In the fashion world, we’re lucky that we have so many successful women to look up to and whose careers can guide us. From big names like Anna Wintour and Jenna Lyons to lesser-known ones (though no less inspiring), there’s no shortage of female power. And high up on the list of women to admire, there’s Caroline Issa.
There is perhaps no other individual currently working in fashion who has seen the industry from as many angles as the Canada-born Issa has. She began with a modeling gig in Milan, became a management consultant for retail and consumer brands, and is now the chief executive and fashion director for Tank magazine. Oh, and she also happens to be one of the most photographed street style stars in the world—and she just launched her own line at Nordstrom. Busy much? Well, she’s not too busy to share what she’s learned throughout her 16 years in the business. We caught up with her and picked her brilliant mind about everything from childhood dreams to being a female entrepreneur.
Keep scrolling to learn from the master!
After three years working as a management consultant in London, I started thinking it’s time for me to do something else. I spent evenings and weekends getting to know people I respected, and getting to know the industry at large. I think for people who want to get into fashion, you have to develop a point of view, and you do it by getting to know people in the fashion industry. Surround yourself with the people you want to start working with. Whether you’re just giving a helping hand, or doing extra evenings and weekends, experience it as much as you can. I was super-passionate about my job, and I loved the people I was working with. You just have to soak it all in. Go to fashion talks. Try to get as much work experience as you can. Really immerse yourself in it.
I wouldn’t do anything differently. I’ve been incredibly lucky that I’ve gotten to experience so many different aspects of this business. I haven’t had a traditional trajectory, but I feel like every experience builds on another, taking risks pays off, and I definitely wouldn’t do anything over again.
If I could give one piece of advice to my 17-year-old self, I think I would assure her that everything will work out. The huge nervousness, the huge ambition, the terrifying sense of the big void—it will all be fine and it will all work out. Just keep doing the things you’re passionate about, that interest you the most, and it will work out.
The fashion industry is one industry where there are a lot of women, but when I was a management consultant I worked on a mostly male team. I was definitely very concerned with making sure there was great representation for women in a male-dominated environment. I learned very early on how to hold yourself in an all-male environment. We’re lucky in the fashion world that there are so many role models for women. You just have to look at DVF, Jenna Lyons, and Anna Wintour (among others), and you know that women have a lot to offer.
As a business owner, in equal measure there are low lows and high highs. It’s always challenging, but the benefits definitely outweigh the negatives. It’s just 24/7 that you’re constantly thinking about ways to manage your business and your team, making sure you develop in the right direction. If you don’t love it, you can’t do it.
I think it’s important to wear things that you feel 100 percent confident in, whether that’s in a colorful suit or a gray or black suit, or a great pair of slacks and a sweater. For me, the key to having great style is just feeling comfortable and confident, no matter what you wear. After that, you’re set.
Nordstrom Signature and Caroline Issa Stripe Cashmere Sweater ($445)
Nordstrom Signature and Caroline Issa Double Face Cocoon Dress ($1,495)
Nordstrom Signature and Caroline Issa Classic Pinstripe Shirt ($395)
Nordstrom Signature Textured Oversized Cashmere Cardigan ($825)
Nordstrom Signature and Caroline Issa Geo Print Wool & Silk Jacket ($895)
Nordstrom Signature and Caroline Issa Double Face Leather Jacket ($2,995)
Nordstrom Signature and Caroline Issa Leather Biker Jacket ($1,595)
What do you think you learned from Issa’s career tips? Tell us in the comments below! And keep reading for eight more things you need to know if you want to work in fashion.