Jackson Lee/Splash News Online

Never one to play it safe, Rihanna hit the streets with a daring new look, and we don’t mean her minidress and laser-cut thigh high boots. Check out all those heavy blonde highlights! It’s almost the flip of Drew Barrymore’s dark tips on her blond bob. We always enjoy seeing what Rihanna is up to next, and we love that she’s lightening up for fall. Tell us: What do you think of Rihanna’s blonde streaks? Do you love them or hate them?

Ace Pix

What would Fashion’s Night Out be without some shoe shopping? Rihanna, Rachel Bilson, Katy Perry and Michelle Trachtenberg partied up a storm while shopping for shoes at designer Giuseppe Zanotti’s Upper East Side boutique. Rihanna, clad in a clingy black hooded dress by Cover and Giuseppe Zanotti for Balmain booties, pursued the shelves of shoes with girlfriends and her stylist Mariel Haenn. After settling on a pair of suede leopard-print wedges, the singer and designer himself hit the dance floor rocking out to “Last Dance” by Donna Summer. An onlooker tells PEOPLE, “I’ve never seen anyone dance and laugh so much at a fashion party before in my life!” Bilson skipped out on the dance party to try on close to twenty pairs before walking away with ankle booties and wedge sandals. And while Rachel played dress-up, Trachtenberg and Taylor Momsen made friends with Perry before picking out their own new shoes. Michelle settled on a pair of over-the-knee embossed leather boots, and Taylor stuck to her ’90s grunge style with crystal-encrusted flat biker boots. No word yet on what Katy took home, but we are sure they are just as drool-worthy as the rest. Click here to see where more stars partied on fashion’s biggest night out, and be sure to follow us on Twitter at Twitter.com/StyleWatchMag for all the latest Tweets from the Fashion Week!– reporting by Hitha Prabhakar
 

Gardiner Anderson/Carlos Vila/Bauer-Griffin

Rihanna’s fashion-forward sense of style has always been razor-sharp — and now she’s got a do to match. The singer debuted her closely shaven look in Manhattan last night, with freshly buzzed sides that have a similar vibe to Cassie’s half-shaven head. Is this the latest trend in Hollywood? Tell us: What do you think of Rihanna’s newest look? Would you copy her look?

Kevin Mazur/WireImage

Big news in celebrity fragrances — representatives for Parlux, the company that produces Paris Hilton and Jessica Simpson’s scents, confirm to PEOPLE.com that Jay-Z, Rihanna, Kanye West and a yet-to-be-announced “well-established female artist” have inked a fragrance deal with Jay-Z’s licensing company Iconic Fragrances. Both Rihanna and Kanye will launch signature scents in the summer of 2010, with Jay-Z and the mystery star following suit in 2011. For his part, hip-hop mogul Jay-Z is looking forward to the to expanding his empire, saying in a statement, “We are excited for the opportunity to partner with Parlux and their management team in the launch of these dynamic new brands.” Parlux’s CEO Neil Katz continues, “We are extremely excited to begin work on our projects with Rihanna and Kanye West. Each is an extremely highly regarded celebrity at the top of his or her profession who is undoubtedly going to make an indelible impression in the fragrance industry, just as each has done in the entertainment world.” And it seems that the stars are just as confident about the impending success of the scents. In an unusual move, they will receive payment in royalties, profit sharing and Parlux stocks rather than cash. And while there’s no word yet on who the mystery artist is, Parlux dismisses the idea that the star in question is Beyonce when speaking with WWD.

Frank Micelotta/Getty; VT/SJ/Splash News Online

We thought Beyonce’s metal glove was already an over-the-top look, but we spied the singer sporting some pretty wacky sunglasses while filming her lastest video for “Diva” this weekend. Check out that metal fringe! But apparently, out-there eyewear is the newest fashion trend for stars, because Rihanna performed at the American Music Awards this weekend in a bejeweled eyepatch. Now we want your opinion! Tell us: Which star’s eyewear is more outrageous? Rihanna or Beyonce?

