Caroline Issa is very busy. The Montreal-born entrepreneur is CEO and fashion director of quarterly style and culture publication Tank, editor-in-chief of online magazine Because and a creative consultant who has worked with some of the industry’s biggest names, from Mulberry to Chloé. She also has a killer dress sense.
In fact, so impeccable is Caroline’s personal aesthetic, she is a perennial street-style favourite and captivates fashion fans every show season with her signature polished yet playful look. She has also leant her style eye to collaborations with the likes of Monica Vinader and Nordstrom.
After living around the globe in her twenties, from Seattle to Texas to Singapore, Caroline has called London home for the past 20 years. It’s here where we catch up towards the end of the summer to discuss career pivots, new-season motivation and what makes a great power suit.
Your route into fashion wasn’t a typical one – you studied business then went into management consultancy. How did the pivot into the magazine world happen?
It was wholly unexpected and happened totally by chance. I was travelling around the world as a management consultant, working for soft-drink brands and banks. My world was full of grey, black and brown suits. A mutual friend introduced me to Masoud Golsorkhi, the co-founder of Tank. The magazine was already four years old and creating packaging and branding for the likes of Stella McCartney and Levi’s – incredible brands that I’d grown up with. I was intrigued by luxury fashion, and to get thrown into that very glamorous world was so exciting. It was the chance of a lifetime. Twenty years later, I haven’t looked back.
How do you find the balance between work and life outside the office?
I don’t think I did for a long time. You have to be very intentional about carving out time for yourself, and that hits for different people at different times. It’s only been in the last five years for me. My weekends are just as packed as my week: I love doing things, seeing things and reading things. But I’m intentional about making that time for feeding my creative and quiet soul. One has to actually put away the laptop and say, “I’m going to read five pages of my book tonight or listen to a podcast”. Sleep is also precious to me and I always aim for eight hours. It’s funny how in the ’90s, when I was growing up, everybody would brag about how little sleep they had the night before and how they stayed up partying. Now the brag is how much sleep you can get.
What’s the most valuable lesson you’ve learnt in business?
Having been through so many highs and lows, one of the lessons I’ve learnt is that reliance is the thing that gets you through. It’s about figuring out how to be even in the face of great celebration and despair and understanding that nothing is ever too great to overcome – there is a solution for everything.
I’ve learnt that reliance is the thing that gets you through. Nothing is ever too great to overcome.
What do you reach for when you need a confidence boost?
Which pieces are on your new-season wish list?
I have my eye on the patchwork pieces by Marine Serre and the Prada bombers from the AW22 runway collection, especially the ones with feathers. Emilia Wickstead does a mean dress and suit – she’s so good at old-school glamour. And feminine tweed pieces by Huishan Zhang. He does ladylike elegance in a modern way, which I appreciate.
Which products will we find in your everyday beauty kit?
I don’t do a lot of make-up, so my beauty kit is more focused on skincare. I invest in facials with Fatma Shaheen and I’m obsessed with her skincare line, Skin Design London, which does an amazing vitamin C serum. I’ve recently been using a night cream from Noble Panacea. It’s like food for your skin and really moisturising. I also use Charlotte Tilbury’s Magic Cream with SPF. Then I’ll use a Chanel mascara, and that’s it. If I knew how to do make-up I would – but I suppose that’s what TikTok tutorials are for!
What never fails to make you feel motivated?
Reading great writing, whether that’s a novel, a piece in The New Yorker or a Tank feature from an author I’ve commissioned. I have such respect for people who can articulate themselves and take nothing other than words and create vivid stories. That motivates me even more than visual stuff – it’s like true art. I’ve just finished reading three books by Jeanette Winterson, which to me are the pinnacle of creative genius.
What are you looking forward to in the season ahead?
I’m looking forward to forging deeper connections with people, be that with friends and family or, during fashion month, with people I haven’t seen for a long time. Even with acquaintances I would love to get to know better. The last few years have taught me that what excites me the most isn’t scanning a cocktail party and just saying hello and goodbye, but committing to connecting to others.
What was your connection to fashion growing up?
