Launched in 2021, the Keep Em Guessing OG Trucker Hat is where timeless street style meets bold originality. Featuring the original Keep Em Guessing logo, this hat is the statement piece that started it all. Built with a classic mesh back for breathability and a structured front panel, it delivers that effortless, lived-in vibe with every wear.
Whether you’re laying low or making moves, the OG Trucker Keeps Em Guessing while you stay one step ahead. Comfortable, versatile, and made to turn heads—this isn’t just a hat, it’s an attitude.
