Our History

Oakbay Fits was founded in 1994, when Isaac Charles, a LA native, left behind his record label job and decided to start a clothing company with longtime friend Deryk Hudson, a young graphic designer from the Bay area. Starting with $5,000, the two were able to create the timeless Oakbay logo and a small production of t-shirts, hats, and sweatshirts. In 1995, the brand quickly gained momentum throughout Los Angeles and the Bay area. With a huge grassroots following, Oakbay Fits was quickly embraced by the street fashion communities and some of the most prolific artists of our time. During 1995, Notorious B.I.G. graced the cover of Rap Sheet Magazine and also the pages of Vibe Magazine wearing several pieces from the Oakbay Fits Line. Other notable artists to rock the line include: Dr. Dre, Snoop Dogg, The Liks, Tyrese, Richie Rich and several other major artists within the music and entertainment industry. Oakbay has always represented a West Coast laid back lifestyle and attitude but with a global appeal.

Our Vision

In 2014, Isaac Charles relaunched Oakbay Fits on its 20 year anniversary. Designed with the best graphic designers and artists, twenty years later Oakbay Fits has picked up where it left off; with a strong focus on delivering authentic, quality goods. Oakbay Fits will always represent the culture of Hip Hop, streetwear fashion, underground artists, designers, trendsetters, any and all with aspirations of only wanting the best in life!