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Double or Nothing

Drew Bailey and Mike Forrester are the minds behind the Greater Hartford based clothing brand Double or Nothing Apparel.

Written & Photographed by
Jasmine Jones

Drew Bailey, Jaiden Bailey, & Mike Forrester

The duo behind the Greater Hartford based clothing brand Double Or Nothing Apparel consists of Drew Bailey and Mike Forrester—cousins, Hartford natives, and music lovers who live by the motto that now covers their apparel, “Double Or Nothing, Built to Win.” Despite launching just this past June, they have been expanding rapidly, with sales reaching Toronto, California, Florida, and more. We met up with the pair to get more insight into who they are, what their label stands for, and what they have planned for the future.

What is Double Or Nothing Apparel?

Double Or Nothing Apparel (D.O.N) is a clothing brand featuring stylish yet comfortable all-purpose attire. It embodies the idea of going all-in, according to co-founder Drew Bailey, who explains it as going “all-in on yourself, betting on yourself, and investing in yourself. We believe you are your best investment.” Co-founder Mike Forrester shares this belief, stating that, “You have to invest in yourself in order to get equity in the long run.”

Who are the minds behind the brand?

Drew Bailey and Mike Forrester, both born and raised in Hartford, Connecticut have always had motivational mindsets. Forrester credits his strong family structure as inspiration and motivation towards his entrepreneurship goals. He explains how Double Or Nothing Apparel aims to “elevate our people in effort to uplift the world.” He believes that the brand is a way for their voices to be heard. Bailey sees D.O.N Apparel as a way to “give back to the community and leave something behind that’s positive for our families.”

What is the inspiration behind the name?

The name comes out of the conviction that one should bet on themselves and believe in their vision. “When you have a strong passion for something you truly believe in, it will drive your work ethic towards setting and accomplishing new goals,” Bailey begins to explain, and being passionate and consistent is a big contribution to the brand’s success so far. “We believe in this brand. We’ve always loved fashion, music, arts and the culture, so we went all-in, Double Or Nothing. We took a leap of faith because we’re passionate about our brand.” Forrester describes the name as “a feeling and a mindset turned into a lifestyle that we use for motivation.” He credits his upbringing and life benchmarks as an inspiration for the brand’s name as well. “Double Or Nothing Apparel’s brand symbolizes unity and equality. Our apparel is a way for our voice to be heard, as we fight towards justice for all Black and Brown people.”

What is the inspiration behind the style?

“Our family is from Jamaica, where color is better. Living in color symbolizes positive energy,” Forrester states. “We use color to express our culture.” Bailey elaborates, saying that they “come up with different color patterns that we think people would like. Someone might say, ‘Oh, that’s my fraternity color, that’s my sorority color, that’s my favorite sports team’s color.’ We want to be able to connect with and inspire as many people as possible.” They credit music as an influence on their brand’s style as well. “Music is life, music is motivation, music is inspiration,” Forrester explains. “It gets you through things, I listen to music every day, and I learn a lot from music. I try to apply it to my everyday life.” And what kind of music are they inspired by? Hip Hop, R&B, Reggae, Gospel, and Jazz to name a few. Bailey says that they take a little something from each genre, allowing them to all “correlate into one.”

What type of clothing do you provide?

Forrester lists having all-purpose unisex attire as a key component to the brand. “We want you to feel comfortable and stylish at the same time. We want you to be able to wear our attire to the gym, the grocery store, to go out and have fun, to play sports, any purpose possible. We want it to be everyday wear.” Although they started with dad hats, the brand quickly began selling shirts, hoodies, and soccer jerseys, with sweatsuits and gym attire coming soon. They plan to continue branching out, touching all levels of apparel, from backpacks to coats to varsity jackets. Everything that the pair creates comes in unisex, as their aim is to cater to a wide audience. “Men, women, seniors and young folks,” Bailey elaborates, “We want to have an item for everyone.”

Where can we find Double Or Nothing Apparel?

Instagram: @doubelornothingapparel



See more photos in the printed issue - Issue 008, Fall 2020! Available in the Aislin Shop.