Rihanna has artfully represented a spectrum of incredible style. Some would classify her as a peacock dresser, but she is also very intentional and often calculated in the way she styles herself. Throughout that cycle, she somehow manages to remain mysterious, which leaves her audience and fans in a constant state of famine—we are always wanting, even demanding, more.

What’s great about Rihanna is through her fashion and styling, she makes people feel empowered, as if we could manifest the same confidence as her in the way we present ourselves to the world. From her early portfolio of fashion collaborations to being the first Black woman to design under LVMH, she has proved herself one of the greatest fashion forces of our generation. And to honor that, we've compiled her best, most influential outfits from the past 10 plus years.  

BET 106 & Park Appearance

When: 2008

When Rihanna first came out around 2005, her style wasn't bad—she, like a lot of other celebs, loved an Herve Leger dress—but it wasn't distinctive. She was 17 years old and figuring herself out as an artist and a young woman. But by the time she released Good Girl Gone Bad in 2007, and started working with stylist Mariel Haenn, her aesthetic was coming into focus—we also must credit her early hair stylist Ursula Stephen. This look she wore to promote Good Girl Gone Bad (Reloaded) on BET's 106 & Park introduces us to a sexy, flirty, and confident Rihanna. The black jacket and mini skirt are elevated with these Balenciaga gladiator sandals designed under creative director Nicolas Ghesquiere, which were a must-have item at the time.—Aria Hughes

MET Gala 2009

When: 2009

For her first MET Gala in 2009, Rihanna opted to wear this Dolce and Gabbana tuxedo with biker gloves and platform pumps—the theme that night was "The Model as Muse: Embodying Fashion." Here we see the pop star’s penchant for menswear and a her evolving pompadour. Not wearing a dress to the MET Gala was a risk. But this look, along with her hair, lent Rihanna an edge and point of differentiation.—Aria Hughes

Gramercy Hotel 2009

When: 2009

Exaggerated shoulders were a thing around this time and Rihanna delved deep into the trend without looking costumey or too of-the-moment. We see that reflected in this outfit, which includes a black and white Gareth Pugh jacket with a corset-like bodice, broad shoulders, matching white gloves, a black mini skirt, and Louboutin pumps. —Aria Hughes

Echo Awards 2010

When: 2010

For the 2010 Echo Awards, which is Germany’s biggest music awards ceremony, Rihanna wore a green jumpsuit with accentuated shoulders and cape details that she paired with nude Louboutin pumps. Created by Alexandre Vauthier, a designer Rihanna continues to wear today, the jumpsuit gave us a glimpse at what would be a Rihanna signature: a plunging neckline that would later reveal her Goddess Isis chest tattoo.—Aria Hughes

Airport Look

When: 2012

Around the 2010s, Rihanna became a walking billboard for streetwear brands like Trapstar, Crooks & Castles, Married to the Mob, Supreme, Vision Streetwear, and more. This look embodies that era. Here we see her wearing a Trapstar hoodie and T-shirt, a customized Opening Ceremony OC Patch Varsity Jacket, and a pair of Nike Air Yeezy 2s. —Aria Hughes

New York City

When: 2012

It wouldn't be the 2010s without a Givenchy graphic T-shirt, and with this outfit, that also includes Tom Ford over-the-knee snake skin boots, we start to see a sleeker style from Rihanna. That has to do with Mel Ottenberg, a stylist she started working with for the "Loud" tour in 2011. Ottenberg told the New York Times: “My whole thing was she’s so beautiful, she’s so over the top, she doesn’t need so much stuff. We can strip it down."—Aria Hughes

River Island Launch

When: 2013

Rihanna's first fashion venture was with River Island, a fast fashion retailer based in the U.K., which launched in 2013. The collections were full of Rihanna's wardrobe staples at the time: oversized T-shirts, sweatsuits, hoodies, and bomber jackets along with sexier pieces like body-con dresses and mini skirts. She designed the collection with her stylist Mel Ottenberg and designer Adam Selman. The most memorable piece from the line were these layered denim pants she's wearing with a crop top.—Aria Hughes 

