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Jamie Chung, ESC Boots

Ron Adar/WireImage

From October to March, chances are your feet will live in some form of bootie. Who are we kidding? Ankle boots transcend the cold-weather seasons—with music festivals and weekend jaunts being optimal times to break out the wardrobe staple.

However, any style savant knows that not all booties are created the same—different styling is required for specific shoes. For example, the lace-up kind is inherently casual but intricate in design, which makes pairing clothing with it all the more difficult. On the other hand, sleek retro iterations can veer too costume-y if worn with your everyday flares. In other words, we need help when deciphering how to wear our booties—and where better to find inspiration than the stars.

Take note from celebs like Kendell Jenner and Jamie Chung, and pair your favorite booties with these outfits.