21 Pineapples: Spreading Love Through Fashion

When Holly Simon founded 21 Pineapples three years ago, she had a simple but powerful mission: to change how people view individuals with disabilities. Named after her son Nate’s favorite fruit, the business has become a beacon of inclusion, love, and positivity.

 

A Family-Inspired Mission

21 Pineapples isn’t just a brand; it’s a heartfelt tribute to Nate, Holly’s youngest son, who has Down syndrome. Nate is not only the inspiration behind the company but also a role model—he’s a successful model, actor, and social media influencer with nearly 1 million followers on TikTok. His joyful energy and natural charisma have made him a beloved figure, inspiring countless fans and customers to embrace the message of love and acceptance.

The brand’s mission is clear: to foster employment, opportunity, and love for people with disabilities. Every shirt created by 21 Pineapples carries this message, aiming to shift perceptions and inspire acceptance. Holly contributes ideas for the designs, which are brought to life by a team of talented artists.

 

Growing a Business with Heart

Operating from Chicago, 21 Pineapples serves customers across the United States and even internationally, with orders coming in from as far as Australia. In its first year, the company generated an impressive $2 million in sales—a testament to the brand’s growing appeal and message. Holly oversees operations with dedication, ensuring every product represents the love and care behind the brand.

The company specializes in vibrant, custom shirts, with Hawaiian-inspired designs consistently in stock. 21 Pineapples also donates to support futures for children with disabilities, reflecting their commitment to giving back to the community.

 

Nate: The Face of 21 Pineapples

Nate’s dynamic social media presence is a key part of 21 Pineapples’ marketing strategy. As a model, actor, and influencer, Nate’s achievements serve as proof that barriers can be broken with inclusion and understanding. His TikTok account, where he shares his infectious joy and advocacy for people with disabilities, has nearly one million followers. Beyond his social media fame, Nate has also succeeded in the entertainment industry, where he continues to shine as a symbol of possibility and perseverance.

 

Behind the Scenes with Holly Simon

Holly’s journey with 21 Pineapples is also a personal one. As a mother of five, she balances her roles as a business owner, published author, blogger, and advocate for inclusion. Beyond running her business, Holly enjoys painting and fashion, adding her personal touch to the company’s creative process.

Her passion for making a difference shines in every aspect of the business, from product ideas to philanthropy. Holly ensures that 21 Pineapples is more than just a shirt company—it’s a movement for kindness, inclusion, and understanding.

 

Looking Ahead

As Holly and her team gear up for the future, they are exploring long-term marketing solutions to maintain the brand’s momentum. With a follow-up scheduled to discuss upcoming strategies, the focus remains on sustaining the positive impact 21 Pineapples has made.

Holly’s dedication, coupled with Nate’s infectious energy and unwavering positivity, ensures that 21 Pineapples will continue spreading its message of love and acceptance far and wide. To learn more about Holly and Nate you can visit their website here.