'Fashion Killa' Video With ASAP Rocky

When: 2013

ASAP Rocky tapped Rihanna for his "Fashion Killa" video, which was directed by Virgil Abloh. The song centers on Rocky, who was styled by Matthew Henson, rapping about a fashion-inclined love interest. Therefore, casting Rihanna was obvious. The video speaks to a very specific moment in the 2010s when Rihanna's role as a fashion icon was crystalizing and Rocky was starting to make his mark. In the video Rihanna starts off wearing a Supreme jersey and skinny jeans, then changes into a floor length, zebra print Tom Ford dress and lace veil headpiece with cat ears.—Aria Hughes


Chanel Fall/Winter 2014 Women's Show

When: 2014

Rihanna was killing it consistently during Paris Fashion Week Fall/Winter 2014 and one of our favorite looks from that season is this Chanel ensemble, which was a fresh take on the brand's classic tweed suit. The crop top, corset bodice, skirt, fanny pack, and matching sneakers embody Rihanna’s sporty and fun style—and also the late Karl Lagerfeld's ability to refresh what was once a stodgy fashion house.—Aria Hughes

Jean Paul Gaultier Fall/Winter 2014 Women's Show

When: 2014

Another significant look from that season was this Jean Paul Gaultier ensemble that included a see-through lace top, a fur stole with a pattern that matched the lace—it's a woman's face, by the way—wide leg trousers, and leather gloves. What else is there to say?—Aria Hughes 

CFDA Awards 2014

When: 2014

In 2014 Rihanna received the “Fashion Icon of the Year” award by the Council of Fashion Designers of America. “Even as a child I remember thinking, she can beat me, but she can’t beat my outfit,” she famously said in her acceptance speech. And so far, that notion hasn't been dispelled. The exhibit worthy outfit was created by the head of her then design team, Adam Selman, and was meticulously crafted out of 230,000 Swarovski crystals. While revealing just enough—but not too much—the full look included matching gloves with a matching headpiece and a pale pink fur stole by Pologeorgis. And she wore Manolo Blahnik metal gold chaos ankle strap sandals. This look will go down in fashion history for the craftsmanship behind it, the praise it garnered, what it represented that night, and Rihanna herself.—Scarlett Newman

Pre-Grammy Party

When: 2014

This canary shade of yellow suits Rihanna, as we've seen here and here. But this particular silk dress she wore to Clive Davis' Pre-Grammy gala hit all the right notes. Designed by Alexandre Vauthier—it was featured in his spring 2014 collection—its plunging neckline and hip-high slit is casual, sexy, and glamorous. The thing about Rihanna is she rarely looks like she's trying or uncomfortable in her clothes. Two important traits most fashion icons possess.—Aria Hughes

Alexander Wang for H&M

When: 2014

It was completely unexpected that a God-tier star like Rih would rock high street fashion like this Alexander Wang X H&M two piece. It was an accessible look that let us take part in Rihanna’s fashion legacy without maximizing all of our resources. The grey-toned athleisure fit also included a pair of New Balance 574 sneakers. I saw Rihanna wearing Alexander Wang for H&M, so I went out and bought Alexander Wang for H&M (true story).—Scarlett Newman

White House Visit

When: 2014

Channeling her best Oliva Pope, Rih dropped by the White House for a private tour back in 2014 and decided to wear a dress by Stella Jean, a black designer based in Italy. Coming from her Autumn/Winter 2014 collection, the body of the dress features an Ankara print, while the pinstriped sleeves and collar give off the illusion that she’s wearing layers. While dressing more conservatively for this important outing, she kept it high fashion with Manolo Blahhik ankle strap sandals in black suede.—Scarlett Newman

MET Gala 2015

When: 2015

In what’s now her most memorable red carpet moment to date, Rihanna famously stepped onto the 2015 Met Gala red carpet in a beaming yellow cape-gown designed by Chinese couturier, Guo Pei. The 55 pound dress took around 20 months to construct. Underneath, she opted for a custom pink bustier by Agent provocateur and wore a pair of triple-strap muse pumps by Christian Louboutin. The Guo Pei moment will go down  in history as one of THE top 10 MET looks.—Scarlett Newman

