Celebrity Style

30 Rihanna Outfits From The Early 2000s You Totally Forgot About

So. Many. Vests.

by Amy Sciarretto
Updated: 
Originally Published: 
rihanna outfits 2000s
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After first hitting the music scene in 2005, Rihanna quickly rose to pop icon status with back-to-back albums. Though she has taken an extended pause from dropping any new music since 2017 (*side eye*), she has remained in the cultural zeitgeist through her numerous business ventures — namely, Savage X Fenty and Fenty Beauty, not to mention the several collabs with brands like Puma.

After the mogul has finally dropped new music and announced she’ll be headlining the 2023 Super Bowl, I was inspired to take a trip down memory lane. I went down a '00s-era Rihanna wormhole, which revealed a plethora of incredible outfits I totally forgot about.

Today, Rihanna sets, defines, and defies trends every time she gets dressed. A decade ago, however, she was still cultivating her personal style — and it involved a lot of crop tops. Back then, RiRi's look was similar to established pop stars like Britney Spears, Beyoncé, and Christina Aguilera with bikini tops, capri pants, and denim skirts abound.

Rihanna would eventually evolve her look, making daring, high fashion looks her trademark. But back in the '00s? She played it a little safer — nothing like the edgy street style or dramatic red carpet looks she would be known for years later. Though she was still figuring out her vibe, there were plenty of moments in her early days that would hint at the fashion icon she would later become. Let's revisit them, shall we?

1. Bikini As A Top

Rihanna poses in the press room at the T4 Poll Winners' Party 2005 With Smash Hits at Wembley Arena ...
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This gold bikini top doubled as a shirt for this outfit. The glitzy, revealing look was giving big Deseny’s Child vibes. And peep the single glove to match.

2. Pin-Up Style

Singer Rihanna arrives at the 3rd Annual Vibe Awards on November 12, 2005 at Sony Studios in Culver ...
Frederick M. Brown/Getty Images Entertainment/Getty Images

Rihanna has always loved a mini dress (and still does). Back in 2005, she rocked this flared black and white skirt — an iconic ‘00s silhouette.

3. Cropped Vest

Singer Rihanna poses backstage during a MTV Networks Tempo Channel launch event at The Plantation & ...
Evan Agostini/Getty Images Entertainment/Getty Images

A vest and cuffed capris were the epitome of ‘00s style — trends I’m thankful stayed in that era.

4. Military-Inspired

Barbadian singer Rihanna pose after announcing the nominations for the 33rd Annual American Music Aw...
Vince Bucci/Getty Images Entertainment/Getty Images

Though she looks undeniably stylish, the military-esqe shirt dress was definitely toned-down by current Rihanna standards.

5. Cowboy Boots & Lace

Rihanna at the "Hope Rocks" Benefit Concert - August 13, 2005
John Sciulli/WireImage/Getty Images

The denim mini, the pewter cowboy boots, and the lacy babydoll tank? It’s giving “you’re watching Disney Channel.”

6. Sporty Street Style

Rihanna at the Madison Square Garden in New York City, New York
Jim Spellman/WireImage/Getty Images

Rihanna’s streetwear game is the strongest there is — even back in the 2000s, with this sporty top, baggy jeans, and sneaker combo.

7. Flared Miniskirt

Singer Rihanna performs on stage at the 2005 World Music Awards at the Kodak Theatre on August 31, 2...
Kevin Winter/Getty Images Entertainment/Getty Images

Her trumpet skirt and crisp white top isn’t a far cry from the Miu Miu set that would later take over the fashion industry. Good girl gone bad, indeed.

8. Casual In Cashmere

Rihanna at the Gala Opening of The JC Penney Experience on Broadway at One Times Square in New York ...
Stephen Lovekin/WireImage/Getty Images

This ivory sweater and brown boot moment positively screams ‘2000s fashion.’

9. All-Over Metallic

Musical guest Rihanna performs live on the plaza on NBC News' TODAY on June 8, 2007
NBC NewsWire/NBCUniversal/Getty Images

The artist’s early rock n’ roll looks included liquid metallic babydoll dresses and fingerless gloves.

10. Marilyn Monroe-Esque

Singer Rihanna poses in the press room after winning the award for Best Female Artist of the Year at...
Ethan Miller/Getty Images Entertainment/Getty Images

This frock — which looked a lot like Marilyn Monroe's infamous dress — was a harbinger of the sultry look Rihanna would eventually make her trademark. I totally forgot about this moment, but I still love it.

11. Nautical Details

Rihanna performs during the Jay-Z "Rock tha Block" tour at Rod Laver Arena October 28, 2006 in Melbo...
Kristian Dowling/Getty Images Entertainment/Getty Images

Her belted performance romper was actually really cute. I definitely copied this look in the ‘00s.

12. Houndstooth & Suspenders

Rihanna smiles after singing the National Anthem before the game between the New York Mets and the N...
Chris Trotman/Getty Images Sport/Getty Images

Raise your hand if you’ve ever felt personally victimized by a pair of 2000s-era suspenders.

13. Art Deco

Rihanna accepts the award for Favorite Soul/R&B Female Artist at the 2007 American Music Awards in L...
Ethan Miller/Getty Images Entertainment/Getty Images

The beauty entrepreneur rocked a tiered mermaid gown to accept her award as Favorite Soul/R&B Female Artist at the 2007 American Music Awards. NGL, I’d love to see her revive this baby today.

