Skip to content
  • Essence GU
  • Beautycon
  • NaturallyCurly
  • Afropunk
  • Essence Studios
  • Soko Mrkt
  • Ese Funds
  • Refinery29
  • WeLoveUs.shop
  • 2026 ESSENCE Festival Of Culture
  • Celebrity
  • Fashion
  • Beauty
  • Lifestyle
  • Entrepreneurship
  • News
  • Shopping
  • Video
  • Events
  • Subscribe
Home • Celebrity

Rihanna's Best Fashion Moments

Fifty reasons why she won the CFDA Fashion Icon of the Year award.
By Celia L. Smith · Updated October 27, 2020
Getting your Trinity Audio player ready…
01
Red Carpet Style

Rihanna’s fearless fashion sense and the attitude in which she carries her style is exactly why she was recognized by the Council of Fashion Designers as the Fashion Icon of The Year. At the award ceremony the singer’s Adam Selman designed, Swarovski crystal embellished, see-through gown and matching head scarf stole the show, channeling the late great Josephine Baker.

Rihanna's Best Fashion Moments
Larry Bussaca/Getty Images
02
Red Carpet Style

Rihanna was so in love with last year’s punk theme, she re-lived it again this year. The singer donned a white bold shoulder cropped top and ruched floor-length skirt by Stella McCartney.

Rihanna's Best Fashion Moments
Getty Images
03
Red Carpet

While Rihanna’s doobie wrap was the center of attention at the American Music Awards it was her Jean Paul Gaultier bead and lace brasierre style gown that caught our attention.

Rihanna's Best Fashion Moments
Dominique Charriau/WireImage
04
Stage Style

When it came time to accept the Icon Award onstage at the AMA’s, Ri-Ri opted for yet another sexy JPG gown.

Rihanna's Best Fashion Moments
Lester Cohen/WireImage
05
Red Carpet Ready

The singer softened up her style in a sheer Azzedine Alaia gown at the GRAMMY Awards that appeared as if she rose from the red carpet.

Rihanna's Best Fashion Moments
Larry Busacca/WireImage and Jason Merritt/Getty Images
06
Stage Style

There was no other way for the singer to kick off her Diamonds world tour, than by shining bright in this custom Lanvin jumpsuit.

Rihanna's Best Fashion Moments
S Fernandez / Splash News
07
Stage Style

Rihanna gets raunchy in embroidered hot pants and matching coat, a leather bra top to rival Madonna’s and thigh-scraping lace-up boots, all by Givenchy.

Rihanna's Best Fashion Moments
George Pimentel/WireImage
08
Stage Style

Before Olivia Pope made white coats popular, Rihanna worked the crowd in Morocco sporting an oversized Miu Miu style, with Lanvin accessories and Gianvitto Rossi knee-high boots.

Rihanna's Best Fashion Moments
Joelle Vassort/Maxppp /Landov
09
Stage Style

In Singapore Ri-Ri brightens things up, ironically in a Raf Simons look from his Spring ’13 men’s runway. If anyone could pull it off, she can.

Rihanna's Best Fashion Moments
Chris McGrath/Getty Images
10
Stage Style

In Middle East garb with an urban twist, Rihanna performs on stage at Abu Dhabi wearing white layers of the Kokon To Zai menswear collection.

Rihanna's Best Fashion Moments
KARIM SAHIB/AFP/Getty Images
11
Street Style

Heading out with friends for the night in London, Ri-Ri doesn’t rock just any typical baseball style bomber, hers is a seriously hot Roberto Cavalli style.

Rihanna's Best Fashion Moments
Rex USA
12
Street Style

The singer takes her most talked about hair style off the red carpet and onto the streets with a Torn By Ronny Kobo dress and Giuseppe Zanotti thigh-high boots.

Rihanna's Best Fashion Moments
247PapsTV / Splash News
13
Street Style

Rihanna was court-side chic on Christmas day in a black cropped top and black skinnies, accented by a gold Christian Lacroix choker, body chain and Manolo Blahnik heels.

Rihanna's Best Fashion Moments
Noel Vasquez/Getty Images
14
Street Style

Layered in her own line (Rihanna for River Island) and Versace glasses, the singer hits the Miami streets.

Rihanna's Best Fashion Moments
Jonathan Pavel/FilmMagic
15
Street Style

The singer can’t be missed in a cherry red Zac Posen style with goth style creepers and a choker.