'Good Morning America' Appearance

When: 2015

No one does the color pink quite like Rihanna. Here she is in head-to-toe Pascal Millet doing the promotional rounds for the animated film, “Home,” which was released back in 2015. She enlists a bit of old Hollywood glamour (a la “What A Way To Go”) with a corresponding pink fur and paler hued Christian Louboutin pumps to pull together a timeless monochromatic look for the ages. Rihanna seems to reserve the color pink for launches, premieres, and other big events, so you know when she steps out in the girlish hue, it’s going to be major.—Scarlett Newman

Vintage Sean John Velour Track Suit

When: 2015

She followed up that pink Pascal Millet outfit with a pink vintage Sean John velour set that she wore with Degen shoes and a Dior bag. It was a nice homage to Puffy's brand that peaked before Rihanna became famous. It seems like Rihanna has a penchant for urban streetwear brands. According to the New York Post, Rihanna purchased vintage dealer Gabriel Head's entire archive of Baby Phat.—Aria Hughes

iHeartRadio Music Awards Performance

When: 2015

Rihanna as a pimp hopping out of a helicopter? Yes, please. This look was the perfect choice to perform her song "Bitch Better Have My Money" at the iHeart Music Awards. She's wearing a black Adam Selman dress, and green boots, fur coat, choker, and sunglasses that are all by Versace.—Aria Hughes

On the Street in SoHo 

When: 2016

One of the greatest things about following Rihanna’s style escapades is that she graces casual situations in very, very expensive clothes. For instance, feeding birds after a night of clubbing in a $15,000 Saint Laurent Heart Cape on a mild autumn evening. The coat was a part of Hedi Slimane’s final collection at Saint Laurent Paris and symbolized his love for the fashion city.  She’s usually the quickest to debut the most coveted items shown during fashion month, which typically breeds the question, “How did she get that so fast?” She completed the look with denim shorts and her (then) signature “Riri” heels by DSquared.—Scarlett Newman

Bergdorf Goodman Puma x Fenty Launch

When: 2016

Here we see Rihanna moving on to her second major fashion collaboration with sportswear brand Puma. The Fenty x Puma Creeper was the best seller from the partnership—because of Rihanna, Puma's sales lifted—but we can't forget about the apparel. Rihanna made athleisure pieces feel elevated, as showcased with this Puma x Fenty outfit she wore to launch the collection at Bergdorf Goodman. The cropped baseball T-shirt with bell sleeves, the cut-away track pants, and the thigh high boots show Rihanna's evolution as a designer and business woman.—Aria Hughes
 

Hillary Clinton T-shirt

When: 2016

As Rihanna has gotten older, she's been more outspoken and active about things that don't involve music but benefit the greater good. She understands how big her platform is and how to use it responsibly. Here we see her doing that by sporting a Trapvilla Hillary Clinton T-shirt, supporting the candidate before the 2016 election—Rihanna later wore a T-shirt of her wearing this shirt. She styled it with a pair of denim cut-off shorts, brown Timberlands, and the Louis Vuitton x Frank Gehry Twisted Box Bag, which she sports often.—Aria Hughes

MTV VMAs 2016

When: 2016

In 2016, Rihanna received MTV’s Video Vanguard Award. And as opposed to performing one long medley of her hits, she graced the stage four separate times, with four separate looks and elaborate production set ups. All of the outfits were amazing, but the custom made, pink Hood By Air get-up she wore to intro the show was special. It honored a black designer, Shayne Oliver, who had, much like Rihanna, dominated the cultural zeitgeist during the 2010s. And visually, the pink look combined with an all pink set and pops of red, was graphic and impactful.—Aria Hughes

