The Coolest and Easiest Way to Wear Thigh-High Boots This Fall/Winter

The streetwalker stigma associated with wearing thigh-high boots is no more. Maybe we have this decade’s It girl Rihanna to thank for that? When she started pairing thigh-high boots with oversized t-shirts, she broke down the shoe style’s stripper barrier and crossed it over to the exclusive VIP territory of street-style swag.

Rihanna big shirt thigh high bootsRihanna leaving a building in New York City on October 1, 2012; catching a tube in London, England, on March 27, 2012; arriving at the Cuckoo Club in Mayfair, London, England, on June 15, 2013; performing at Ziggo Dome in Amsterdam, Netherlands, on June 23, 2013

Pretty soon, other cool chicks of Hollywood were doing it. Kylie Jenner said it herself that it was Rihanna who inspired her, who then inspired big sis Kim Kardashian to try the big-shirt-with-thigh-boots look in a photo shoot.

Kylie Jenner big shirts thigh high bootsKylie Jenner wearing oversized tops with thigh-high boots in Instagram snaps posted on July 20, August 8, and September 6, 2014

Cara Delevingne, Karrueche Tran, Lindsay Lohan — the list of fans keeps growing and growing. Spotted most recently sporting the style was Fergie, who loved the look so much she wore it both to the airport and to the event she was to attend.

Kim Karrueche Cara big shirts thigh bootsKim Kardashian’s Instagram pic from her Hype Energy USA shoot posted on August 18, 2014; Karrueche Tran’s Instagram pic from her guesting on the Just Keke show posted on July 9, 2014; Cara Delevingne heading to a house party at a private residence in Notting Hill, London, England, on February 16, 2013

Delilah Fergie Keisha big shirts thigh bootsDelilah at The Forum for Rihanna’s performance of her 777 tour in London, England, on November 19, 2012; Fergie at day 2 of the 2014 iHeartRadio Music Festival in Las Vegas, Nevada, on September 20, 2014; Keisha Buchanan at Steam and Rye in London, England, on May 10, 2014

If you ever find yourself questioning whether you could pull off thigh-high boots or not, take it from these ladies: just grab your dad’s/brother’s/boyfriend’s big T-shirts and go. Is there a cooler and easier way to rock thigh-high boots than this?

Below are our over-the-knee boot recommendations for this fall/winter. Check out our previous list of 20 black OTK boots that you will love for more pocket-friendly picks.

Thigh high bootsL to R: GUESS “Dandra” Thigh-High Boots, $149 / Luichiny “May La” Platform Thigh-High Boots, $109.95–$139.99 / Pleaser “Raven-8826/B/LE” Flat Thigh-High Boots, $135.95–$140.80 / ZiGiNY Lace-Up Thigh-High Boots, $199.95

Credit: Kylie Jenner, Kim Kardashian, and Karrueche Tran's Instagram, Neil Warner/Stuart Castle/Will Alexander/Bridow/WENN

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