The person* behind the cameraphone speaks.

Katie Simpson
The Hairpin
7 min readMay 25, 2017

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Source: Instagram

None of this would’ve happened if I hadn’t adopted a cat. Well, if I hadn’t adopted a cat and then taken a dozen photos of it. But I’m getting ahead of myself.

The idea of becoming Taylor Swift’s Instagram photographer started at the Victoria Secret Fashion show of 2014. Shadow was just 20 weeks old, and I’d left him alone for the first time to photograph the event. I was waiting in line in the bathroom when I pulled up the three-week-old Instagram account I’d made for Shadow (@the_nights_meow).

I heard her before I saw her. Taylor cooed awkwardly from behind me, almost looming with her lanky frame in five inches heels, little wings sprouting from each heel. I knew she was tall but with her heels, her lips were at perfect level with my eyes. If she swayed the wrong way she could’ve rouged my eyelids.

“These are so good!” She kept cooing. “You don’t mind if I uh,” she leaned towards me and started to scroll through the photos. She said they reminded her of Meredith as a kitten, but you know, way darker. I smiled, pretending to know who Meredith was. I kept wondering if her nails, filed sharper than a vampire’s fangs, could ruin my iPhone screen.

When the bathroom door opened. I nodded for her to go first, ready to tuck this away as a crazy celebrity story. But when I left the bathroom, the door collided with her pointed nails. Taylor began talking before I even had a chance to apologize. “I know this is crazy, but I have these, like, crazy good vibes about you and your photos. I have this idea, Can you call my executive assistant’s number on Tuesday?”

Source: Instagram

I tried to smile, while taking the card. It was red like her signature lipstick, and nails, so perfect her nails would’ve blended into the card if it weren’t for her skin. It only had a first name, Emma, with three emoji icons: a pen, a phone, and a knife. The clearest part was a phone number at the bottom. I looked up, more confused than ever, but Taylor was already teetering away.

To avoid bad Hollywood karma, I called Emma. Taylor wanted me to go with her and the band HAIM to Maui in January. They didn’t want a session — that was so Cindy Crawford in 1995. This was almost 2015, they needed someone who knew how to do off-the-cuff photos. Socially authentic but polished enough for the fans.

Obviously, I’d be paid for my time and expenses. I didn’t need equipment: they had both iPhone and Android phones, stands, and flash equipment specific to each. Oh, and if I wasn’t comfortable with phone photo editing, I needed to get used to these 12 apps they used before January. With all this in mind, would I be interested?

I had hung up the phone before I realized I’d said yes.

Working with Taylor was a strange mix of intimacy and professionalism. After all, I had to watch her daily life for the perfect shot. Was it early morning in the Suburban as she sat half awake drinking coffee? Or was it making bubbles as she cleaned her dishes at night? She said she loved feeling so regular washing dishes. But having red rubber gloves, based off a 1962 design tailored to fit her enormous hands couldn’t have hurt.

Source: daily mail

The first night in Maui, Taylor wanted a girls’ sleepover to get everyone comfortable with me around. “My Instagram has to paint this picture. it needs to have this feeling, real but finished, you know?” She’d say that multiple times, but that might’ve been the only time she did it while wearing a 14-karat gold face mask.

Getting that idea was work. Like the photo of all four girls wearing matching Bill Murray shirts. Getting this shot required a two-foot-tall stool for just the right angle, while carrying all four purses as the girls tried different poses for 15 minutes. Reducing blur was hard: their phones kept vibrating, shaking my arms.

Source: Instagram

The work to get an image just right was also a post production hand-holding process. I spent more of my time listening to Taylor agonize over different photos than actually taking or editing them. One night, she was up pacing in my hotel room. It was 1 a.m. but she couldn’t sleep. Should she post her chasing a chicken on Kauai or all four girls on the hike? I sat there, working to listen to her concerns, even though I was struggling from jetlag and my own pounding headache.

After Maui, I graduated from merely a photographer to an on-call Instagram visual advisor. Soon, I would get photo batches weekly, asking for an hour to pick my three favorite shots. Should Taylor go with the shot of her eating french fries with Selena Gomez? Or, should she go with them walking, arm in arm, perfectly under the McDonald’s arch? How did people feel about McDonalds these days? Could someone in marketing pull that data? Suddenly, I was being paid as a ‘visual curator’, making a retainer as part of this covert Instagram committee. We spent hours trying to walk this line, mixing McDonald’s ice cream with Jimmy Choos, all while looking effortless.

Source: Instagram

Despite the fancy title, Taylor still wanted me there for some of her down time with friends. I was being flown from New York to LA at least once a month on her private jet, often with her cats and their professional cat sitters. I was there, an iPhone and Android in hand, to watch models get drunk on sugar and butter for Camila’s birthday. I was the one getting everyone placed for the infamous vegan cookout photo.

I wish I still had the photos from that event. I can still remember the group shot where Taylor and Calvin revealed their relationship. Everyone acted surprised but their eyes didn’t quite go wide enough. At the back, Selena was rolling her eyes. This photo wasn’t even up for discussion. Instead, it was lost in our daily ritual of wiping the photo phones for security purposes.

Source: Instagram

Of course, everyone wants to know what it was like, seeing her relationships up close. Was it full of fights and drama, like music video for “Blank Space?” Or was it more secretive like “Wildest Dream?” Well, I never saw any cars attacked with golf clubs or lions roaming outside her place.

If anything, they knew better how to perform a relationship on stage than off. Nothing solved a fight as well as leaving a club in the glare of paparazzi lights. Swan goals? They’d just had a drunken fight over who would get to use the swan floaty. Taylor had clung on to the back using her legs. Calvin wasn’t exploring, he was trying to find a way off the float. When the pun ‘swan goals’ came up, they both started to laugh, the fight fading in the heat and alcohol.

Source: NY daily news

Sometimes, they used them to remember why they were together. I was there for Taylor and Calvin’s one-year anniversary. The popped-foot kiss photo was my idea. She flung her foot a little too hard and the sand backlash nearly scratched my cornea. Despite the fact that they were barely speaking before the shoot, they at least agreed to share one three-room suite that night.

Was I shocked when they broke up? Not really, but her relationships were never my job. She had a romance specialist on retainer for those issues back in NYC. I was only there to help preserve the moment and add the right filter.

Working with Taylor was what I loved and hated most about photography. She understood the power of image and persona like so few people. But, I couldn’t keep working on it forever. I was tired of 6-hour flights and dealing with models crashing from sugar and sobbing about weight gain. Plus, my cat’s Instagram hadn’t been updated in almost a year. When Taylor heard that, she completely understood. It’s hard being a working cat mom.

*This is a piece of satire, you guys.

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Katie Simpson
The Hairpin

Astrologer, Cat mom, big heart, old soul. Fuel my caffeine addiction http://paypal.me/KS1989