Rihanna struts through John F. Kennedy Airport looking like a sneakerhead’s kid sister instead of a Grammy-winning recording artist. Rocking shades, a loose Chloë Sevigny for Opening Ceremony top, a Trapstar cap (turned backwards) and Playoff Air Jordan 12s, the Barbados-bred singer’s attire reads tarmac trendy. Though the ensemble may not be runway-worthy by Anna Wintour’s standards, the fashion blogs are going to grade her fashion street smarts as meticulously as Joan Rivers on Fashion Police within hours.
While dressing down may be on the come-up, ladies in street wear is nothing new. In the early 1990s, singers Aaliyah and TLC were glamorizing tomboy threads, rocking baggy jeans and over-sized shirts out of personal preference. Over a decade later, starlets like the “We Found Love” singer are swapping their tight-fitting wardrobe for boyish duds, tying high-end names with it.
“People have always believed that you had to have the highest heel and the shortest skirt to be attractive but [female celebrities] are letting you know that it’s okay to have a bit of a tomboy edge and flare,” says Claire Sulmers, Editor-in-Chief of fashion site Fashion Bomb Daily. “It’s about time women should be comfortable.”
Before the recession of 2008 hit, male celebrities seemed to be the pioneers of the high-end-low-end frontier. Sean “Diddy” Combs launched his contemporary Bad Boy clothing line in 1998 that initially tailored to the men but eventually expanded to the women. Jay-Z and Dame Dash then built Rocawear, which has grossed $700 million in annual sales since its inception in 1999. The owners doubled as brand ambassadors, appearing in public with logo-tatted jeans, white tees, leather jackets and Timberlands–the upscale version of urban.
Now the women are following suit.