How I got Taylor Swift to go to work for me.

And she more than delivered. Settle in for some great Glamour memories.

Taylor Swift photographed by Damon Baker, styled by Natalie Hartley, wearing Valentino. Make-up by Lorrie Turk. Hair by Jemma Muradian.

I’ve just realised this is my 100th post on Substack! Thank you so much for joining me here, gang, your support and feedback means everything to me. If there’s one thing I do miss from magazines, it’s speaking to readers, so the fact that I get do that here is wonderful. So, today I’m in the mood to revisit The Making Of an old Glamour cover.

And I can’t think of a better issue than this, the special one guest edited by the one and only Taylor Swift. Taylor Fricking Swift, you guys! I remember it fondly because everyone - including Taylor Swift - told me it wouldn’t happen. And somehow we all put in enough sweat and it did.

After months (and months) of asking, we were granted a shoot date in February 2015, when she was in London for The Brits. Already wildly successful and very famous for being a country music star, she’d released her first pop album, 1989, in October 2014 and that made her a giant of mainstream music. She’d never been more popular - although somehow she’s even more famous and popular now, 10 years later - so I was thrilled that Glamour was chosen as the magazine to promote her upcoming UK tour. 

The shoot date, a Monday morning, also happened to be my birthday - and a busy day in the London Fashion Week schedule - which I took as a good omen. Rookie mistake. Because I was soon being treated to a weekend of hell: the shoot was cancelled at one point - around midnight on the Saturday night - because Taylor’s management and the agent for our chosen photographer (the very talented Damon Baker) were having a minor scrap over a photo usage contract. I was so angry and stressed about it that I got a migraine, which probably explains why I can’t really remember the ins and outs of it. But I do remember sending a barrage of shitty emails to the agent and begging Damon to just please somehow find a way through.

They did. The shoot was back on. Frankly, we needed Taylor more than she needed us, and Elle magazine would have happily stepped into the breech if Glamour fell through. So her team was always going to win. Squabbles about future usage of the pictures was something I gave no shits about, frankly, and I knew arguing about it with the management of such a powerful celebrity was just pointless.

All fine in the end - just one of the many, many things that most people would never know happens behind the scenes and regularly derails the actual job at hand: making a magazine.

I was the last to arrive at the early morning shoot (there was always very little point in my presence until there were photos to examine) and Taylor had been the first. Let me stress: It is highly irregular for celebrities to arrive on time, let alone ahead of schedule. I said hello and Taylor’s first words to me that morning were, ‘Oh wow I love your dress!’ I’d met her a few times by this point and I noticed her opening greeting is almost always a compliment. She’s done the same to my daughter (‘That braid is so cute on you!’). I think it speaks well of her that she can scan a person for a split second and come out with something nice to say.

While she sat quietly having her make-up done, I set myself to work on the main reason I wanted to be at the shoot. No, not to get a selfie with Taylor (although, you know, rude not to).

But to try and persuade her to be our cover star on the issue and our ‘guest editor’. We hadn’t had a guest editor of the magazine since Teri Hatcher, at the height of her Desperate Housewives fame, in 2007.

Teri Hatcher photographed by Robert Erdmann.

I knew it was a long shot, to get the busiest pop star in the world to commit to even more work, but God loves a trier, right?  

In the weeks before the shoot, I galvanised the Glamour team for this mission. The way to get a ‘yes’ from busy, famous people, is to convince them that what you’re asking of them is not really much work. Once they or their team get even the tiniest whiff of ‘ball ache’, it’s game over.  

So the team and I thought of about half a dozen features we thought could be written by Taylor - feelgood stuff about her, her philosophies, her inspirations, friendship groups, stuff like that. (I wanted to strike the balance between having a nice presence of Taylor throughout the issue, but balanced with all the content Glamour readers would still expect to see.)

