Wilhelmina New York’s Bobby Gutierrez Reveals What It Takes to Make It in Fashion

This month, we caught up with a local boy who’s risen through Wilhelmina’s ranks.
photo: david croxford, location: manifest, 32 n. hotel st. 


Last month, we interviewed Roman Young, the director of Wilhelmina International’s Women and Image Division, about the ins and outs of the fashion industry. This month, we talk to another local boy who’s risen through Wilhelmina’s ranks: Bobby Gutierrez, image and celebrity manager for Wilhelmina New York. He’s responsible for handling the fashion aspect of his clients’ careers, mostly musical artists and models, and booking them for designer campaigns, editorial covers and features for publications such as Vogue, Elle, Allure and Harper’s Bazaar. It’s what he calls, “taking care of his girls.”


Tatted arms, leather Army boots, dressed in all black—at first glance, Gutierrez reads intimidating. Then the Honolulu-born agent cracks a smile, and you begin to feel comfortable. Chat with him for five minutes and you realize he’s thoughtful, fun and reliable, which is why he’s so damn good at his job. 


A born hustler, “Jobby Bobby,” as he’s been crowned by his close friends, has always been a hard worker, from his days of rolling out dough at the Pearlridge Cinnabon and dressing up like the Easter Bunny to doing makeup for Courtney Love and, now, representing superstar celebrities, such as Iggy Azalea. Here, Gutierrez opens up about life in New York, what it takes to make it, and how he snagged a rare photo with the most influential person in fashion. 


HONOLULU Magazine: What’s a normal day for you?

Bobby Gutierrez: I get up about 6 a.m. At 7 a.m. I head to the gym (sometimes!) and then rush off to work. I grab my coffee and by 10:30 I’m checking in with my girls and seeing if everyone is doing okay. My daily list includes emailing clients, scheduling shoots, calling new clients, booking editorials and usually ends with an after-work event. 


HM Growing up in Hawai‘i, what would have been a normal day?

BG: If I can only remember! Let’s see, waking up to the smell of my mom cooking Portuguese sausage, eggs and kālua pig. On a normal weekday, I would go to school, then hang out with my friends after school either at Sandy Beach or Pearlridge. I would take the number 32 bus there, back when it was only 25 cents!  But in the back of my mind, I was always thinking about what I was going to do with my life.


HM: You left the Islands in 1998 to pursue a career as a makeup artist in Los Angeles. Was it hard to leave? And what was the journey like?

BG: Yes, because I love Hawai‘i and I hated leaving my friends behind. But, I knew that I wanted to venture out and discover a new surrounding. 

Over the years, my career as a makeup artist flourished and my clientele included some of the world’s most desirable women—Sofia Vergara, Eva Mendez and Vivica A. Fox. During that time I also worked in the Wilhelmina Los Angeles office helping out with open-call castings and going to New York to help out during Fashion Week. I was with Keke Lindgard (local girl turned top model) during her very first season. It was so exciting. She was confirmed for more than 18 of the industry’s top shows. 

After a few trips to N.Y., in 2011, I decided to make the move (by flipping a coin). Since then, my adventures in the Big Apple have been nothing short of amazing.


HM: What are some highlights of your current position?

BG: I’ve been with Wilhelmina for almost five years and I love my job. It allows me to travel all over the world, attend major social events and meet famous designers, photographers and those who have a strong presence and influence within the world of fashion. 


HM: What advice would you give to young local talents preparing to leave home to chase their dreams? 

BG: The biggest adventure you can take is to live the life of your dreams, because if you don’t take that chance, someone else will pursue it. Remember, if things don’t work out you can always change, whether it’s a job, relationship or where you live. Everything is fixable! 

And, make friends with someone that works for Hawaiian Airlines. A buddy pass is a golden ticket to come home!


HM: You got to be a part of the first-ever HONOLULU Fashion Week. What were your end thoughts? 

BG: I was so proud and impressed with the amount of local talent we have. From designers, photographers to makeup artists, hair stylists and musicians, it was exciting to see everyone come together to produce some amazing shows. I can’t wait for the next one!


HM: Speaking of fashion shows, New York Fashion Week is this month. What’s one thing you always bring with you?   

BG: My iPhone to capture backstage moments, and a stylish new hat. 


HM: Any recent snapshots worth mentioning? 

BG: I took a selfie with Anna Wintour. I was backstage at a Rag & Bone show and Anna walked in, and of course, the room became silent. Anna has that power—she can make or break you as a designer. I went up to her and politely asked if I could take a photo with her. She said, “of course.” I asked this young hipster boy standing next to me to take the picture and he was so nervous that he couldn’t stop shaking while taking the photo. But, after two takes, we finally got it. Anna was very nice and I even got a hug after!


HM: Final words?

BG: Work hard. Stay humble. 


Read More Stories by Stacey Makiya