Anti Tour

When: 2016

Throughout her career, Rihanna's mastered giving just enough to her fans, but she loosened the valve with her album Anti, which seemed to represent exactly how she wanted to sound and look at that particular moment. For the tour, which was styled by Mel Ottenberg, she steered clear of sequins and leotards—what most artists were wearing on stage—and presented four memorable looks coming in mostly neutral colorways that sometimes included dramatic, hooded, billowing cloaks that she would take off to reveal the rest of her look. She wore brands like Craig Green, custom pieces from Adam Selman, Armani Prive, Giuseppe Zanotti, etc. We love this chocolate brown suit with strap up details in the back from Y-Project and custom leather corset by LA Roxx. It could be an homage to Madonna's iconic tour outfits designed by Jean Paul Gaultier. But whether it is or isn't, Rihanna's look is just as influential.—Aria Hughes

JFK Airport

When: 2017

Rihanna's airport fits merit a list unto themselves, but something about this Chloe shearling coat that she paired with a white tank top, relaxed-fit jeans, Louis Vuitton backpack, diamond necklace, and brown Timberlands feels too '90s hip-hop and hood rich to not include. You can get a better shot of the outfit here.—Aria Hughes

Paris Fashion Week Spring/Summer 2017

When: 2016

While in Paris during fashion week she stepped out in a heavenly oversized quilted puffer that looked like it had been spun at the hands of angels, but in fact, it was created by Swedish School of Textiles grad, Ella Boucht. She kept the look on-trend with a Vetements graphic tee that read “You fuck’n asshole,” and killer custom pink slingback pumps by RoSa. Statement coats aren’t for the faint of heart, but Rihanna uninhibitedly brings them to life.—Scarlett Newman

Grammy Awards 2017

When: 2017

Rihanna loves volume, and she somehow always pulls it off. This look is Armani Prive, meaning it's couture, and it features a voluminous organza ball skirt and a crystal embellished crop top. But the best thing about this look is probably the blinged out flask that kept making appearances throughout the night. Whether she's wearing couture from Armani or denim cut-off shorts, Rihanna is Rihanna.—Aria Hughes

Meetings in New York

When: 2017

While traipsing around NYC for a day of meetings, Rih stepped out in an oversized Y/Project blazer from their Spring/Summer 2018 Menswear collection  that she worn with a pair of light washed and distressed Levi jeans. She amped up the business casual ensemble with the Olgana Paris “Celeste” mink fur mule sandals, the infamous Louis Vuitton twisted box bag (designed in collaboration with Frank Gehry), and a pair of Roberi & Fraud “Betty” shades. The executive realness we love to see.—Scarlett Newman

Parsons Benefit 2017

When: 2017

Back in 2017, the Parsons School of Design honored Rihanna for her style, philanthropy, and endless support of rising designers. For the benefit, she wore a flesh-toned, oversized pantsuit by Parsons alum, Matthew Adams Dolan, who she’s been a fan of since he graduated in 2014. The cream colored, snakeskin Manolo Blahnik heels provide just enough color to not pull focus from the monochromatic suit.—Scarlett Newman

MET Gala 2017

When: 2017

Up until this point, we had seen Rihanna in many forms, but never anything as experimental or avant-garde then at the 2017 Met Gala, honoring Rei Kawakubo and Comme Des Garcons. Rih wore a look from the CDG Fall/Winter 2016 runway and matched it with kabuki-inspired, vividly colored makeup around the perimeter of her face. Her thigh-high version of the Dsquared Riri heel gave off an element of seduction that balanced the chaos of the garment. This moment proved that she really is a champion of all types of fashion and that she’s someone we can trust in to take risks on the red carpet that end up making history.—Scarlett Newman

Met Gala After Party

When: 2017

After wearing that amazing conceptual piece from Comme Des Garcons, it's no surprise Rihanna decided to slip into some pajamas for the MET Gala after parties. She took this route again in 2018. Here's she's wearing Gucci sunglasses, a feather trimmed Prada top, Prada sandals, and not one but two snakeskin belts. The following year Rihanna would launch her own lingerie and pajama line, Savage x Fenty. We continue to see a throughline with what Rihanna wears and businesses she pursues. Her style has helped support all of that.—Aria Hughes

