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  3. Rihanna's Most Risk-Taking Fashion Moments

Rihanna's Most Risk-Taking Fashion Moments

The pop star is the only girl in the world who could wear these over-the-top outfits like they're no big deal
By Emily Kirkpatrick
Updated February 20, 2018 08:50 AM
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LEATHER TRENCH 

60th Annual GRAMMY Awards - Show
Credit: Theo Wargo/WireImage

Rihanna experimented with the Matrix-inspired trend at the Grammy's by wearing a super-shiny brown Alexandre Vauthier Haute Couture patent leather trench coat as an off-the-shoulder dress with matching knee-high slouched boots and gloves (both also by Alexandre Vauthier Haute Couture).

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BEDAZZLED GUCCI SOCKS 

-18
Credit: Courtesy Rihanna/Instagram

If anyone could pull off the socks with heels trend it's Rihanna, with crystal $1,340 Gucci stocking socks no less.

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NOT SO VERY LOW-KEY TULLE 

rihanna
Credit: Rihanna/Instagram

What a casual Tuesday looks like for Rihanna: wearing a Giambattista Valli dress made completely out of blue tulle, sneakers and cool sunglasses.

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DENIM ON DENIM ON DENIM

Vogue's Forces Of Fashion Conference
Credit: Dimitrios Kambouris/Getty

There are very few people who can rock denim from head-to-toe and Rihanna is one of them in this Tom Ford ensemble.

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LBD 

Sephora Hosts Fenty Beauty By Rihanna Launches in Paris
Credit: Stephane Cardinale/Corbis/Getty

Rihanna's take on the classic LBD means being anything but classic.

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GOING FOR GOLD 

Fenty Beauty by Rihanna launch, Spring Summer 2018, New York Fashion Week, USA - 07 Sep 2017
Credit: Gregory Pace/Shutterstock

Rihanna absolutely nailed this season's biggest color trend (and we should all stop trying). She looked radiant in a yellow Oscar de le Renta ballgown that she paired with a cropped shirt in a matching golden hue for her Fenty Beauty launch.

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SHINE BRIGHT LIKE A DIAMOND 

rihanna-1-2000
Credit: Kevin Mazur/Getty Images for Fenty Beauty)

The singer really brought her shine factor to the Sephora launch of Fenty Beauty in N.Y.C. wearing a mini black dress adorned with shiny embellishments and over-the-knee sparkly boots.

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LILAC BABYDOLL DRESS

rihanna-2
Credit: David M. Benett/Dave Benett/Getty Images for Kendo

RiRi channeled her feminine side with this light purple Molly Goddard dress she wore to the launch of her Fenty Beauty line in London.

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LOUIS VUITTON DENIM 

rihanna
Credit: Charles Pitt/246paps/MEGA

An oversize Louis Vuitton x Supreme denim jacket, Balenciaga hat and bright blue hair just screams Bad Gal RiRi.

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RED CARPET LINGERIE

Stars attend the "Valerian" premiere in Paris
Credit: Splash News

We almost didn't notice Rihanna chose to wear a bra to the premiere of Valerian and the City of a Thousand Planets, because we were too busy staring at her standout pink sunnies and the sequin, fringe and feather adornments on her Prada two-piece ensemble.

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JANE MANSFIELD-CALIBER CLEAVAGE

rihanna
Credit: Karwai Tang/WireImage/Getty Images

The pop star balanced out her voluminous Giambattista Valli gown with a whole lot of sex appeal up top.

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RED CARPET PRINCESS

Premiere Of EuropaCorp And STX Entertainment's "Valerian And The City Of A Thousand Planets" - Red Carpet
Credit: Todd Williamson/Getty

Riri wore a gown worthy of a fairytale princess to the L.A. premiere of her new film Valerian.

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WILD, WILD, WILD, PANTS

Rihanna Films a Music Video With DJ Khaled
Credit: INSTARimages.com

Only the bad gal could make a totally sheer top and combination pant-boots look this nonchalant.

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FRESH OFF THE RUNWAY GUCCI

rihanna
Credit: Getty; Rihanna/Instagram

One person's totally unwearable outfit is Rihanna's low-key Coachella lewk.

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BIG AND TALL MENSWEAR

The 69th Annual Parsons Benefit
Credit: Jamie McCarthy/Getty

The singer channeled the Talking Heads' David Byrne in this super oversized suit.

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UNCONVENTIONAL CANNES

"Okja" Red Carpet Arrivals - The 70th Annual Cannes Film Festival
Credit: Dominique Charriau/WireImage

Of course, Riri had to give the Cannes red carpet her own unique twist, pairing her white Dior gown with a teeny-tiny pair of sunglasses.

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ROCKET MAN CHIC

'Rei Kawakubo/Comme des Garcons: Art Of The In-Between' Costume Institute Gala After Party at 1 OAK
Credit: Splash News Online

No that's not Elton John stepping out of the club, it's just Barbados' baddest.