Rihanna's Best Fashion Moments
Luca Chelsea / Splash News
16
Street Style

In full-on 90s-inspired regalia, Ri-Ri walks the street risqué in a crush velvet Rihanna for River Island “playsuit” and thigh-high suede boots.

Rihanna's Best Fashion Moments
247PapsTV / Splash News
17
Street Style

On a night out dining at Nobu, the singer was spotted wearing the jumpsuit of all jumpsuits: Balmain’s leather with gold hardware style with matching metal-tipped boots, straight off the runway.

Rihanna's Best Fashion Moments
Michael Stewart/WireImage
18
Street Style

Cropping it like it’s hot, the diva dons a Versace look from the resort ’14 runway collection with matching Manolo Blahnik’s for the opening of the new M.A.C cosmetics store in Hong Kong, China.

Rihanna's Best Fashion Moments
TPG/Getty Images
19
Street Style

The singer serves style with severity in a River Island bodycon she designed that’s sure to make anyone run to buy it.

Rihanna's Best Fashion Moments
Splash News
20
Street Style

Rihanna’s a global girl and she’s wearing it loud and proud in a flag printed Kokon To Zai oversized T-shirt and drop crotch trousers, a Vivienne Westwood clutch and lugged sole boots while hitting the streets of London.

Rihanna's Best Fashion Moments
Neil P. Mockford/FilmMagic
21
Street Style

After the show it’s the after party, and Rihanna was spotted leaving one the morning after the VMA’s in a bodycon Balmain and her signature Manolo Blahnik sandals with cocktail in hand.

Rihanna's Best Fashion Moments
Splash News
22
Street Style

We love that Rihanna rocks pieces straight off of the men’s runway. In London, the singer channels her inner David Bowie with this checkered Saint Laurent moto jacket and mullet cut complete with Manolo’s for a ladylike finish.

Rihanna's Best Fashion Moments
Neil P. Mockford/FilmMagic
23
Street Style

In full-on 90’s nostalgia style, Rihanna sits front row at the Opening Ceremony show in a silver paisley print Zac Posen dress with Agent Provocateur tights and creeper shoes by Underground.

Rihanna's Best Fashion Moments
Taylor Hill/FilmMagic and Brian Killian/WireImage
24
Street Style

Repping her River Island collection again, the singer is feeling fashion fatigue while casually dining at Da Silvano’s.

Rihanna's Best Fashion Moments
Splash News
25
Street Style

Mary Kantrantzou’s playful butterfly tunic and Tom Ford gladiator sandals make one killer combo for a night on the town.



Rihanna's Best Fashion Moments
Alo Ceballos/FilmMagic and NCP/Star Max/FilmMagic
26
Street Style

Rihanna takes to the streets in whatever she pleases, this time it’s a Roman-inspired look disguised in a another backwards cap, Chanel shades and necklace and Rihanna for River Island cut-out boots.

Rihanna's Best Fashion Moments
Jackson Lee/Splash News
27
Street Style

At the launch of Rihanna’s clothing and shoe collection for River Island in London, the singer opted to wear the sexiest piece of all –– a high split bodycon with her favorite Manolo heels.

Rihanna's Best Fashion Moments
Getty Images
28
Street Style

On a girlier note, Rihanna rocks a full Balmain look in a robin’s egg blue shade fit for Easter day.

Rihanna's Best Fashion Moments
Splash News
29
Street Style

Even filming a Budweiser commercial is a fashionable fete for Ri-Ri. The singer donned a cropped jacket, knit pencil skrt and Azzedine Alaia shoes for a look that was utterly chic.

Rihanna's Best Fashion Moments
Aby Baker/Getty Images
30
Street Style

In head-to-toe Chanel, the singer looks like the chicest school girl there ever was while patrolling the streets of Paris.

Rihanna's Best Fashion Moments
Marc Piasecki/FilmMagic
31
Street Style

The singer’s too-cool-for-school overalls and pumps is a definite Sex And The City style moment.

Rihanna's Best Fashion Moments
Beretta/Sims/Rex/Rex USA
32
Street Style

Only Ri-Ri could make one of the simplest ensembles look cool, like this leather T-shirt paired with ridiculously fly Tom Ford boots.

Rihanna's Best Fashion Moments
Splash News
33
Street Style

This “Ri-Ri Woo” red, high-gloss Miu Miu skirt was a traffic stopper in Manchester.