Dior Cruise 2018

When: 2017

Here Rihanna fittingly blends into the backdrop of Las Virgenes Canyon, Calabasas, with colors and textures that compliment the natural elements of the desert. Serving us wild, wild west, she subtly blends the high culture of fur with the everyman vibe of relaxed jeans and lace-up hiking boots (Dior Homme Spring 2017). She’s the girl’s scout leader of our dreams. She’s the “Desparado” she so passionately describes on the Anti track. For Rihanna, it’s a rarity that such high-styling would include a pair of jeans, but it echoed the theme of the show and its location (jeans were originally popularized out west). We can have a little something different. As a treat.—Scarlett Newman

Coachella Day Two 2017

When: 2017

Wearing a look straight off the runway is typical for Rihanna. While out in the deserts of Coachella Valley, she shook the world in this head to toe crystal encrusted bodysuit that featured distressed jean shorts and a Gucci tank from the Fall 2017 collection. Rihanna is fun to watch at Coachella as she epitomizes the antithesis of her sartorial surroundings.  At some point in the night she even committed to wearing the sparkling face attachment with a pair of square framed Gucci shades. Her boots were from her own Fenty X Puma Spring 2017 collection, completing the edgy look.—Scarlett Newman

Vogue 'Forces of Fashion' Summit

When: 2017

Rihanna has donned a few all denim outfits over the years, but the Tom Ford one she wore to speak at the Vogue “Forces of Fashion” summit, which took place in October 2017, is next level. The set includes an oversized denim jacket, denim mini skirt with a matching belt, and knee high denim boots with a white heel and toe cap. And the green tinted glasses with the hair blowing in the wind? Perfection. By this time Jahleel Weaver, who used to assist Mel Ottenberg, is styling Rihanna for most events. —Aria Hughes 

Barbados Crop Over Festival

When: 2017

Rihanna has graced us with multiple Barbados Crop Over costumes. But we’re particularly fond of the vibrant look she wore in 2017. The teal wig mixed with the rhinestone fishnets mixed with the multicolored feather piece mixed with her womanly body is all perfection.—Aria Hughes

Coachella Day Two 2018

When: 2018

There's only a few people, let alone celebrities, who can pull off the more conceptual looks that brands like Y/Project produce. So it's exciting to see Rihanna wear them, and it's even more exciting to know that she wore this look to Coachella amongst hordes of people dressed up in denim shorts, flower crowns, and some non-descript crop top. Here Rihanna is wearing the Belgium-based brand's sheer camel dress along with is thigh high boots it made in collaboration with Ugg. Rihanna's IG caption reads "extra af," and we happily welcome the dramatics.—Aria Hughes

Coachella Day Three 2018

When: 2018

In another highly-styled, unorthodox Coachella look, Rih hit the desert in a sinister schoolboy getup (that coincidentally features another face mask) that indicates she’s probably gonna get into something a little rebellious for the evening. From the waist up she’s in Gucci Fall/Winter 2018 (what is it about Gucci that screams “festival chic” to Rihanna?) and below she’s wearing snakeskin pants by Elizabeth Weinstock (best known for her use of exotic skins) and matching boots by Rochas that definitely fit the desert vibe.—Scarlett Newman

July 4th in Barbados

When: 2019

Touching down in Barbados for the 4th of July, Rihanna is spotted getting off the plane in the Fenty “Immigrant” screen printed tee. She released the shirt as a part of her 6-19 Fenty Collection and told The Cut, she “hopes it will remind people that there are a million Rihanna’s out there getting treated like dirt.” Her travel style included the Palace sweatpants that she’s known to love along with a pair of white Air Force Ones.  She accessorized with Fenty “Antisocial” shades, a Louis Vuitton monogram vintage scarf around her neck, and the Louis Vuitton X Takashi Murakami “Boite Pharmacie” train case.—Scarlett Newman

