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ZZ Top, Rancho Texicano: The Very Best of ZZ Top (2004)

With their dime-store sunglasses and signature chest-length beards, ZZ Top was not exactly known for being fashion forward. Still, the group’s gritty style fit perfectly with its bold, bluesy, and fantastically vulgar tunes. Check out a wealth of clothing-inspired tracks on this compilation, including “Blue Jean Blues,” “Cheap Sunglasses,” “A Fool For Your Stockings,” “Sharp Dressed Man,” and the crass yet sexy hit, “Velcro Fly.”

Run D.M.C., Raising Hell (1986)

Pioneering hip-hop trio Run D.M.C. wore Adidas brand sneakers religiously, and in 1986 they wrote a song about "My Adidas." (Adidas returned the favor in 2005 by designing a Run D.M.C. sneaker that was just like the original, but without the laces.) Raising Hell, Run D.M.C.’s breakthrough album features this gem as well as several other hip-hop classics, including “Peter Piper,” “It’s Tricky,” and the well-known collaboration with Aerosmith, “Walk This Way.”

David Bowie, Scary Monsters (and Super Creeps) (1980)

Bowie, a London-born rock phenomenon, made a name for himself by producing exciting, innovative, and sometimes strange music while regularly reinventing his personal style to deviate from mainstream trends. (You might even call him the rock “maverick” of his day.) His hit single “Fashion,” which appeared on his 1980 album Scary Monsters (and Super Creeps), has been interpreted as a subtle commentary on the ways in which the public can be bullied into conformity. Interestingly, a decade after the release of this somewhat cynical tribute to fashion, Bowie married world-renowned supermodel Iman.

Nancy Sinatra, Boots (1966)

Watch out for Ms. Sinatra’s white, patent leather, knee-high footwear! This singer’s 1960s hit single, “These Boots Are Made for Walkin,’” was the “Independent Woman” (you know, Destiny’s Child?) of its day. Recently re-recorded by Lil’ Kim, Jessica Simpson, Jewel, and Ginger Spice from the Spice Girls, the song remains a feisty anthem for the betrayed woman.

The Kinks, Kinks (2002)

Like David Bowie, the Kinks penned their 1966 single, “Dedicated Follower of Fashion,” to poke fun at those who insisted on following the latest trends: “They seek him here, they seek him there / His clothes are loud, but never square / It will make or break or break him, so he’s got to buy the best / ‘Cause he’s a dedicated follower of fashion.” It’s one of The Kinks’ most enjoyable hits, and a karaoke favorite.

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