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MET GALA CHAMPION

"Rei Kawakubo/Comme des Garcons: Art Of The In-Between" Costume Institute Gala - Arrivals

This is a woman who knows how to dominate even a red carpet packed with the biggest style stars on the planet, showing up this year in a Comme des Garçons sculptural floral explosion.

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DENIM CENTAUR

*EXCLUSIVE* Rihanna is sexy in denim at Kendrick Lamar's Coachella Performance
Credit: Roger/AKM-GSI

If Britney Spears circa the 2001AMAs had a baby with a centaur, Riri in this outfit would undoubtedly be the result.

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GREY GARDENS HYPEBEAST

Celebrity Sightings in New York City - March 23, 2016
Credit: Robert Kamau/GC Images

Rihanna brings you Little Edie realness with a streetwear twist.

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ELF HEELS

2017 Roc Nation Pre-GRAMMY Brunch
Credit: Kevin Mazur/Getty

A white linen jodhpur would be enough of a fashion risk for your average woman to handle, but Rihanna takes it one step further adding on a pointy, white elf shoe.

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TRACKPANT HOOD AND MATTRESS COAT

Rihanna on the set for "Paper" magazine photo shoot in LES, NYC
Credit: Splash News

We want to say this isn't a thing, but get back to us two years from now when we're all wrapping our hair up in trackpants and wearing floor-length mattress coats.

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TOP TO BOTTOM TRENDS

Rihanna steps out in a $5,000+ street style look
Credit: AKM-GSI

Mastering a single trend is no longer a challenge for someone like Riri, which is why she likes to go all out with her lewks, accidentally inventing five new style crazes in the process.

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SANTA CLAUS BELT

Rihanna arrives to Giorgio Baldi in LA
Credit: Pap Nation/Splash News Online

It's a rare woman who can borrow a belt from Santa's closet and make it look nonchalant.

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MAXI MAXI DRESS

harry-rihanna-2-1333x2000
Credit: Chris Jackson/Getty Images

Rihanna doesn't just throw on jeans and sweats when she wants to go low-key - she swathes herself in tons of print fabric and adds super-strappy heels.

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BLACK TIE ATHLEISURE

30th FN Achievement Awards
Credit: Bill Davila/Startraks

Regular athleisure is so 2015. This year, it's all about black tie athleisure or bust. After all, if your sportswear doesn't come with a bedazzled Juicy opera glove and tons of diamonds, what's the point?

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TEES THAT WILL BLOW YOUR MIND

Celebrity Sightings in New York City - November 8, 2016
Credit: Raymond Hall/GC Images

Only a true icon can wear a T-shirt that instantly gets turned into another T-shirt, which then turns into a meta Inception-style fashion moment when she wears the finished product.

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GIANT PUFFER

EXCLUSIVE: Rihanna went to studio for Puma Shooting advertising
Credit: KCS Presse / Splash News Online

Pants do feel a little irrelevant when you're wearing a puffer coat that's three feet thick.

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MARIBOU BRA AND FISHNETS

Image
Credit: Theo Wargo/Getty

Lil' Kim has got to be furious she didn't get her hands on this maribou-trimmed bra first.

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IRL HEART EMOJI

Celebrity Sightings in New York City - September 5, 2016
Credit: Robert Kamau/GC Images

Who but Rihanna could manage to make the heart emoji look ... kind of sexy?

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TINKERBELL PROM DRESS

TUTU CUTE
Credit: AKM-GSI

It's not fair-y that no one but Rih could look so cute in electric green tulle.

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DENIM CHAP BOOTS

Rihanna wears Princess Diana T-shirt

She actually managed to make chaps a thing. Enough said.

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CUPCAKE COUTURE

Image
Credit: Jon Kopaloff/FilmMagic

Have we mentioned Rihanna's a bit of a maximalist?

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FUR ON FUR

Image
Credit: 247PAPS.TV / Splash News Online

A fur stole worn as a belt over a fur mini dress on a balmy 40-degree night? Why not.

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BLUE LIPSTICK

RIHANNA
Credit: Michael Loccisano/Getty

Showing off frostbitten lips before Queen Elsa made them cool.

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NEXT LEVEL PJ DRESSING

Rihanna in see-through bra

Giving us a TLC "Creep" moment in a silk robe, pajama pants, and sheer lace bra.

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NEON GREEN THIGH-HIGHS

RIHANNA
Credit: Frazer Harrison/Getty

While everyone's now wearing thigh-high boots, are they neon green thigh-high boots with perfectly coordinated matching accessories? We didn't think so.

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SCARF TOP

Image
Credit: Courtesy Rihanna

Pro FENTY Tip: Your Hermès scarf can always double as a very tiny top in a pinch.

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BATGIRL

Image
Credit: FameFlynet

Solving crimes has never looked so chic.

