Hufnagel was born in Manhattan, where he grew up in Stuyvesant Town–Peter Cooper Village;[1][2] his father was a vice president of Metropolitan Life Insurance and his mother a nurse.

[5] After living for a couple of years in Los Angeles,[8] he opened the first HUF Worldwide store in the Tenderloin neighborhood of San Francisco in 2002 with his then wife, Anne Freeman,[3][6] at her suggestion using the nickname he had already used on his skateboard decks and T-shirts.

[2] A pioneer of streetwear,[8] it carried rare sneakers and clothing by Supreme and other boutique fashion houses, and also art by other skateboarders and artists such as Aaron Rose and Haroshi.

[5][9] The boutique expanded into a chain based in Los Angeles and with stores in Texas, New York, and several in Japan,[8] and by 2007 to a lifestyle brand, selling activewear labeled with an "H" plus in some cases an irreverent collection motto such as "Dirtbag Crew" or "Fuck It".

[1][5] A sculpture by Haroshi of a raised middle finger, in the company's Los Angeles store, was destroyed in the protests following George Floyd's murder by police; Hufnagel responded by producing a T-shirt to benefit the Black Lives Matter movement.