We then designed them all to a publishable standard - fully mocked-up pages with all the headlines and intros written, pictures in situ. At the top of each page I wrote a few short lines ‘selling’ why I thought this was a good subject for Taylor, how many words would be required to fill the page. We made every page look ‘broken up’ so there was no feature which required her to write any kind of lengthy essay. It was very much ‘listy’ ideas that required a few paragraphs from her. I wanted it to look as doable as possible. I suggested, if she didn’t have time to sit and write, she could have these subjects interviewed out of her, written up and sent back to her for approval. Or, she could simply send us voice notes (I already knew she was big on these for songwriting collaborations) and we could craft those into features for her approval. So, not really ‘no’ work for Taylor, but spoon fed as much as I could to make it easy.

How many did she get right?

I put all of these pages in plastic sleeves in a folder and at first presented them to her formidable publicist, Tree Paine. Tree is almost as famous as her superstar client these days. A lot has been written about her and what some see as her darkly genius manoeuvres on Taylor’s behalf. You won’t be surprised to know that I’m a big fan. I’ve always found her direct and honest about what Taylor will/won’t can/can’t do for me. And responsive with it. 

As I thumbed through the plastic sleeves of wonder for Tree and Taylor’s UK publicist, Kate Head, the response was an instant ‘no.’ ‘I do like the idea,’ said Tree.. ‘I just cannot see how she’d have the time.’ As hopeful as I was, I knew this was the most likely answer, but I figured, we’re here for a few hours together, I’ll just keep talking about it. I said I understood, totally, but I couldn’t resist trying because I’d just got so excited about doing something so different, and something Taylor had not done before. I let that sit with her and she said, ‘OK, I’ll show it to her, and see what she says.’ Which she dutifully did, on the spot. 

They both loved our little pages. Taylor said the same thing as Tree. ‘It would be fun, but I can’t see how I’ll have the time.’ 

Then Tree threw me a massive curveball. ‘Jo, I know we said we’d do an interview in a few weeks’ time, but we’re all here now - would you just do the interview with Taylor today?’

I couldn’t really say no. I had planned to get one of our star interviewers on it - I’m OK but I’m self aware enough to know I’m not the best. Entertainment director James Williams and I spent a panicky half an hour pooling questions and off I went. (She said a lot about the media ruining any chance she had of having romantic relationships, and that she wasn’t even interested in men right now. That night she went to The Brits and met Calvin Harris and had a whirlwind romance with him. )

By the time the shoot wrapped, Tree was saying she’d let me know if they had time for the extra pieces of guest editing work. I interpreted that as politely letting me down. Three weeks later, I was suddenly inundated with eight emails of copy from Taylor. No word beforehand, no earlier ‘Great news! She can do it!’ email. Just suddenly all this stuff arrived and it was exactly what I’d asked for. I thanked Tree and Kate profusely. ‘She started writing on a plane trip and then got really into it. She’s loved doing it, so thank you!’

It turns out, that my scrapbook had impressed Tree. Apparently another magazine moaned that they’d have loved to have Taylor as a guest editor and Tree told them, ‘Well, you didn’t show me a folder of prepared pages like Glamour did!’ Forgive me, but that thrilled me a lot because I know it was annoying for the team to have a ton of extra work that could well have turned out to be pointless.  

Looking back now, though, should I have put this photo on the cover instead?

I understand why often people were cynical about these ‘guest editor’ gimmicks. Often a celebrity is labelled as such and actually it’s all smoke a mirrors and they’ve just pretended they came into the office and worked on the pages with the team. But Taylor really did do all the work on it we’d asked of her, which, considering that she genuinely was insanely busy and didn’t have to, was amazing.

Taylor is super talented, she puts on an amazing show (hurry up June 2024!), and she takes no shit. She’s ambitious, she is proud of her power and she loves herself. And I love how that’s enough to enrage the haters. I’ve seen, many times, how brilliant she is with her fans. And even if you want to be a cynic and say it’s all an act, well, it’s an ‘act’ that I’ve seen bring real joy to those being treated to it. We have the strangest thing in common in having both been apologised to by Kanye West.

In short, I bloody love Taylor Swift. And not just because she once wrote half my magazine for me. 

Although she had nothing to do with this headline and picture treatment, which I’d forgotten all about and it just made me laugh all over again:

I think the fact that none of the higher ups said anything to me about this printing this picture, of an incrdibly explicit scene from Girls, might be the proof that they’d stopped reading Glamour??