Rosemary Mac Cabe

Hemlines, heels and haute couture – your daily dose

Brunch with Caroline Issa, fashion entrepreneur

Caroline Issa is a fashion director and editor, as well as modelling in a J Crew lookbook and, now, designing a line of shoes and handbags for LK Bennett. But she started out in management consultancy. Over brunch, I met one of the fashion world’s most photographed women and asked her, well, a whole host of things.

Mon, Apr 8, 2013, 07:30


If, like me, you’re clued into the world of street-style photography, you’ll know who Caroline Issa is. Despite all of my internet stalking, however, I wasn’t altogether prepared for brunch – in Avoca, of course – with Issa. Meeting to chat with Issa about the launch of her collaboration with LK Bennett, I was expecting some fanfare, perhaps a smidgen of diva-ish behaviour, some salad-picking and a lot of careful answers.

What I got, instead, was a really lovely two-hour chat with a woman who felt like a friend. She ate pate, if you’re interested; she chatted about her life, about fashion, about that Suzy Menkes piece and about shoes (not just LK Bennett’s), for as long as she was allowed. Here’s what we talked about . . .

Did you have any worries about getting involved with designing?

I think I was initially nervous, definitely, because I’ve never designed anything. But at the same time, the reason I decided to take the opportunity was because I knew that I had a really strong point of view and I love taking on new challenges, and initially I was sketching my shoes out. And I’m not the best drawer, but after a while you get to a point where they look okay, and so I was able to show sketches of exactly what I wanted that were incredibly detailed. Detailed enough that the shoes I have today are very, very, very close to the sketches I had. So even though I’d never designed anything, I felt that actually I had a really strong image in my head of what I wanted – so because of that it came out rather naturally.

Has it changed how you shop for shoes?

No – I think I still gravitate towards styles . . . I love a great pointy shoe. I’m probably more amenable to a kitten heel now than I used to be, and I think actually I was wearing LK Bennett kitten heels maybe a year before I was approached for the project, so it was a nice natural fit. My aesthetics are still the same. I’m not a clunky platform type of woman, so you still stick to your style and what it is that you love. But certainly I have a big appreciation for all kinds of shoes, how they’re constructed. And I understand the pain of making a shoe for a certain price point, whether it’s my style or not.

What are your favourite shops on the high street?

Whistles – is that considered the high street? I would definitely say Whistles, Cos, I’m a huge J Crew fan. LK Bennett is sort of kind of in that affordable luxury, not-quite-high-street, not-quite-luxury, and obviously I shop there. But I would say Cos and Whistles, and J Crew in the US, but they are coming to the UK.

What would you pack for a weekend break?

I love denim – I’m wearing J Crew cords now and I live in them. I live in Equipment blouses, so I would probably bring … and I love denim blouses, so I’d probably wear the cowboy uniform, double denim, and little jackets. My weekend wardrobe is typically super simple – I do a lot of trousers and shirts, a lot of leather biker jackets, things you can throw together. It’s easy – you don’t have to think about it.

What’s in your ultimate capsule wardrobe?

J Crew cashmere sweaters, a Tom Ford coat – this is my ultimate, right? – a Lanvin dress to go away, T-shirts, the perfect white T-shirt and the perfect black T-shirt – actually Sunspel is doing these beautifully soft cotton T-shirts – and a great pair of flats and a pair of stilettoes.

You went from a career in business to a career in fashion – how did that happen?

I’m Canadian and I went to university in the US and I studied strategic management and finance. When I graduated I became a management consultant, and my first job was Nordstrom, and I was working on the petite and plus size division of Nordstrom.

But before I went to college I had modelled, and I discovered that I loved the world of fashion but I was a bad, bad model. And I decided that if I went back into fashion I wanted to have a point of view that was, first and foremost, listened to. As a model you’re slotted into someone else’s vision.

So then I moved to London and I was doing corporate strategy work for Boots, and I met the manager of this niche magazine, Tank, in London – and it was kind of the right place and the right time. He was looking for someone to help him run Tank, so I gave up my really stable, well paid job as a management consultant, much to my parents’ horror, and became a fashion publisher and entrepreneur, and it was the best decision I’ve ever made.