When I was 14, I was scouted to become a model. I was terrible – I was such an awkward, nerdy teen and too much of a control freak to really let go, but I had incredible opportunities. At 17, I spent the summer in Milan and got to do the Romeo Gigli show and the Calvin Klein showroom. It was really fun, but it was that experience that made me a feminist. It was the ’90s in Italy so I was looking out for every other model to make sure no one was taking advantage of them. After that, I decided I wanted to apply to university and get my business degree, so I quit.
You’ve almost come full circle having been in shoots for the likes of J.Crew, Monica Vinader, Emilia Wickstead – and, of course, been an ICONS cover star twice. How do you feel about being in front of the camera now?
It’s ironic that, 28 years later, I’m doing more modelling than ever. I’m still terrible at it but I appreciate it, and I think as you get older you become so much more comfortable in yourself. Now I can indulge in fashion and the creativity – it’s less pressure. I wish I could have told my 15-year-old self to loosen up and enjoy the glamour, but when you’re that young it’s hard. I have tried not to work with very young models throughout my career because I’ve seen so many dicey situations myself. It’s great to see model alliances really looking out for younger models now.
Your personal style is hugely coveted and regularly documented by street-style photographers. When did you start to cultivate your dress sense and how has it evolved over the years?
I always read fashion magazines and was clued up about designers – as a teen I bought shares in Donna Karan when it IPO’d. During university I loved vintage shopping and as soon as I could, I invested in beautiful pieces. When I got my first job as a management consultant and finally had financial independence, I invested in a brown trouser suit from Jil Sander. I still have it in my archive. Then I joined Tank and all of a sudden I could take off the shackles of boxy jackets and pencil skirts and start playing. My style hasn’t changed that much, but I’m becoming more experimental as I get older and have more confidence in what I do and therefore what I wear.
You have one of the busiest work schedules in the business. What’s your secret to staying organised?
I don’t know if I truthfully am. I’m insanely busy, but who isn’t? I have constant to-do lists and always feel like I’m a little bit behind. The good thing is that I enjoy the madness and I embrace being busy rather than being bored. I don’t like slow days and always find something to do with myself. But am I always on top of things? Absolutely not!
I’m becoming more experimental as I get older and have more confidence in what I do, and therefore what I wear.
What does a typical working day look like for you?
My working days are quite packed and always varied, which I love. I’m so grateful that fashion is constantly evolving and growing. It’s one industry where you can show up to the office and not know what’s going to happen that day. I might be sitting down to brainstorm ideas for the next issue, having a social-media meeting with the team, thinking about virtual reality with my programmer or talking to my accountant. Usually I wake up at 7.30am and have a cup of Yorkshire tea with milk. I’m not a morning person, so if I don’t have that tea, my day is off-kilter. I’ll also have a coffee in the office – they are my only rituals.
Navigating workwear can be tricky, but you always bring a sense of personal style to smart looks. What’s your approach to dressing for work?
It’s about embracing traditional pieces with something that adds a fun, fresh, confident twist to them. For example, the McQueen suit I’m wearing in this shoot has an unexpected cut, with pockets on an angle and in a bright red. Whether you’re a corporate lawyer, an accountant or a fashion journalist, it’s amazing to have the option of going confidently into a meeting wearing a red power suit.
Having seen what corporate workwear was like 25 years ago, and where it is now, there are so many more exciting options around colour, print, cut and shape. And it doesn’t have to be luxury. The high street has realised it can’t just offer brown, grey and black pant suits. There’s much more freedom.
What are your workwear staples?
A crisp white blouse, a silk shirt and a trouser suit that can be separated or worn together. I also love pleated skirts. They’re an unexpected thing to talk about in regard to workwear, but they are so useful worn with a blouse and a belt or a silk T-shirt. I used to wear heels, but I’m definitely loving flats right now, and I’m all about penny loafers. I don’t really do sneakers, but I have just bought a pair to try.
Which brands do you look to for polished pieces that last?
I wear Racil suits and a lot of double-breasted jackets from Gucci; the cut and detail is amazing. I’ve invested in Maria Grazia Chiuri for Dior ‘New Look’ jackets which are so flattering with any trouser or skirt underneath. And Prada for boxy pieces and great trousers that I can pair with any jacket. Italian label Plan C does incredible blazers with unexpected details such as little ribbons.
What is your all-time best investment buy?
I have a collection of Prada print dresses from pre and commercial collections that I wear all the time, every year. They’re completely flattering and look good with a blazer or a sweater – they’re so versatile.
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