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3D NIPPLE EMBELLISHMENT 

RIHANNA
Credit: Jason Merritt/Getty

Who needs pasties when you can have 3D breast ornaments designed by Tom Ford (that were inspired by you in the first place)?

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BEDAZZLED NAKED DRESS

RIHANNA
Credit: Dimitrios Kambouris/Getty

The only appropriate ensemble for a woman about to accept a CFDA Fashion Icon Award is a dress that's not really a dress at all.

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"FEAR" STOLE

RIHANNA
Credit: Rex USA

While everyone else is still wearing statement tees, Riri's already moved on to a statement fur stole.

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FUR INSTEAD OF A SHIRT

SHEER TALENT
Credit: INF

No shirt? No problem. That fur wrap is probably warmer than most of her usual tops anyway.

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CRUELLA COUTURE

SECOND COAT
Credit: Splash News Online

A very '80s mob boss's wife moment just for a change of pace. (She liked the sweatband veil so much, she later made her own.)

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ALL CAMO EVERYTHING

Rihanna leaving the Bowery Hotel wearing an all-camouflage outfit in Soho, New York City
Credit: NorthWoodsPix / Splash News

If there's one thing Rihanna doesn't know how to do, it's blend in.

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SHEER SKIRT

Rihanna flashes a peek after a dinner at Giorgio Baldi
Credit: AKM-GSI

For when you're feeling conservative, but still want to show off a little bit of everything.

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LITTLE BO PEEP LINGERIE

Grammy after party at Club Anti, Los Angeles, USA - 13 Feb 2017
Credit: Owen Kolasinski/BFA/REX/Shutterstock

Our only question is: What is the storybook shepherdess supposed to wear now that the pop star has clearly raided her lingerie drawer?

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BEJEWELED BRAS

Rihanna jumping in Zulu International Band, Kadoom

While these types of bras are a staple at every West Indian Day parade, only on Rihanna do they look like just another casual aspect of her ever day apparel.

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MILE-LONG TRAIN

Image
Credit: Rabbani and Solimene Photography/Getty

And finally, a train isn't truly a train unless it requires three men to help you carry it up the Met Gala steps.

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    Skip slide summaries

    Everything in This Slideshow

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    View All

    1 of 49 LEATHER TRENCH 
    2 of 49 BEDAZZLED GUCCI SOCKS 
    3 of 49 NOT SO VERY LOW-KEY TULLE 
    4 of 49 DENIM ON DENIM ON DENIM
    5 of 49 LBD 
    6 of 49 GOING FOR GOLD 
    7 of 49 SHINE BRIGHT LIKE A DIAMOND 
    8 of 49 LILAC BABYDOLL DRESS
    9 of 49 LOUIS VUITTON DENIM 
    10 of 49 RED CARPET LINGERIE
    11 of 49 JANE MANSFIELD-CALIBER CLEAVAGE
    12 of 49 RED CARPET PRINCESS
    13 of 49 WILD, WILD, WILD, PANTS
    14 of 49 FRESH OFF THE RUNWAY GUCCI
    15 of 49 BIG AND TALL MENSWEAR
    16 of 49 UNCONVENTIONAL CANNES
    17 of 49 ROCKET MAN CHIC
    18 of 49 MET GALA CHAMPION
    19 of 49 DENIM CENTAUR
    20 of 49 GREY GARDENS HYPEBEAST
    21 of 49 ELF HEELS
    22 of 49 TRACKPANT HOOD AND MATTRESS COAT
    23 of 49 TOP TO BOTTOM TRENDS
    24 of 49 SANTA CLAUS BELT
    25 of 49 MAXI MAXI DRESS
    26 of 49 BLACK TIE ATHLEISURE
    27 of 49 TEES THAT WILL BLOW YOUR MIND
    28 of 49 GIANT PUFFER
    29 of 49 MARIBOU BRA AND FISHNETS
    30 of 49 IRL HEART EMOJI
    31 of 49 TINKERBELL PROM DRESS
    32 of 49 DENIM CHAP BOOTS
    33 of 49 CUPCAKE COUTURE
    34 of 49 FUR ON FUR
    35 of 49 BLUE LIPSTICK
    36 of 49 NEXT LEVEL PJ DRESSING
    37 of 49 NEON GREEN THIGH-HIGHS
    38 of 49 SCARF TOP
    39 of 49 BATGIRL
    40 of 49 3D NIPPLE EMBELLISHMENT 
    41 of 49 BEDAZZLED NAKED DRESS
    42 of 49 "FEAR" STOLE
    43 of 49 FUR INSTEAD OF A SHIRT
    44 of 49 CRUELLA COUTURE
    45 of 49 ALL CAMO EVERYTHING
    46 of 49 SHEER SKIRT
    47 of 49 LITTLE BO PEEP LINGERIE
    48 of 49 BEJEWELED BRAS
    49 of 49 MILE-LONG TRAIN

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