5 Black Icons Who Transformed Fashion—From Diana Ross to Rihanna

Diana Ross, with her big hair, big jewelry, big style and big attitude, has mattered since she first commanded attention in the 1960s as the most famous third of the Supremes. Ms. Ross (or “Miss Ross” in her Motown days) keeps the glamour quotient high to this day with accessories like huge sunglasses (often in bright shades like yellow), fur coats and serious gems. As her solo career thrived in the ’70s, the diva’s stage outfits hit their glittery groove. Over-the-top designer Bob Mackie created winking looks for her: A one-shouldered sequined gown printed with watermelons was not subtle. Even when Ms. Ross dialed it back, as she did in a white T-shirt on the cover of her 1980 album “Diana,” she had presence. Her glam trajectory arguably peaked at a 1983 outdoor concert in Central Park, where her many costume changes included a red, sequined catsuit that withstood a torrential downpour and no doubt empowered a generation of wannabe minxes. As the New York Post declared: “Diana Rains Supreme.”

2. KANYE WEST

THE SNEAKER AUTEUR

The rapper who slumped on the cover of his first album (2004’s “The College Dropout”) in a rather frumpy bear suit has become a fashion plate—Vanity Fair put him on its International Best-Dressed List—and a designer in his own right. His subdued Yeezy line with Adidas is a love letter to the insider sportswear designers he adores, including Helmut Lang and

Raf Simons.

The musician and his much-photographed family are walking advertisements for his own cozy, earth-toned loungewear and hyped sneakers. With so many admirers eager to emulate Mr. West’s luxurious sneakerhead aesthetic, the kicks he designs inspire multiday lines outside retailers and multi-thousand dollar prices on eBay. As Mr. West told Zane Lowe of the BBC, “No one can say I cannot design or understand how to design a guy’s sneaker.”

3. RIHANNA

THE STREETWEAR EMPRESS

The Barbados-born pop phenomenon Robyn Rihanna Fenty has built a fashion and beauty empire around her untimid sense of style. Ms. Fenty breaks ground most notably when she pairs streetwear-influenced looks with elevated constructions and designs. Case in point: the iconic—and completely sheer—Adam Selman gown she wore to the 2014 CFDA awards. The break-the-internet look combined high-fashion decadence (over-230,000 crystals, a strategically deployed fur stole) with a du-rag-inspired headdress that riffed on urban streetwear. That mix of aspirational and unexpected is what compels her acolytes to snap up the $50 lace version of her signature du-rag from her fashion collaboration with Puma.

4. PAM GRIER

THE BODACIOUS NATURAL BABE

One of the biggest stars of the blaxploitation film genre that helped define the ’70s, North Carolina-born actress Pam Grier exuded a new kind of on-screen appeal, one rooted in natural beauty and down-to-earth pieces like denim cutoffs, button-up shirts and hoop earrings. As the titular character in “Foxy Brown” and “Coffy,” Ms. Grier inspired a new generation of women to bare their midriffs and cultivate lush afros. Those halter tops might feel too brazen today, but Pam Grier’s sass and confidence are still just right.

5. SPIKE LEE

THE HIGH/LOW INDIVIDUALIST

If it’s game night at Madison Square Garden, you can bet that New York Knicks superfan Spike Lee will be sitting courtside in his signature basketball jersey and colorful spectacles. Since his appearance as Mars Blackmon in his own 1986 film “She’s Gotta Have It,” Mr. Lee has pioneered a high/low look featuring designer frames and New York- and Brooklyn-centric logo gear. Thirty-two years later, “She’s Gotta Have It” has been reprised as a new Netflix series and Lee’s brightly colored specs and athletic wear are an established part of the contemporary style lexicon.