29 Rihanna Outfits That Show Off Her Style Transformation, From Metallic Vests To All Those Awesome Pajama Moments

TOKYO, JAPAN - APRIL 03: Actress/singer Rihanna attends the 'Battleship' Japan Premiere at International Yoyogi first gymnasium on April 3, 2012 in Tokyo, Japan. (Photo by Koki Nagahama/Getty Images)
Source: Koki Nagahama/Getty Images Entertainment/Getty Images

Though her music may ignite some controversy and her personal life seems somewhat of a roller coaster, Rihanna's fashion has remained solidly, idiosyncratically sultry over the years. Even if Rihanna is wearing her pajamas, which she frankly does quite a lot, the singer manages to evoke an air of unadulterated charisma with each look, on the red carpet and off. And as of this year, Rihanna has been a media and fan fixation for a full decade. In honor of RiRi's incomparable decade of sartorial experimentation, here are the singer's best looks. Reader beware: some of these ensembles should actually be Rated R. 

In Metallic Vest At A Tempo Event in 2005

Clad in a metallic vest, cropped, faded jeans, chandelier earrings, and silver bangles, Rihanna hit all the style marks of a pop star-in-the-making. 

Gold Bikini-Clad In 2005

Princess Leia wants her bikini back, and for that matter, so does Beyonce’s character Foxxy Cleopatra from Austin Powers in Goldmember

In Bustier And Mom Jeans At MTV

I wish there was some redeeming quality in this ensemble, but the cringe-worthy high-waisted jeans and bustier pairing is beyond salvaging. Maybe this is why the singer started wearing her pajamas in public. On the bright side, RiRi is owning the neon nail polish.

In An Unexpected Hello Kitty Cardigan in 2006

Yes, Rihanna has a softer side. While visiting with children  at an event in 2006, the singer chose a pastel pink cardigan, rosy cosmetics, and jeans. The outfit has since disappeared from her wardrobe.

In A White Mini At The 2006 Billboard Music Awards

Though Rihanna’s vocals snagged four Billboard Music awards at the 2006 ceremony, it was her plunging white Marilyn Monroe-inspired mini that stole the show.

In Star-Spangled Dress At MTV in 2006

Remember when Rihanna wore real clothing on the red carpet? I didn’t either, which is why this gorgeous black and white number is such a refreshing stroll down memory lane.

At The 2007 American Music Awards

When Armani and Rihanna collaborate on an ensemble, beautiful things can happen. This quirky look, however, didn’t quite make the cut. 

In Zac Posen At The 2008 American Music Awards

The star surprised her audience with a frothy, feminine Zac Posen number at the 2008 American Music Awards

Stunning In Silver

After chopping her locks, the star revamped her look for the 2008 Brit Awards in a fitted Giambattista Valli mini. Bellissima, indeed.

In Leather During A 2008 Performance With Chris Brown

A leather mini and Chris Brown by her side? This look is classic retro Rihanna.

At The 2009 American Music Awards

Love it or hate it, this statement black and white Marchesa gown with floral cutouts avoids the staid sequined mini red carpet trope.

At The Chanel Spring 2010 Show In Paris

Rihanna brought on the bling to accent her timeless Chanel ensemble for the brand’s Spring 2010 runway show in Paris. C’est tres belle!

In Concert Wearing Fishnets, Bodysuit, And Boots

Is there a more classic Rihanna ensemble than thigh-highs and a bodysuit? 

In Marchesa At The 2010 MTV EMA's

Rihanna demonstrated her adoration of feather-light Marchesa again at the 2010 MTV EMA’s. Whatever she may sing about, Rihanna has a secret infatuation with ultra-feminine fashion.

Triple Red At The 2010 American Music Awards

A red haired and red lace-clad Rihanna ruled the red carpet at the 2010 American Music Awards. 

Bikini-Clad In Concert

2011 may have been the sartorial tipping point for Rihanna, because she seems to have worn less and less clothing ever since. As bikinis go, however, this neon-bright set is utterly fabulous. 

In Denim And Leather At A 2011 Concert

Britney Spears may have started a worldwide trend when she knotted up her shirt in that iconic scene of the Hit Me Baby One More Time video, but Rihanna took the look to an entirely new stratosphere by adding black patent hot pants and fishnets. 

Suited Up At The 2011 Billboard Music Awards

A white tuxedo never goes out of style, as Rihanna proved in this chic look at the 2011 Billboard Music Awards.

In White Lace At A Fragrance Event For Nude By Rihanna in 2012

Rihanna stepped out to promote her fragrance in this stunning white lace and bustier number, prompting paparazzi and fans to forget what the event was for in the first place.

At A Best Buy-Sponsored Promotional Event For Her Music in 2012

As intriguing as this slouchy leather-on-leather ensemble is, I’m delighted that Ms. RiRi has moved on from the look. With this much baggy clothing on, one might not even recognize the pop icon.

In Giorgio Armani At London Fashion Week, 2012

This gorgeous, slinky silk Giorgio Armani creation is simple, chic, and jewel-toned: the holy trinity of style.

At The Battleship Premiere In Tokyo

This Emilio Pucci ensemble worn to the premiere of Rihanna’s film Battleship so closely resembles a luxe pair of pajamas that the star may as well be headed off to bed.

At the Barclays Center 40/40 Club

I understand that the 40/40 club at the Barclays Center is more sports lounge than nightclub, but these cream-colored pajamas seem a smidgeon too casual.

In Pink Lace Live At A Concert

Forget bringing a cardigan to combat office air conditioning; a lacy negligee-inspired tunic is all the rage if Rihanna is to be believed.

Live In Performance

I suppose RiRi was at a loss for what to wear live in concert, because her bralette and cigarette-patterned suit seems to be missing something…

In Alaia At The 2013 Grammys

Could there have been a more perfect gown for Rihanna’s walk along the 2013 Grammys red carpet than this sweeping crimson Azzedine Alaia? I think not.

In Adam Selman At The 2014 CFDA's

Whatever mysteries remained about Rihanna’s body were revealed with this literally transparent Adam Selman gown, worn by the singer to the 2014 CFDA’s. And I thought the awards were about clothing, not a lack thereof.

At The 2014 MTV Movie Awards

Hugh Hefner would be proud, because Rihanna’s seductive robe, worn to the 2014 MTV Movie Awards, would fit right in at the Playboy mansion.

Front Row At Edun's Spring 2015 Runway

Rihanna clearly had to tumble out of bed and head straight to Edun, because this silky suit could easily be worn from day to night (and by night, I of course mean bed). However, it is quite a lovely set.