Kourtney Kardashian's Best Hairstyles Ever

As the oldest of the Kardashian clan and mother of Mason, Kourtney has a cool confidence that we love. Pair that with her casual yet chic Hollywood style, and she always looks fab. Check out her top 10 hair and makeup moments here, then see how they look on you with our Virtual Hair Makeover tool!

By Megan Cahn

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Side Part

Kourtney flips her long black hair over and shows off her killer smile at the Teen Choice Awards in 2009.
kourtney kardashian with her hair in a bun
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Ballerina Bun

Long eyelashes and rosy cheeks are the perfect touch to Kourtney's sky-high hairstyle at the Maxim Hot 100 Celebration in 2009.
kourtney kardashian with long wavy hair
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Luscious Waves

A pregnant and glowing Kourtney looks gorgeous with long, flowing, chocolate-brown hair and tan skin at the Emmy Awards in 2009.
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Flipped Out

Kourtney looks extra-sweet with soft makeup and shoulder-length shiny hair at the Leather and Laces Celebration in 2009.
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Pin Straight

Kourtney parts her long, straightened hair down the middle for a boho-chic look at Kim's Las Vegas birthday party in 2008.
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Half-Up 'Do

Kourtney's loose half-pony looks casual yet chic at Bravo's A-List Awards in 2009.
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Bouffant Pony

Kourtney stands out with a pompadour hairstyle and purple eye shadow at the Victoria's Secret Fashion Show in 2008.
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Silver Shadow

Kourtney's metallic eyeliner and long lashes are the perfect wild touch to her classic hair and lips at a poker tournament at the Playboy Mansion in 2009.
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Low Knot

Kourtney stands out with a unique hairstyle and nude lips at Rock the Vote in 2008.
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Natural Beauty

Kourtney looks carefree and beautiful with this low-maintenance look at a So So Def/Island Records party in 2008.
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