Book Launch at the Guggenheim

When: 2019

Rihanna launched “The Rihanna Book” at the Guggenheim Museum in a leopard print dress with cut-outs by Saint Laurent Paris. She completed the look donning slouched knee-high snakeskin boots also by the famed fashion house. As much as we rag on celebrities rocking head-to-toe looks straight off the runway, Rihanna is obviously one of the only exceptions to the unwritten rule and somehow elevates the designer’s own interpretation of the look. The modern cut of the dress allows her to get away with an '80s-esque, heavy ruching of the boots. The lady is a V-A-M-P, VAMP. Period!—Scarlett Newman

BET Awards 2019

When: 2019 

In June 2019, Rihanna presented Mary J. Blige with the Lifetime Achievement Award at the BET Awards in a shapely biker jacket with fitted, flared leather pants to match as well as a fanny pack to complete the fit.  It’s easier to spot a Fenty look nowdays as the brand designs with prominent shapes and silhouettes in mind, like with this particular leather jacket. She is a huge fan of the Manolo Blahnik ankle strap sandals, pictured.  Rihanna is fashion’s superhero, so why not take a few notes from The Dark Knight with this vibe?—Scarlett Newman

Niece's Birthday Party

When: 2019

For her niece's birthday, Rihanna arrived in an edgier piece, that somehow managed to fit perfectly with it’s Barbie theme. In this cotton and tulle Quetshe shirt she evokes a girlish, childlike vibe--a perfect fit to celebrate a birthday. The shirt includes two abstract tulle designs in black at the top and a soft purple that hangs off the shirt like a dress.  She secures the casualty of the outfit with a pair of high waisted Jeans by Matthew Adams Dolan and completes the birthday fantasy look with Cinderella-esque Amina Maudi pumps that resemble a modern-day glass slipper.—Aria Hughes
 

New York City 2019

When: 2019

There’s a few important  things happening with this luxe yet leisure outfit. Firstly: It looks great. Rihanna has mastered the comfy, cozy, rich bitch fit—and it being all-white makes it look even more expensive. Then there’s the coat, which is from (Old) Céline’s pre-fall 2018 collection. That’s the last collection designed by Phoebe Philo, who built a cult following for the brand as its creative director from 2008 to 2018. And then there’s the sunglasses, which come from Rihanna’s LVMH-owned Fenty brand. For a while, these sunglasses were the only Fenty product the public saw before the brand’s launch in 2019. And the white Fendi bag, the Cuban chain choker, and Stampd sneakers complete the look.—Aria Hughes

Vacation Look

When: 2019

We can't compile Rihanna's best outfits without including a vacation look. The Bajan queen is familiar with a beach or a private resort, and her holiday outfits typically include a two piece swimsuit, lots of body jewelry, and bold accessories—remember this ski lodge look?!?. But we have to pay homage to this slow-motion Instagram post of Rihanna wearing an ASAI dress, the Bottega Veneta pouch bag, and Fenty sandals. We appreciate her generosity.—Aria Hughes

British Fashion Awards

When: 2019

In “The Prelude Pathétique” (2011) Lady Gaga prophesizes the impact the color Mint will on high fashion. Fast forward to 2019 at The British Fashion Awards in London, where Rihanna is drenched in the delicate shade of green courtesy of her own fashion house, Fenty. It’s another instance where she’s able to tap into certain elements of old-Hollywood glamour that are relevant to her own tier of stardom. The jewels around her neck (which actually connect to a series of jewels going down her back) are the perfect amount of ice to complement the opulence of the look overall.—Scarlett Newman

Diamond Ball 2019

When: 2019

Philanthropist Rih Rih. Since 2014, Rihanna has held an annual Diamond Ball Gala for the Clara Lionel Foundation, a nonprofit organization the pop star founded in 2012. Funds raised by the foundation go towards causes such as climate change, education, and emergency preparedness. For the most recent gala, she wore a Fall 2019 Givenchy couture gown designed by creative director Clare Waight Keller. The black velvet turtleneck dress with a mermaid tail and exposed boning towards the hemline is conservative, but still sexy. We're seeing a more grown up and sophisticated Rihanna, which is quite fitting for the occasion.—Aria Hughes

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