What You Need to Get Cara Delevingne's '90s Fly Girl Look

Before today’s rappers boasted about wearing Balenciaga, Maison Martin Margiela, and Tom Ford, performers like Aaliyah, Tupac, and TLC were rocking snapbacks, baggy jeans, and high-top sneakers in the ‘90s, revolutionizing the hip-hop fashion scene forever.

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  • No one was cooler than Will Smith’s Fresh Prince, who brought neon and Nike Jordans to Bel-Air, or In Living Color’s Fly Girls troupe, who danced to Wreckx-n-Effect’s “Rump Shaker” in tribal prints and crop tops. The decade’s influence is undeniable, inspiring Rihanna, Miley Cyrus, and Cara Delevingne to adopt this colorful, edgy style as their own recently. As such, we thought it was time to give your wardrobe a hit of fly appeal, so click through our slideshow to see how to look fresh all summer long.


  • DKNY S/S 13
    Photo credit: DKNY

    DKNY S/S 13

    The early ‘90s were all about excess, including giant logos plastered on just about everything. This season, DKNY brought back their iconic branding via the Black Cotton Onesie With DKNY Logo ($95) beneath a Silver Leather Jacket ($895).

  • Miley Cyrus
    Photo credit: MPNC/AKM-GSI

    Miley Cyrus

    R&B singer Aaliyah helped popularize the sultry tomboy look in sports bras and slouchy pants. Cyrus nails it in a KTZ Poet Embroidered Short Bomber Jacket ($276), T By Alexander Wang Leather Bralette ($375) and Ashish pants (which are half-sweatpants, half-denim) from the S/S 13 collection.

  • Rita Ora
    Photo credit: FameFlynetUK/FAMEFLYNET PICTURES

    Rita Ora

    Ora’s Katie Eary splashy Blue Seas Silk Shirt ($752) and matching skirt would have made Fly Girls like Jennifer Lopez and Carrie Ann Inaba proud.

  • Ashish S/S 13
    Photo credit: Ashish

    Ashish S/S 13

    Ashish’s collection was playfully irreverent and oh-so-‘90s, particularly the Oversized Shirt Dress With Sequined Numbers ($467) paired with denim shorts and sneakers.

  • Rihanna
    Photo credit: FameFlynetUK/FAMEFLYNET PICTURES


    Funky accessories give Rihanna’s outfit the TLC treatment, including her printed snapback, Elizabeth and James Limited Edition Valenti Sunglasses ($425, available in Shiny Black/Gold), Chanel lego bag, and Converse Chuck Taylor All Star Sneakers ($44) in Optical White.

  • Balmain S/S 13
    Photo credit: FirstVIEW

    Balmain S/S 13

    Door-knocker earrings, much like Balmain’s oversized Metal Circle Earrings ($322), were a trademark of hip-hip trio Salt-n-Pepa.

  • Giulia Baggini
    Photo credit: Getty Images

    Giulia Baggini of Giulia's Fashion Blog

    Baggini wears her Zara overalls (one strap down, of course) and Moschino Cheap & Chic tee dressed up with Spektre’s mirrored sunnies and Zara’s chunky pearl necklace.

  • Street Style
    Photo credit: Stockholm Streetstyle

    Street Style

    Chunky chain-link jewelry and denim jacket elevates this stylephile’s white top and jeans.

  • Aline Weber
    Photo credit: Stockholm Streetstyle

    Aline Weber

    Pops of neon, a graphic tee, and lace-up boots? The model nods to a handful of the decade’s best trends in a Marc Jacobs jacket, Stella McCartney t-shirt, One Teaspoon jeans, and AllSaints boots.

  • Street Style
    Photo credit: Stockholm Streetstyle

    Street Style

    Aside from basketball shoes, rappers in the ‘90s favored lace-up boots. This street style muse gets it right in Dr. Martens paired with a vintage jersey and acid-wash jeans.

  • Cara Delevingne
    Photo credit: Getty Images

    Cara Delevingne

    The British model shows her love for the ‘90s--literally!--in Minkpink’s 90’s Tunic Tank ($46), lace-up sneakers, and, of course, a backwards baseball cap.

  • Team Topshop’s Stripe Sleeve Sweatshirt ($45) in Green with a kicky skirt and Timberland boots.

  • The more chains the better right? Slip on Sara Designs’ Woven Chain Wrap Watch ($328) in Black/Gold for a watch and cuff bracelet all in one.

  • Your ensemble wouldn’t be complete without a pair of really cool black shades, such as Thierry Lasry’s Slutty Cat Eye Acetate Sunglasses ($564) in Black/White.

  • Commit to the overall look by styling Vision Streetwear’s Graffiti Print Tee ($60) in Multi with slouchy leather trousers.

  • Luxe, over-the-top clothes had a place alongside urban streetwear in hip-hop too. Remember Biggie’s Versace shades in his “One More Chance” video? Versus’ Printed Pants ($395) in Black Background offer the perfect homage to the late rapper.

  • Heavy gold chains were a style staple (everyone from P. Diddy to the members of N.W.A. were rarely spotted without them). We like Tom Binns’ take in the form of his statement-making Uber Urban Respect Necklace ($787).

  • Anyone who’s ever caught an episode of The Fresh Prince of Bel Air recalls Will Smith in an assortment of vibrant bomber jackets or windbreakers. We suggest snagging 3.1 Phillip Lim’s Embroidered Techno Jersey Bomber Jacket ($1395) in Multi-Blue for an equally punchy, fashion-forward look.

  • Nike’s Blazer Mid Mesh High Top Sneakers ($145) in Black are classics that go with everything.

  • Wear Bebe’s Chain & Stud Jewel Buckle Belt ($39) low on your waist over a ribbed tank top.

  • On the opposite spectrum of all the tomboy fashion in ‘90s hip-hop? Fly Girl style, which included sequined minis, leather bustiers, and body-conscious pieces, like Sparkle & Fade’s Mesh Block Bodysuit ($39).

  • We can’t get enough of the luxe quilting and gold accents (including a very appropriate chain strap!) on Lulu Guinness’ Small Patent Leather Clutch ($390).

  • Polish your outfit with Borsalino’s Baseball Quilted Faux Leather Hat ($137), worn backwards or titled to the side of course!

  • We love the Versace-inspired feel of Nasty Gal’s Lion Medallion Earrings ($20).  

  • Watch any of Snoop Dogg’s classic videos, from “Gin and Juice” to “Nuthin’ But A ‘G’ Thang”, and you’ll find him in baggy jeans. Avoid the sag but get just the right amount of slouch in the form of Current/Elliott’s The Boyfriend Jeans ($206) in Super Loved.

  • If you were a hip-hop act in the ‘90s--male or female--you flaunted brands like Nike and Adidas regularly. Display the latter’s famous three-stripe symbol with the Adilette Slides ($30) in Black/White.

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