It wasn't even a question whether or not you needed Timberlands in the '90s. For terrible weather, putting in work, or just looking rugged as hell, this was an OG workwear brand that was around for a minute before rappers and millions of fans made these boots a necessity. They appeared in dozens of videos, performances, and lyrics. When Biggie rhymed, "Timbs for my hooligans in Brooklyn," it was a wrap on deciding whether or not you wanted a pair.