Ever wonder what it’s like to be the face of a major ad campaign? Go behind the scenes with Rihanna, who is the face of Gucci’s UNICEF 2009 holiday ads, as she works with Gucci Creative Director Frida Giannini. This e-film documentary showcases Rihanna and Frida on the set of the UNICEF 2009 holiday ad campaign, Rihanna at the Gucci Winter Ready-to-Wear show in September, Rihanna and Frida discussing sketches and more. Check out this exclusive preview now, in anticipation of the full-length which will be posted on Rihanna’s and Gucci’s websites on December 9. Later this week, Rihanna and Frida will also be on hand at New York’s Grand Army Plaza for the annual snowflake lighting.

Courtesy Gucci

Rihanna and Gucci are giving us a sneak peek of the singer’s ads for the brand’s 4th annual campaign to benefit UNICEF. And talk about looking good while doing good! The series of ads, which won’t hit magazines in December, feature the singer modelling luxe goods from Gucci’s “Tattoo Heart” collection. A portion of proceeds from the all-white line will go towards improving the lives of children in sub-Saharan Africa through life-saving programs. And the singer couldn’t be happier to continue her work with the charity. “The work that UNICEF does in the world is so incredible,” she says. “And I am honored to be able to join forces with Gucci to create this amazing campaign which will contribute to UNICEF. I think the campaign and the sales of these beautiful products can make the difference.” Click here to learn more about UNICEF.

Evan Agostini/AP

We knew it was only a matter of time before this style-setter turned celebrity designer — after all, she’s already one of PEOPLE’s Best Dressed. While attending the Gucci Spring 2009 show in Milan, Rihanna, who has already done charity T-shirts with H&M and designed umbrellas for Totes, admitted to WWD that a clothing line is in the works, “I’m not one to rush into anything. I want to take my time. I can’t say when it will be released, but it’s definitely going to happen.” That’s good enough for us! With her girly spin on rock n’ roll style, we are sure Rihanna is gearing up to be the next Gwen Stefani. Tell us: Are you excited about Rihanna’s line?

Courtesy In Style

In the August issue of In Style magazine, which hits stands this Friday, cover girl Rihanna opens up about her rule-breaking fashion philosophy — and her future. While her non-conformist sense of style sets her apart from the crowd, she tells the magazine it’s all about having fun and staying true to herself. “I love to play to both sides of my personality — the girlie and the tough. That’s what makes my style different.” And taking her own path sometimes garners unexpected attention, especially when it comes to that famous short bob. “The first time I heard people were asking for the Rihanna, it was really flattering and maybe a little strange. It caught be by surprise, but now I feel it’s a very cool thing. I don’t feel the pressure to change it up again at all. I like it, as they like it.” At just 20 years old, the singer sees her future approaching fast, telling the mag, “I feel like I have so much more to accomplish before I’m 21.” But what about a decade down the line? “In 10 years I want to have already started my family and have some business of my own. A fashion line, a makeup line, and I still want to be doing what I’m doing at a much bigger capacity — by the grace of God!” Click here for behind-the-scenes footage of the cover shoot, and get the full interview in In Style, just in time for the weekend.

Evan Agostini/AP

At just 20 years old, Rihanna is one of the world’s most successful young singers, and yet again she’s using her fame to help those less fortunate. Gucci has just announced that the “Umbrella” chanteuse will be the face of an ad campaign that showcases their collaboration with children’s charity UNICEF. The ads, entitled Tattoo Heart, will feature the singer wearing limited-edition Gucci tattoo-heart-motif products, with 25% of sales being donated to the charity, WWD reports. It’s not the first time the singer has worked with UNICEF and Gucci. In February she performed at the design house’s star-studded Madonna-hosted fundraiser Raising Malawi, whose goals fit well with those of her own charity, The Believe Foundation, which she founded in 2006 to bring food and medicine to children in need.

