This Once Outdated Pant Trend Is The Ultimate Transitional Staple For Fall 2025

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During a time when big and baggy silhouettes are in style, it's easy to feel like we've stepped into a time machine. Now, along with capris, another outdated pant trend from the early aughts has made a comeback: cropped flares. Perfect for transitioning from summer into the fall months, the 2000s-style trouser has been seen on fashionistas like Bella Hadid and Alexa Chung. The current fit, however, stands apart from its earlier Y2K versions. "The cropped flares from the early 2000s were a little different than they are now. Think low-rise, super tight, and usually paired with micro tops, platform flip-flops, or a pointy heel," Personal stylist and image consultant, Cynthia Kennedy, exclusively tells WOMEN. She adds, "Today's version is much more comfortable and wearable because of the higher rise, the way the fabric structure drapes, and how the silhouette feels more elevated and intentional."

After you've ditched your jean shorts this summer, it still may be too warm for full-length pants, which makes kick flares ideal for weather with a hint of chill in the air. "When the weather is still warm out, they show just enough ankle to keep things feeling cool and light. And when fall comes around, they pair just as beautifully with boots or socks," Kennedy points out. Cropped flares are also super versatile, and they don't just look awesome with a pair of sneakers. Have fun styling them with a variety of shoes and tops, and we guarantee your pair will be a fall staple in your closet.

Cropped flares can be a bit tricky to style, but as long as you get the hemline at just the right length, they'll go with any shoe you have. Sandals with kick pants are great for warm weather months, but you'll want to pair them with ankle boots for the fall. "A block heel or slim sock bootie that hits just above the hem gives you a clean, seamless, elongated line (and keeps you warm)," stylist Cynthia Kennedy exclusively shares with WOMEN. This Toms pair comes in a gorgeous maple shade that's just perfect for autumn.

As for your tops, Kennedy suggests layering oversized knits. "Wearing a slouchy, relaxed blazer, chunky sweater, or cropped jacket on top balances the fitted waist and kick flare bottom, which gives you a cozy fall vibe," the Your Style Transformation Academy creator says. And, ditch the outdated polka dot trend for fall 2025. Instead, go for solids, like this Women's Lightweight Cardigan from Amazon Essentials. "Pick pieces in the same color family (think camel flares with a butterscotch sweater), which adds an intentional, pulled-together vibe that feels chic and fresh for fall," Kennedy tells us. The stylist's last bit of advice? Play with different textures. "Go for flares in fabrics like twill, corduroy, soft wool blends, or coated denim for a fall-forward feel that instantly elevates and polishes," the expert suggests.