Penelope’s love affair with Western boots dates back to 2015. Her first pair was a bold white style with red stars and fringed tassels by Stella McCartney.
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Keeping her outfit monochromatic, Penelope hit the airport with her mom last February wearing another pair of star shoes, this time with blue flames and red lightning bolts.
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Out with the family — including brothers Mason and Reign — in New York City last September, Penelope put on a white dress with brown boots featuring bold pink stitching. This pair seems to be her favorite.
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During the same trip, Penelope broke out the brown boots once again.
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Celebrating mom turning 39 last year, P wore a comfy T-shirt and sweatpants with a pair of red cowboy boots.
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Looking overjoyed, Disick paired a rainbow shrug and a red dress with her trusty shoes.
Instagram, Kourtney Kardashian
Getting bolder, Penelope teamed her Gucci dress with bright pink cowboy boots while lounging on a matching bed.
Instagram, Scott Disick
For dinner with aunt Kim in NYC in September, Penelope kept comfy in her favorite kicks while cousin North went for maximum impact in a neon orange dress and matching eyeliner.
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Penelope’s look has traveled from New York City to Bali, where she posed with a flower in her hair and a Louis Vuitton purse.
Instagram, Kourtney Kardashian
Disick even toted her red boots all the way to Italy for a family vacation.
Instagram, Kourtney Kardashian
For brother Reign and cousin Saint West’s joint Tarzan-themed birthday party, Penelope wore a leopard-print dress with her brown pair, accessorizing with a Rolex watch and a rhinestone necklace bearing her name.
Instagram, Scott Disick
Playing in mom’s closet is fun, especially when everything pairs so well with your favorite boots.
Instagram, Kourtney Kardashian
Wendy Williams has gone full diva and more star snaps
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