1September 2002
Getty ImagesFive years before Keeping Up With the Kardashians premiered on E!, Kourtney hit up a fashion show afterparty in L.A. wearing a semi-sheer tank, black pinstripe pants, and a logo bag.
2April 2007
Getty ImagesJust ahead of the show's premiere, Kourtney wore this hot-pink bubble-hem piece, paired with gold earrings and heels, to a men's fashion show in L.A.
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3April 2007
Getty ImagesLater that month, at a Vegas party hosted by her sister, Kim, she wore this green and black dress that had a mesh modesty panel, pairing it with a black clutch and silver heels.
4October 2007
Getty ImagesKourt showed up to Kim's birthday party in L.A. wearing this white kimono dress with a plunging neckline, accessorising with a studded clutch and black strappy shoes.
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5August 2008
Getty ImagesFor the grand opening of a Hollywood sushi joint, Kourtney kept it casual in a pair of flared, light-wash jeans and a neutral silk blouse.
6September 2008
Getty ImagesSilk and flares were kind of her thing, actually. Not long after that, she was spotted in L.A. wearing this lilac and lace cami, paired with dark-wash bell-bottoms and bug-eye sunnies.
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7October 2008
Getty ImagesBy the next month, Kourtney was into wearing statement dresses. Check her out in at a Las Vegas event in this purple ombre fringe mini, which she wore with black platform Mary Janes and a gold bracelet.
8February 2009
Getty ImagesThe following year, she was still at it with an eye-catching patterned sheath, paired with an even more attention-grabbing oversize fold-over clutch.
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9June 2009
Getty ImagesKourtney stepped off a jet in a patterned blazer dress with a large black belt and coordinating heels, which she accessorised with a gold Louis Vuitton handbag.
10October 2009
Getty ImagesPregnant with her first child, Mason, Kourtney chose a form-fitting olive sheath, black pumps, and a statement gold necklace for the launch of Rich Soil's clothing collection at then-popular store Kitson in L.A.
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11October 2010
Getty ImagesThe new mum made an appearance at an event in NYC wearing this head-to-toe leather look with super strappy heels.
12February 2011
Getty ImagesAt a QVC event in New York, Kourtney worked the wide-leg pants trend in a pair of black trousers worn with an olive tank and a gold belt.
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13February 2011
Getty ImagesIt's here where Kourtney's style journey enters a wild phase. At a Las Vegas nightclub appearance, Kourtney wore this blush mini with a popping feather collar, a quilted clutch, and black pumps.
14September 2011
Getty ImagesSee what I mean by wild? Kourtney was way into animal print at this point in her life. She wore these leopard-print pants with a black cardigan, coordinating pumps, and a teal necklace at a Victoria's Secret Fashion Week event in NYC.
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15November 2011
Getty ImagesThe next month, Kourtney attended a Dollhouse book signing in L.A. with her sister Khloe, wearing a white blouse, a red skirt with suspenders, and these very distracting houndstooth tights.
16February 2012
Getty ImagesThe next year, while pregnant with her second child, Penelope, she attended the Elton John AIDS Foundation Academy Awards Viewing Party in West Hollywood in a much more simple look. She wore this flowing white gown with gold trim and accessorised with blingy gold bracelets, earrings, and a coordinating clutch.
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17September 2012
Getty ImagesNow a mother of two, Kourtney was spotted out and about in NYC wearing this polka-dot blouse, a black skater skirt, and a leather belt bag.
18February 2013
Getty ImagesAt the following year's Elton John Oscars viewing party, Kourtney went bold in this red floral ballgown, which she paired with black shoes and a simple gold bracelet.
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19May 2013
Getty ImagesWhile celebrating then-boyfriend Scott Disick's 30th birthday in Las Vegas, Kourtney (with a fresh set of bangs) showed up in this blue lace top and very funky feathered skirt.
20September 2013
Getty ImagesShe hopped on the cape-dress trend at an L.A. launch party for watch company Audemars Piguet in this hot pink number, which she styled with a black clutch and heels and a gold necklace.

Mylan Torres is Cosmopolitan.com's Photo Editor/Producer, where she curates the site's visuals for daily and long form stories, does photo research and produces photo shoots. Sometimes she even picks up a camera.

Rachel Torgerson is the fashion features and lifestyle director at Cosmopolitan, overseeing fashion and lifestyle coverage online, in print, and on our various social media platforms. She has over a decade of experience in the fashion and media industries. Before landing at Cosmopolitan as a digital fashion editor in 2016, she worked at Us Weekly, The Knot, and Fitness Magazine, among others. When she's not discussing runway trends, you can definitely catch her trying out (and, in many cases, failing) a new crochet cardigan pattern or in a spirited debate about the difference between the Bridgerton books vs the Netflix series. Follow her on Instagram and TikTok: @RachelTorgs
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