14. Dominatrix

Rihanna performs September 22, 2007 at the Molson Ampitheatre in Toronto, Canada.
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If anyone was surprised when Rihanna moved into the lingerie business, I’d direct them to this photo. Ya girl has been doing it right for years.

15. Mid-2000s Neons

Singer Rihanna poses backstage after an appearance on MTV's Total Request Live, June 11, 2007 in New...
Evan Agostini/Getty Images Entertainment/Getty Images

This highlighter yellow pant with a flared top is so aggressively mid ‘00s, it’s like looking back into my own closet.

16. Pastel Cupcake Gown

Singer Rihanna arrives at the 2008 BET Awards held at the Shrine Auditorium on June 24, 2008 in Los ...
Frazer Harrison/Getty Images Entertainment/Getty Images

This yellow Giambattista Valli dress, worn in 2008, is nothing compared to the yellow Guo Pei gown she wore at the 2015 Met Gala. I’m just sayin’.

17. Statement Shoulders

Singer Rihanna attends the launch of VEVO, the world's premiere destination for premium music video ...
Jason Kempin/Getty Images Entertainment/Getty Images

Check out those statement shoulders! This look seems wild now, but back then, this was culture in the making.

18. Shoulder Pads & Bandages

Singer Rihanna performs onstage at the 2009 American Music Awards at Nokia Theatre L.A. Live on Nove...
Kevork Djansezian/Getty Images Entertainment/Getty Images

Ahhh, the era of bandage dresses (and bodysuits, apparently). The nostalgia is real with this one.

19. Asymmetric Hemlines

Singer Rihanna arrives at Nokia Theatre L.A. Live on November 22, 2009 in Los Angeles, California.
Jason Merritt/Getty Images Entertainment/Getty Images

Her laser-cut, black and white dress is far away from the basic sweater and jeans she favored earlier in the decade. This is the Rihanna we know and love.

20. OG Barbiecore

Singer Rihanna poses for photographs backstage at MTV's Total Request Live show at the MTV Times Squ...
Scott Gries/Getty Images Entertainment/Getty Images

It’s no surprise that the Bad Gal was 15 years ahead of the Barbiecore trend. Here’s hoping she still has this little number in her closet.

21. Star Spangled

Singer Rihanna poses for a photo backstage during MTV's Total Request Live at the MTV Times Square S...
Scott Gries/Getty Images Entertainment/Getty Images

This starry halter dress feels so anti-Rihanna, it’s like looking at a totally different person.

22. Bold Cutouts

Rihanna at the Staples Center in Los Angeles, California Singer on February 11, 2007 in Hollywood, C...
Jesse Grant/WireImage/Getty Images

This one-shoulder Robert Cavalli gown was an early look at the jaw-dropping red carpet moments Rihanna would provide in the following decade.

23. Bubble Dress

Singer Rihanna, winner of Choice R&B Artist and Breakout, Female at the 8th Annual Teen Choice Award...
Jeffrey Mayer/WireImage/Getty Images

The bubble dress silhouette was definitely worn to my high school homecoming dance more than once. Naturally, Rihanna wore it better than most.

24. Leggings As Pants

Rihanna at the Pauley Pavilion in Westwood, California
Jeffrey Mayer/WireImage/Getty Images

The dress-over-capri-leggings combo is giving me flashbacks to high school — and it’s not pretty.

25. Punk Goes Pop

Rihanna attends 2008 American Music Awards at Nokia Theatre on November 23, 2008 in Los Angeles, CA....
Patrick McMullan/Patrick McMullan/Getty Images

I absolutely lived for RiRi’s punk era. This spiky, studded, covered-in-chains corset could easily be worn today. Ahead of the fashion curve, as always.

26. Fedora & A Waist Belt

Singer Rihanna performs onstage at the 8th Annual Teen Choice Awards at the Gibson Amphitheatre on A...
Kevin Winter/Fox/Getty Images Entertainment/Getty Images

Nothing says early ‘00s like a fedora and a massive belt. The elbow-length gloves have been brought back in 2022, but this Victorian-era button up can stay in the early aughts (sorry, not sorry).

27. Cherry Red Accessories

Rihanna at the Antonio "L.A." Reid Receives The UJA-Federation Of New York's Music Visionary Award -...
Jason Kempin/FilmMagic/Getty Images

I think we all had a pair of red, patent leather pumps during this era, so I can’t really fault her.

28. Babydoll Mini

Rihanna attends 2006 MTV Video Music Awards at Radio City Music Hall on August 31, 2006 in New York ...
Patrick McMullan/Patrick McMullan/Getty Images

I wouldn’t be mad if this glitzy fit-and-flare made its way back to the red carpet. CC: Rihanna’s stylist.

29. Bandage Dress

Rihanna arrives to the 3rd Annual Fashion Rocks Concert held Radio City Music Hall, New York City Se...
KMazur/WireImage/Getty Images

The bandage dress trend was everywhere in the 2000s, from the Kardashians to Rihanna herself. TBH, I kind of like this take on it.

30. Lingerie As Outerwear

Singer Rihanna performs on stage at the 13th annual MTV Europe Music Awards 2006 at the Bella Center...
Jo Hale/Getty Images Entertainment/Getty Images

Ending on this look felt appropriate, given Rihanna’s hugely successful lingerie brand. She always knows how it’s done.

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