Bad Girl RiRi: Rihanna’s Style Evolution

Discovered in her hometown of Bridgetown, Barbados, signed to Def Jam Recordings and pumping out her first major hits all within that same year, a 16-year-old Rihanna began doing the rounds at industry events in 2005, with one of her first major red carpets being the World Music Awards.

Rocking a poofy mini-skirt and crop top, the singer is almost unrecognizable from the otherwise edgy music icon we know from today. The cutesy-styling was never quite a fit on the stunning singer, who would soon begin to explore her unique sense of personal style.

One year into the game and already topping the charts with her number one single, “SOS”, Rihanna took home the hardware for “Female Artist of the Year” at the 2006 Billboard Music Awards. For the big night, she stepped out in a risqué white mini dress and bold red lip.

Showcasing a shorter, sleeker hairstyle first debuted in her massive 2007 hit “Umbrella”, Rihanna was slowly but surely revealing her desire to break away from the “teen pop princess” role and find a more grown-up sound — and look — of her own.

Shining bright like a diamond at the 2008 BET Awards, Rihanna had reason to smile. Up for a slew of awards that evening, and fresh off her Grammy win, the singer sported a piecey pixie-cut and bright yellow gown with ruffle details.

Dressed to impress for the 2009 theme of “The Model as Muse”, Rihanna nailed it in a shiny suit with exaggerated shoulder details, bowtie and leather driving gloves. We love the unexpected look of a full suit on the singer, whose edgy hair and on-point makeup completed the ensemble for a memorable first Met experience.

Sometimes fashion risks pay off — and sometimes they miss the mark. While we can’t say we loved this Stephane Rolland white gown, we do give Rihanna props for taking a chance on a style she wouldn’t typically lean toward.

Rocking a glamorous, one-shoulder, feathered gown to the 2010 MTV Europe Awards, Rihanna looked all grown up and ready to spread her style wings. We love this glamorous and high-fashion side of the singer.

2011 was the year of Rihanna’s mega-smash hit “We Found Love” and we really felt that when she stepped out in this sheer-paneled white gown for the 2011 Grammy Awards. From the fiery-red hair to the perfect berry lip, we’re calling this funky look as one of her best.

Possibly one of our favourite years for Rihanna fashion, RiRi rolled into 2012 ready to rock any and every red carpet. From dark pixie haircuts and daring gowns, to big, voluminous blonde locks and lower-than-low cut dresses, all eyes were on her this year as everyone wondered, “What will she do next?”

While we love the bold pixie cut, we can’t say the same for the bizarre bra-and-skirt combo Rihanna wore to the 2013 American Music Awards.

In a sparkly sheer dress and fur shawl (we’re hoping faux!), Rihanna showed up and bared (almost) every inch of her figure for the 2014 CFDA Fashion Awards. Did we love the look? Meh. Do we respect every bit of this red carpet moment? Hell, yes.

Ladies and gentlemen: the dress that broke the internet. Love or hate it, this bubblegum-pink princess ballgown was all anyone could talk about for weeks after the event, launching a slew of imitation styles for the masses to scoop up.

In 2016, Rihanna released a surprise for eager fans in the form of her eighth studio album, “Anti”. Amidst all the red carpets of that year for the singer, some of her best looks were served during off-duty moments and fashion week photo-calls. This Christian Dior moment was easily one of our favourites.

We’re still not sure what to make of this bouquet-style ensemble that Rihanna donned to the 2017 Met Gala. From the mess of faux petals to the unflattering strappy red shoes, we’re just not board with this one, but kudos to RiRi for committing to this look, right down to the makeup.  

Launching her super-successful makeup line — Fenty Beauty — at Harvey Nichols in 2017, Rihanna was perfection in a voluminous purple strapless mini dress. We love how this pretty hue pops against her skin tone and pairs so well with show-stopping diamond accessories.

Attending the world premiere for her film Ocean’s 8 in 2018, Rihanna stepped out and showed up in a big way wearing something between a dress and an actual piece of art. This funky, almost fluid one-shoulder gown is perfection. Edgy, unexpected and unique, it’s the perfect fit for the star.

Rihanna is one of the few celebrities who’s as fun to watch off-duty as she is on the red-carpet. Doing her thing while out in New York in 2019, RiRi served up some serious on-trend style in an oversized blazer and silk slip dress. We’re here for it.

A seasoned couture-queen by now, the multiple award-winner looks stunning in a black gown with voluminous dropped skirt and intricate white underlay.

Starting the year off right, Rihanna is on-trend and proving that orange is, in fact, the new black. Yes, queen.

On February 22nd, Rihanna accepted the President’s Award at the 51st NAACP Image Awards, hosted by BET. Radiant in a voluminous purple mini dress, RiRi is definitely setting the stage for another stylish year ahead.