It took me a good two years to really understand the landscape of fashion and fashion publishing, of how the industry works, and there were many moments when I thought, what have I decided to take on? But it was always overtaken by the fact that I wake up excited to go to work. I love what I do – I don’t find it’s work. I’m so lucky in that sense that I’m really passionate about what I do, and I think that’s a factor of working with the people I work with but I also love the fashion industry. It’s fun, fantastic, critical to the economy. And it’s an interesting business alongside being incredibly creative.

The ‘Parrot’ shoes, by Caroline Issa for LK Bennett

What are the best and worst parts of the fashion industry?

I just finished a month of travelling for fashion weeks, I did New York, Milan, Paris and London, and when you’re sitting at a fashion show and you come out feeling like you’ve just experienced something you’ll never see again – an incredible show with this creativity that’s channelled into cloth. Every time that happens, I think, this is why I’m in the business. Everything comes together – commerce and creativity and the people around it.

The worst about the industry is … for something that’s fast, it’s still quite old-fashioned in the way that it approaches digital, multi-ethnicity in the mass media, and also some of the supply chain issues when it comes to fast fashion can be really detrimental. So there are still obviously issues, but that’s every single industry. There’s still a lot of work to be done to make sure it’s all inclusive, sustainable and fair.

Tell me about Susy Menkes’ Circus of Fashion . . . as someone who is photographed a lot, what did you think about the piece [in which Menkes talks about the peacocks – the people outside the fashion shows who become a show in and of themselves – and laments the passing of the good ol' days, when editors wore black and anyway, no one cared]?

A lot of what she had to say is very valid. Going to a fashion show during fashion week has completely changed. The number of cameras outside a show is so numerous and overwhelming, that it’s a different experience to when I started, 11 years ago. And there is a layer where there is a certain amount of, as she put it, peacocking outside the shows.

But at the same time I think she was really wrong in her statement in terms of saying that she wants to go back to the good old days, because you can’t. The industry has changed completely, and all we can do is look forward, and try to leverage what all of this means.

So I totally agree with her in that it’s so completely different, but it’s irrevocably different, and you can’t go back to the way it used to be when fashion editors only wore black and weren’t photographed. We have to figure out what it means going forward. How does live streaming work? What is the place of blogs next to journalism? And the ideas of critics and criticism in a whole spectrum of opinion. There were so many questions that nobody can answer. It was interesting that she put it down on paper. It was definitely one of the biggest talked about things during fashion month, everybody, traditional and new media, was talking about it.

Has the rise of street-style photography changed how you dress for shows?

I’d be lying if I said no. It hasn’t changed my style, but it’s definitely changed how much time I spend thinking about what I’m going to pack and putting outfits together. In the beginning, you always want to present an image of yourself that you’re happy to put out to your contemporaries, but now there’s an extra layer of, these pictures get beamed across the world on the internet. I probably put more thought into how I put outfits together than I used to, but it hasn’t changed how I dress in general.

Who gave you the “wow” moments this season?

The Céline show was amazing, where you came out feeling like the confluence of the mood, the clothes, the girls, the hair, the make-up, was amazing. Proenza Schouler in New York was amazing. The Dior show, in terms of production value and what Raf [Simons] is doing with the clothes. And the [Louis] Vuitton show, seeing Kate Moss coming out, that’s always an a-ha moment. The Prada show is my favourite every season. It’s essentially like going to the theatre 12 times a day for four weeks, and there are some things that stick in your mind more than others.

Of young designers, who would be your picks?

I’m a huge fan of Simone Rocha and JW Anderson. Barbara Casasola in London, who’s Brazilian and got her training in Milan, does incredible dresses. Matthew Harding and Levi Palmer [palmer//harding], two guys who do white shirts, that’s all they do.

You’ve done business, magazines, shoes – anything else on your to-do list?

In life, yes, millions, but it’s all been very organic. Last year I was the face of J Crew, which I loved doing because I was such a customer of theirs and I love what they’re doing as well. So things just come up naturally – I would not have been able to predict, five years ago, that all of these things would happen. So I have no idea what the next five years hold.

What are the biggest mistakes people make when getting dressed?

I guess, leaving the house not feeling comfortable in whatever outfit you’ve planned. There’s nothing worse than feeling not quite right in your own skin, and I think people just should stay true to themselves and their own style and feel 100 per cent confident in their own skin, it doesn’t matter how you put an outfit together or whether you’re following or breaking rules. The biggest mistake is thinking that there are rules in fashion you need to follow. As long as you feel super confident in whatever it is you’re wearing, you’re golden.