Rihanna's 18 Best Beauty Looks (Including Some You May Have Missed)

Full disclosure: It’s nearly impossible to pick winners when it comes to Rihanna’s beauty looks. There are, after all, a lot to consider. First, we had to narrow down her best red-carpet moments, from the demure to the daring. Then, there are the looks she sports when off the clock, whether hitting a Clippers game or just running around New York. (Did you really think she just throws on some mascara and pulls her hair into a topknot before leaving the house? Not a chance.)

So after a lot of hunting, we (somehow) landed on 18 that we, personally, love best — just in time for her birthday today. You may disagree with the retrospective, but know that we tried our best to sift through the wealth of gorgeous, striking, edgy, eye-catching hair and makeup that Barbados’ golden girl has rocked through the years.

So without further ado, here is a (small) fraction of RiRi’s awesome appearances.

Photo: Jon Kopaloff/FilmMagic/Getty Images.
Proving obvious roots can look at home on the red carpet, Rihanna matched her dark growth with sooty, sultry eyes. She also demonstrated that, contrary to popular belief, curly haired girls can totally pull off bangs.
Photo: Larry Busacca/ Getty Images.
Rihanna brought it back. Way back. To the '20s. Her slightly scandalous take on the flapper look (naked or nah?) was best paired with a shine-bright-like-a-diamond headwrap and slicked-down sideburns. And when you’re already looking the part of the sexpot, why not go with a smoky eye?
Photo: NBC NewsWire/ Getty Images.
Early in her career (2007 to be exact), Rihanna dipped her toe into what would become a passion for striking hair colors. Before she went mad for magenta and gaga for grey, she edged into unnatural hues with deep purple streaks that accented her sleek bob.
Photo: Jason Merritt/Getty Images.
Rihanna proves she isn’t always trying for something outrageous. Here she pulls off something classically glamorous — red lips and loose waves — to perfection. She managed to make an otherwise meh look appear totally fresh. Maybe it’s the neon red lipstick she matched to her dress.
Photo: NCP/ Star Max/ GC Images/ Getty Images.
The dream of the '90s is alive in Rihanna, even if she was but a tween at the time. For a bodega run in New York, she matched her grunge-inspired dress with vampy lips and a disheveled, high ponytail (revisiting a previously worn style is so unlike her).
Photo: Stuart Wilson/Getty Images.
Usually it takes feats of engineering and a multitude of bobby pins to create a side sweep that stays put, but Rihanna solved the problem by simply shaving one side of her head. In the process, she sported a style that was impossibly edgy and elegant at the same time. Punk on one side and prom on the other?
Photo: Noel Vasquez/ Getty Images.
Sure, this was most definitely a wig, but there are two reason why this is amazing: One, she reasoned that cotton candy pink hair was fitting for a basketball game; and two, she matched it to her purse. It’s a wonder the players could even focus on the game...or maybe that's just us.
Photo: Kevin Mazur/ WireImage/ Getty Images.
Even when Rihanna keeps makeup and hair fuss to a minimum, she still looks like a woman with a vision. Her close-cropped locks appear as if she ran some gel through them and called it a day but, of course, they manage to look awesome. Mostly, we noticed her envy-inducing glow, which is lightly enhanced but otherwise all her, paired simply with lush lashes and a little liner.
Photo: Josiah Kamau/ BuzzFoto/ Getty Images.
What could otherwise be a throwaway topknot is made extraordinary thanks to an eye-popping blue color. Perhaps only Rihanna could manage to make vivid cobalt locks look so casual. Never a dull moment with this one.
Photo: Jeffrey Mayer/ WireImage/ Getty Images.
Another short cut we can’t get enough of is this piece-y pixie that Rihanna showed off at the 2012 MTV VMAs. Her lopped locks made her long lashes look extra lengthy (okay fine, those are definitely falsies). And the ruby red lips? The cherry on top.
Photo: Samir Hussein/ Getty Images.
It would be fair to say Rihanna convinced those who play it safe to attempt blue lipstick...
Photo: Kevin Mazur/ Getty Images.
By now, you are aware of Rihanna’s affinity for a red lip. She loved it so much she had MAC whip up a ri-vised (get it?) version of its cult favorite Ruby Woo. With her go-to lip, she amped up the sex appeal with a hot side flip and waves that suggested she’d recently had a roll in the hay.
Photo: Jon Kopaloff/ FilmMagic/ Getty Images.
If you’re going to go monochromatic, picking orange is a bold move. But Rihanna is just that kind of girl. She wore a particularly juicy hue on her lips, a wash of carrot on her lids, and a similar shade on her cheeks — though the makeup isn't particularly brave when you consider she’s basically wearing pasties up top.
Photo: Karwai Tang/WireImage/ Getty Images.
Rihanna accessorized her painstakingly constructed Guo Pei couture gown with a similarly swirly headpiece for the MET Gala last year. Her sleek bob mirrored the curves thanks to upturned ends; and perhaps as a counterpoint, her brows were made stick straight and sharp as a tack by makeup artist Mylah Morales.
Photo: NCP/ Star Max/ GC Images/ Getty Images.
Rihanna’s love affair with red hair covered an array of hues within the color family. She went crimson, cherry, burgundy, and, as pictured, had a brief fling with copper. She decided on two tones here: A matchy-matchy beauty look (red on red) paired with her matchy-matchy navy ensemble.
Photo: James Devaney/ GC Images/ Getty Images.
When the '90s turned up as a trend, the most standout beauty look to come out of that was the brown lip. Here, Rihanna picked a cocoa shade that’s practically twinning with her hair. On that note, we’re digging the veritable fountain of ringlets emerging from the top of her head.
Photo: Paul Archuleta/ Getty Images.
What to pair with a gown that screams, “I’m a lady!” when you’re bad girl RiRi? Sleek, expensive-looking hair extending down to your back, which clearly indicates you have an unlimited extension budget. (And a smoky eye that’s made outré by way of red and white shadows, too!)
Photo: Dominique Charriau/ WireImage/ Getty Images.
Rihanna toned it down for Dior's couture show is Paris last year, both in dress and beauty. But as is her way, she added her own edge to otherwise minimal makeup by going with a pale, mauve lip. Her elaborate updo is befitting of someone about to witness a parade of six-figure frocks.
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