21 Pineapples is a fun, whimsical Hawaiian-inspired apparel brand spearheaded by a man on a mission, Nate Simon. His message to the world is to always be a good human, spread love and cheer, and don’t be a bully or hurt others. The clothing is pretty darn cool, too.



Be a good human and spread the love. That’s the mantra behind 21 Pineapples, which is all about spreading awareness about Down syndrome and fighting off bullies. You know, the not so nice, judgmental people that often don’t have anything positive to say. It’s a solid mission and a message I can get behind, and I hope many of you, as well. As for why I’m bringing it up, 21 Pineapples is a unique, Hawaiian-inspired clothing brand with polos, tees, crewnecks, hoodies, and a variety of apparel, available in many sizes and for all ages.

A whimsical and fun spirit carries through all the designs, from the “Do Cool Shit” tee to the Be a Buddy Not a Bully long-sleeve. Of course, the signature designs, and some of Nate’s favorites, are the Hawaiian polos. The 21 Pineapples “Rockin’ Pineapples” Polo or the “Drink Up” Polo are excellent examples. It’s the perfect time to discuss it all, too, because October is Down Syndrome Awareness Month. It’s a time to come together and celebrate the abilities and attributes of anyone born with the condition. As Nate and company say, “Some see a disability, but we see endless abilities.”

Who is Nate Simon the CEO of 21 Pineapples?

Started by Nate and his mother, 21 Pineapples is on a mission to change the way others perceive those with Down syndrome, and similar special abilities, through modern apparel. “One Hawaiian shirt at a time,” they proudly proclaim. Approximately one in every 775 babies in the United States is born with Down syndrome, which is about 5,000 babies each year. It occurs in people of all races and economic levels, and those with the condition attend school, go to work, actively participate in decisions that affect their lives, and also have meaningful relationships and contribute to society in many wonderful ways, like offering some amazing shirts and apparel.

While those with the condition do experience cognitive delays, the effect is usually mild to moderate and does not alter their strengths, talents, and abilities. That’s precisely the message that Nate and his family want to put out into the world. Something like this doesn’t define who you are and doesn’t limit your potential to do great things. If you want to get behind this message, or check out some kickass clothing, head on over to 21 Pineapples.

Who is it for?

Anyone who likes to wear cool clothes with great designs that support an inspirational cause. 21 Pineapples is the place to shop for good, caring humans.

Where to buy?

MSRP: From $30