Rihanna's Best Fashion Moments
Beretta/Sims/Rex/Rex USA
34
Street Style

Dark and moody was the vibe behind this Kokon To Zai menswear-inspired look and Silver Spoon beenie –– an ode to London grunge.

Rihanna's Best Fashion Moments
Neil P. Mockford/FilmMagic
35
Street Style

The singer pays homage to real street style with a few classics: an oversized Adidas sweatshirt, bandana and Ray Ban Wayfarers.

Rihanna's Best Fashion Moments
Splash News/All Over Press
36
Street Style

Rihanna photo bombs photographers in a bright blue lipstick and a bomber jacket we’d rock from Rihanna for River Island SS14 collection.

Rihanna's Best Fashion Moments
Rex USA
37
Street Style

This clean summer-white ensemble and saddle-colored visor worked perfectly across the pond for Rihanna.

Rihanna's Best Fashion Moments
Neil P. Mockford/FilmMagic
38
Street Style

Rihanna clearly isn’t afraid of being completely transparent with her fans and this Adam Selman mesh short set proves it. Balenciaga sneakers and Prada sunglasses takes the singer’s summer white style to new heights.

Rihanna's Best Fashion Moments
REX USA
39
Red Carpet Style

Riri arrived on the red carpet of her flick Battlefield in Sydney, Australia wearing a clean lined Stella McCartney jumpsuit, gold hoops and Manolo Blahnik sandals.

Rihanna's Best Fashion Moments
40
Street Style

In true London fashion, Rihanna sports a psychedelic tuxedo blazer by Brit designer Stella McCartney. She paired this look with Barton Perreira Kevin sunglasses and her favorite ankle strap sandals by Manolo Blahnik.

Rihanna's Best Fashion Moments
41
Stage Style

At the 2012 Victoria’s Secret Fashion Show the singer naturally chose a sexy lingerie look for the stage in a girly pink see-through nighty with a white panty and bra set.

Rihanna's Best Fashion Moments
Getty Images
42
Red Carpet Style

Sexy, stunning, and bold was Rihanna’s Armani gown at the 54th Annual GRAMMY Awards in 2012. Hands down, best dressed and most buzzed about look of the night.

Rihanna's Best Fashion Moments
43
Stage Style

We went gaga for Rihanna’s burlesque stage style at The 2012 Victoria’s Secret Fashion Show in New York City. It was over-the-top but that was everything we loved about it.

Rihanna's Best Fashion Moments
Getty Images
44
Street Style

Clad in Karl Lagerfeld’s designs, Rihanna attends the Chanel show as part of Paris Fashion Week Haute Couture Fall/Winter 2013-2014 at Grand Palais in Paris, France.

Rihanna's Best Fashion Moments
Dominique Charriau/WireImage
45
Red Carpet Style

At the 2012 BRIT Awards the singer sparkled in a Givenchy crystal gown and leather opera gloves in London.

Rihanna's Best Fashion Moments
DAVE M. BENETT/GETTY
46
Red Carpet Style

Rihanna owns her edgy bad girl style and works it. We can always count on her to kill the red carpet in something sexy — like this exotic Tom Ford croc style or a see-through, backless and plunging number.

Rihanna's Best Fashion Moments
Larry Busacca/Getty Images
47
Red Carpet Style

Things get prim and proper for Rih-Rih at a Chanel fashion show in Paris. A lovely shade of lavender from cropped top to kicks, complete with pearls on her wrist courtesy of Chanel.

Rihanna's Best Fashion Moments
FRANCOIS GUILLOT/AFP/Getty Images
48
Street Style

Rihanna decked in Dior; a bold red fur, satin dress, and thigh-highs with all of the right accessories at the Christian Dior show in Paris.

Rihanna's Best Fashion Moments
PATRICK KOVARIK/AFP/Getty Images
49
Street Style

At eco designer Stella McCartney’s fashion show this season, the singer sits appropriately in an envious shade of green from Stella’s collection with cat-eye sunnies to complete her catty look.

Rihanna's Best Fashion Moments
Dominique Charriau/WireImage
50
Street Style

The singer poses in a menswear-inspired Lanvin look we love, with none other then the Lanvin designer himself, Alber Elbaz

Rihanna's Best Fashion Moments
Rindoff Petroff/Dufour/Getty Images
TOPICS:  Rihanna