Meet James Simpson


You've probably noticed his cool and confident look in our marketing, but did you know James Simpson is also a multitalented individual with a passion for sustainable living? From bartending in vibrant locales to dabbling in DJing, James has a diverse background that's as dynamic as his style.

What struck us most when we met James is his genuine commitment to sustainability and his ability to make our eco-friendly fashions his own. His mindful consumerism and dedication to wellness perfectly align with our brand's ethos.

Today, we're excited to pull back the curtain and introduce you to the man behind the style, sharing his unique bond with The Green Pineapple and what makes him a true ambassador of our brand.

Q&A with James Simpson

James Key West Model

How did you end up in Key West?

Before moving to Key West, I was spending the summers in Provincetown, MA, and the winters in South Beach, FL. The season had ended in Provincetown, and I was contemplating where to go next for the winter when a friend from P-Town called me and put the idea of Key West in my head. The rest is history.

What do you enjoy most about living here?

I’d have to say I love how quiet and peaceful Key West is. It’s a safe, quirky town, and I enjoy the people within the community that I’ve had the pleasure of getting to know personally. I’ve been here for three years, and I feel like I still find new things I’ve never seen before, like all the different plants and flowers that flourish all around the island.

Where is your favorite place to take out-of-town visitors?

I feel like no trip to Key West is complete without heading to The Hemingway House, Butterfly Museum, Fort Zachary Beach to check out the old fort, go snorkeling, and watch the sunset. La Te Da is also a must for dinner, live music, and the cabaret show.

Is modeling your primary occupation?

That sounds like a ton of fun, but I wish! At the moment, it is just a fun hobby. I never went to college, but I’ve worked a variety of different jobs from retail, a teller in a bank, identity theft at the IRS, working in a chemo treatment center in a hospital, and most recently, a student coordinator at a college… the irony of that without a college degree. I guess we can say I’ve come a long way from gathering the carts together in the parking lot at Stop and Shop at 15 years old. For now, my main job is bartending, which has allowed me to make a living as well as work in many cool places like Provincetown, MA, Fire Island, NY, South Beach, FL, and now Key West.

James Simpson, Key West Model

What are your hobbies in Key West?

I just started tapping into DJing. It’s something I’ve been wanting to do for quite a while, so I’m excited to put my ideas together to see where it takes me. I’m not taking it too seriously, just having fun.

How would you describe your style?

I can’t think of a particular style that would define me. I need to be comfortable in whatever I’m wearing. I really like finding different clothing items at boutiques and online, then putting an entire outfit together from top to bottom with accessories.

What is your favorite fashion piece/accessory?

I can’t leave the house without a pair of sunglasses.

As you know, at The Green Pineapple, we emphasize sustainability and quality clothing. What are the top 5 Green Pineapple items you'd include in your capsule wardrobe?

My top 5 would be The Green Pineapple Esteban T-Shirt, The Green Pineapple Miles Cashmere Polo, The Green Pineapple Ricardo Button Down Polo, Joulter Linen Shorts, and Randall Linen Trousers in white.

Were you familiar with or had you visited our boutiques or Wellness Cafe before modeling for us?

I started coming to Green Pineapple because of the Wellness Cafe for smoothies, and over time, I got better acquainted with the staff, who eventually became friends. I’ve also enjoyed the private farm-to-table dinners hosted there.

What's your favorite item from the Green Pineapple Collection, and could you describe how its fabrics feel for our online shoppers?

The Miles Cashmere Polo has to be my favorite item. It’s one of the most comfortable, soft pieces of clothing I’ve ever worn.

What was the last item (or your favorite item) you ordered from our Wellness Cafe?

I always get the same Blue Magic Smoothie that I modify, and of course, I can’t forget those famous chocolate chip cookies.

Do you practice conscious consumerism? If so, how?

Moving to Key West has changed my mentality as a whole, but certainly on my approach to buying and using products. Over the last couple of years, I’ve definitely become more mindful of the products I put in and on my body, even down to the products I use to clean my home. Sustainability and reusable products are key in my book.

Wellness is central to our mission. How do you maintain a healthy mind and body?

For me, the most important thing is setting healthy boundaries with your workplace, friends, and family. I have a small core circle of friends, which is extremely important to me. I make time for others, but I always put my mental and physical health as a priority. I watch what I consume and drink lots of coconut water.

Could you share your experience working with Rikki as a modeling partner?

She’s a natural and makes posing look so effortless. I was nervous, but Rikki calmed my nerves by being so kind and sweet. I’m looking forward to having a couple more shoots under my belt so we can create some magic in the future together for Green Pineapple.

James & Rikki Key West Models at The Green Pineapple Wellness Cafe

Embodied in his experiences and aspirations, James epitomizes the values of The Green Pineapple - community, sustainability, and wellness. To us, he's not just a face; he's a part of our family and an inspiration.

Are you interested in being a model or working with us at our Key West boutiques or Wellness Cafe? Contact us today and let's chat!