Today we’d like to introduce you to Jessy Cain.
Born and raised in Los Angeles, Jessy has developed a thriving career in the fashion industry. While obtaining her BA in Communications and Marketing, she designed an accessory line that sold in boutiques nationwide. Jessy’s interest in fashion continued as a designer for Calleen Cordero’s eponymous handbag and footwear line, where she also took an in-house public relations position.
During her time with Cordero, Jessy began assisting one of Hollywood’s top stylists, Simone Harouche, whose clients include Miley Cyrus, Christina Aguilera, Demi Lovato, and Nicole Richie. After three years of assisting, Jessy was approached by Cyrus to join her Bangerz World Tour. Alongside Harouche, she collaborated with designers Marc Jacobs, Roberto Cavalli, Kenzo, Pucci, Jeremy Scott, The Blonds, and Bob Mackie to create custom looks and costumes for Cyrus’s dynamic performances.
Jessy’s clientele consists of an extensive range of fashion, beauty, commercial brands as well as personal shopping. She works with celebrities Sofia Carson, Arielle Kebbel, Stella Maeve, and Vanessa Bayer and top companies such as Sephora, Mink Pink, Ipekyol, Buick and The Honest Company. Her work is featured in major publications, red carpet events, television and is currently represented by The Wall Group agency.
In addition to styling, Jessy curates a blog to give fashion enthusiasts an inside look on her styling projects, personal ensembles #WhatJessysWearing and much more.
Has it been a smooth road?
Breaking out on your own is a giant leap for any freelancer but it’s a chance one has to take in order to further your career. For me, the first year was challenging because I didn’t have consistent work like I use to, which made me anxious and frustrated. But I learned to use that time wisely, by building my portfolio, updating my website and enjoy my time off. I learned more about myself and how to manage the work / life balance. But I’ve always been one to hustle and I also tend to work better under pressure. What else can I say, that’s the life of a stylist!
Is there some part of you work that is particularly difficult?
I think the most challenging part of my job has to do with timing. Sometimes, as a stylist, jobs get throw at you very last minute and if it’s a project I feel passionate about, I’ll do everything in my power to make it happen. However, the prep time can be 24 hours before a fitting or shoot which can be a bit nerve-racking. But if you’re not the type to thrive under pressure, then being a stylist isn’t for you.
How do you define success?
My definition of being successful is having the ability to pick and choose the jobs you want to do and creating the projects or stories you want to share. When a client comes to you asking what you envision and are open to collaborating with-out micromanaging, that’s when you know you’ve broken the seal of being a “stylist” to being a creative director. Another marker is, of course, budget. The bigger the budget the more freedom.
So, what’s next? Any big plans?
I’d like to see myself working on more advertisements and collaborating with designers / brands in the near future. As well as becoming bi-coastal between Los Angeles and New York. I love LA and this will always be my home but New York has different resources and is more in-tune with the fashion world, which will take my career to the next level.
Contact Info:
- Website: www.JessyCain.com www.WhatJessysWearing.com
- Email: [email protected]
- Instagram: @jessy_cain