Andreas Branch/PatrickMcMullan.com/Sipa

Hollywood’s most stylish stars turned out this week to celebrate a great combination: Gucci and Rihanna. Guests like Sophia Bush, Nicky Hilton, Zach Braff, Camilla Belle and Rashida Jones mingled at the elegant rooftop lounge, ABH, atop the Thompson Beverly Hills Hotel and dined on luxe fare. And the party’s guest of honor couldn’t have been happier. “It’s really nice,” she told PEOPLE of being honored. “Gucci is here, and we support each other.” But the singer’s superstar supporters were just as honored to receive an invite. “I am a big Rihanna fan,” One Tree Hill star Sophia Bush told PEOPLE. “She’s really one in a million, and at the level she is, she is so sweet and genuine and kind,” while Jones gushed, “I’m excited to meet her! She’s really cool. So beautiful and so talented.” But hanging out with the singer wasn’t guests’ only reward. Long tables lined with Gucci shopping bags were filled with an extra-special surprise — all the ladies at the event were gifted with Gucci’s much-coveted Hysteria Clutch.

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Credit

She’s one of music’s most stylish stars, and in a revealing new interview, Rihanna dishes about her fashion obsessions and favorite beauty tips — as well as her tomboy past. “I’ve been a fashion fanatic since I was little, looking at all the international magazines. But I used to dress like a boy when I was a kid,” she admits to the British edition of In Style. “I’d wear my brother’s baggy pants and his trainers.” And her tastes have definitely changed over the years. “Now I like little skull caps, jeans, flat boots that come up to the knees. And then I play around with the top — a big T-shirt, or a sleek camisole, or a jacket. I love jackets! I have a million.” The singer gives credit for her unique fashion sense to her makeup-artist mom. “She knew everything about perfume, skincare and make-up,” she says. “She never let me wear make-up but I was secretly fascinated, so when she’d leave home, I would play around with hers.” And her surprisingly simple secret to looking fresh-faced even on a grueling world tour? “Water and rest for my skin,” she says.

Jason Kempin/wireimage.com

Looking as amazing as ever, Rihanna donned over-the-knee boots by Steve Madden during her recent performance at the Atlantis in Paradise Island. And while the fashion chameleon continues to pull off every trend with complete chic, she’s not the only celeb trying out the look! Hilary Duff and Kate Moss have been stepping out in thigh-high boots, too — see our Trend Gallery. We’ve tracked down Rihanna’s boots as well as some similar styles to let you get the look for less.

Get Rihanna’s Boots!
For Real:
Steven by Steve Madden’s suede over-the-knee Frankie boot, $400, is available at select Steven by Steve Madden stores.

For A Steal:
Steven by Steve Madden leather over-the-knee boot, $259 at victoriassecret.com

Steve Madden’s patent over-the-knee Refrain boot, on sale for $126 at stevemadden.com

Spiegel’s suede over-the-knee wedge boot, on sale for $70 at Spiegel.com

Bauer-Griffin

We’ve already confessed that Rihanna is our latest fashion crush. And yet again, the singer struck a fashion high note — leaving her New York hotel toting this Kooba bag that accessorized her biker-chic look. Her Heather shoulder bag, trimmed with vivid day-glo piping, has a retro ’80s vibe that we love. You can order the same one, $465, at kooba.com, or nab a smaller version, the Bennie clutch, for a more affordable $295. And you’ll definitely be in good company — Jessica Biel, Jessica Alba and Hayden Panettiere have also been spotted carrying Kooba handbags.

Landov

Whether it’s gorgeous gowns or funky street style, an edgy bob or a tomboy crop, Rihanna is a fashion standout who can do no wrong in our eyes. Her funky fashion sense has her strutting in skinny jeans, bold patterns and sky-high stilettos. But with the flip of a switch, she can turn up the glam with stunning couture pieces, like this Jean Paul Gaultier jacket. “We both want every look to make a statement,” says her stylist Mariel Haenn. “She’s able to pull off a wide range of looks.” With all of the love we have for the beauty from Barbados, we have to admit that we definitely have a fashion crush on Rihanna. Now, just in time for Valentine’s day, the editors of StyleWatch magazine want to know whose style gets your heart a-fluttering. Tell us: What star do you have a fashion crush on and why?

