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When it comes to originating street style trends, Rihanna can be considered the OG. And while her latest fashion moments revolve around a baby bump, it’s impossible to forget another one of the musician’s steadfast accessories from years past — a wine glass. In 2016, photos of Rihanna carrying stemware out the door heavily circulated the internet, and she finally addressed her reputation as “wine glass thief” on The Graham Norton Show two years later, while doing press for Ocean’s 8. “My mom is gonna see this,” she laughed as the UK talk show host flashed a series of her going-out looks across the screen, each one finished with a glass of alcohol.
In actuality, the move complements her boundary-pushing aesthetic. Rihanna is constantly experimenting with mixed-media pieces, skin-revealing slits and stilettos, and tough, oversize streetwear, usually constructed with the help of stylist Jahleel Weaver. While it’s been some time since the 35-year-old mom-of-two has been snapped by the paparazzi swapping an obligatory purse or iPhone for wine, those outfits are still fodder for inspiration — especially during party season. The songstress, businesswoman, and self-made billionaire even fronts the spring/summer 2024 Louis Vuitton men’s campaign pregnant, holding four monogrammed duffles and a casual to-go coffee. While that might make for a tasteful change in beverage, Rihanna’s attitude is just as fierce; her carefree glamour pertinent as ever.
Ahead, we’ve rounded up Rihanna’s best street style finished with a drink, pinpointing some of her wardrobe must-haves for you to shop along the way.
Marking one of her most memorable wine glass outfits circa 2015, Rihanna casually brought her drink outside of a recording studio in New York City. Her baby pink satin pajamas, worn open over a lace bralette with a number of body chains and a Fenty nameplate, were just as bold. And the outfit wouldn’t have been complete without feathered mules, proving the musician was way ahead of the pajamas-as-outerwear trend that still feels fresh today.
Make your mark in J.Crew’s feather-strap heels, which come in this dark mauve shade — a nod to Rihanna’s taste — or black. The rhinestone-adorned buckle is a subtle detail that makes these shoes feel all the more special.
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Underwire offers more support if you’re game to wear lingerie outside of the house. Try the trend in this affordable bra that’s also available in red, black, and pink.
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Stepping out to promote her Fenty x Puma line at New York Fashion Week in 2016, the fashion savant layered a zip-front velour maxi dress over lace-up knee-pad boots that were memorably debuted on her runway. She held a glass of champagne to celebrate the moment on the go, as one does.
Slip into a luxe jacket-dress like Rihanna’s that can be worn with tights, heels, or boots. You won’t regret investing in a season-less piece like this with timeless tailoring — it’s a party season staple.
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While Rihanna’s Fenty x Puma boots can be considered fashion treasure (they’re still being resold on eBay), you’ll achieve the same vibe in this Jeffrey Campbell iteration with a stiletto heel and slit at the back of the knee for functionality and movement.
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In 2017, Rihanna accessorized her deconstructed denim outfit with a Peroni for the Kendrick Lamar set at Coachella. She styled a Matthew Adams Dolan jacket with front-slit pants that revealed a pair of cream Maison Margiela boots. Finishing the outfit with structural Adam Selman x Le Specs sunglasses and a Dior crossbody bag, the bottle of beer certainly contributed to her spin on festival season denim.
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This maxi slit dress has the same oversize attitude as Rihanna’s slouchy denim and could easily give way to a statement shoe moment.
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While sightseeing in Prague in 2016, Rihanna flaunted a double-slit white ribbed halter dress by Faustine Steinmetz, styled with a Balenciaga logo stole draped over her left shoulder — directly drawing attention to the wine glass in her hand. Walking tall in Vetements sock boots, she added to the sporty appeal with suave gold shield sunglasses. “I took that back to the hotel that I took it from,” Rihanna said of her stemware on The Graham Norton Show in 2018.
Lucky for us, a few Balenciaga fur stoles like Rihanna’s are still available for a marked-down price. Drape yours over a single shoulder for an evening out, or tie it firmly around your neck while bundling up in winter.
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Go for the frame-less look on top in transparent gold sunglasses crafted from acetate.
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When Rihanna was asked whether she was granted permission to leave the club with the above glass, she explained that it actually might have been hers. “That might have been one that I took to the club,” she surmised. “It’s crystal!” The look in question is from 2013, and Rihanna is pictured exiting the Dream Downtown hotel in New York City. Clad in a sparkly, plunging black minidress, the star played up the glamour with a diamond choker, matching chainmail bracelet, and simple black sandals.
I’m partial to Zara’s fringe and sequin minidress for parties, especially since, considering all the trimmings, the LBD is a one-and-done outfit in and of itself — no further accessorizing is necessary.
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If you’re one to max out on shine, this glass crystal embellished choker rings in at a wallet-friendly price point and offers a take on the popular 3D-floral trend, which has trickled down from runways like Loewe, Carolina Herrera, and Zimmermann.
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Rihanna recently shared her spring/summer 2024 campaign for Louis Vuitton Men, which is a continuation of her bold maternity style. The multihyphenate poses here in an oversize leather button-down with a pixelated graphic print clasped solely at the bust, so her shirt drapes open across her bump. Perhaps as a nod to her beverage-toting days, or rather as a suggestion that Rihanna can do it all with her hands full, she grasps a to-go coffee in her right hand.