Dave Allocca/Startraks

Rihanna has quickly become a major trendsetter, and now she’s using her icon status for good! The singer turned up to H&M yesterday to help launch the H&M Fashion Against AIDs collection, including a T-shirt she designed. The singer tells PEOPLE that she got involved because “I felt like young people need someone who they can look up to and relate to, and I felt that if I’m going to have such an impact on people I need to make it positive.” And as for her choice of slogan on the T-shirt? The singer explains, “Believe is the name of my charity. Believe and Youth Aids, they both cater to young people and educate them and empower them, so I thought I’d put that name on my shirt.” As for her style, she tells us that she definitely loves her collection of necklaces best — “I will give my shoes to my friends, but I always keep my jewelry” — and looks to Sienna Miller as a fashion inspiration — “I think her style is very street, very New York and kind of 80s. I love it. Everything she wears looks good to me.” Well, we’d say the same thing about Rihanna! For more information on the campaign and how to purchase Rihanna’s t-shirts or others designed by Timbaland, Good Charlotte and more, click here.

INF

Rihanna is earning quite a reputation as a platinum artist — and as a style chameleon! We can barely admire her newest haircut or makeup look before she tries another equally stunning option. No wonder she’s our StyleWatch cover girl this month! The singer debuted another ‘do this weekend at the NRJ awards in France — this time, a short pixie cut with long jagged bangs. We think Rihanna looks amazing no matter what her style is, but we want to know what you think! Tell us: Do you love Rihanna’s new short look? Or did you like it more with another style like her trend-setting bob?

Click here to see all of Rihanna’s best looks from 2007!

Mark Allan/WireImage

Rihanna’s spent the past year touring around the world — and she’s shown off a different look in just about every locale. We’ve put together our top 10 favorite hair and makeup looks of hers from 2007, including everything from old-school glamour in London to urban chic in NYC. Click here for the beauty trendsetter’s 10 landmark looks of the year.

Courtesy Seventeen

We certainly think Rihanna is a style icon on the making — who else could change their look so many times and have it work so well? — and Seventeen agrees with us! The singer is on the magazine’s December cover and is honored inside for being in their Style Awards. Rihanna tells Seventeen that she’s always been into fashion. “Well, I love playing with fashion. I’m very spontaneous — the best outfits from me come from not thinking about it. When I was growing up in Barbados, I actually learned about fashion from reading magazines and tearing out stuff that I thought was hot.” And of course, she keeps getting ready for big events fun by hanging out with her girls. “I always turn the music on. I just blast it. And it’s always fun when my girlfriends are around! You do each other’s makeup and each other’s hair, and you help each other pick out clothes. That’s the fun part. It’s more fun getting ready than actually being at the party.” Other trendsetters honored are Vanessa Hudgens, Jessica Alba, Jordin Sparks, Fergie, Lauren Conrad, Ashlee Simpson and Lil Mama.

MARK CHILTON/RICHFOTO/GLOBE; Jeff Kravitz/FilmMagic

Rihanna turned out in not one, but two jaw-droppingly, gorgeous looks at the at the World Music Awards in Monaco this weekend. First, she stole the spotlight on the red carpet in a curve-hugging D&G fishtail dress. The emerald green color looks amazing against her skin and her bright red lips and nails finish it off to perfection. After the show began, she switched into a flirty party frock for her performance. While some of the singer’s onstage looks are a bit much for real-life, this short and sexy dress is a total winner. The singer paired her adorable dress with lace gloves for an edgier look — a nod to Madonna perhaps? We’d skipped the gloves, but would love to add both dresses to our wardrobe. Tell us: Do you like the Rihanna’s sexy green dress or sweet party frock better?

See more looks from the weekend in our Daily Hit or Miss gallery.