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Consider this your sign to rethink retro denim. Shailene Woodley just stepped out in a tapered jean style that’s often overlooked — but on her, it looked unexpectedly flattering, sculpting her shape in all the right ways. Safe to say, we’re officially reconsidering the throwback silhouette.
While out in New York City on March 11, 2026, the Divergent star kept the rest of her outfit simple with a white T-shirt, oversized blazer, black loafers and a sparkly yellow shoulder bag. The jeans, however, stole the show. We haven’t tracked down her exact pair just yet, but this $40 lookalike delivers the same polished, curve-friendly fit.
Get the Lee Relaxed-Fit Tapered-Leg Jean for just $40 (Was $43) at Amazon! Please note, prices are accurate at the date of publication, March 19, 2026, but are subject to change.
The Lee Relaxed-Fit Tapered-Leg Jean delivers that same retro-inspired look with a more wearable feel. Made from a soft cotton-blend fabric, it’s comfortable yet structured, while the elastic waistband adds just the right amount of stretch. The relaxed fit through the hips and gently tapered leg create a flattering, curve-skimming shape — without feeling too stiff.
It’s also easy to work into your everyday outfit rotation. Style it with a tucked-in tee and blazer for that polished, off-duty look, or keep it casual with a lightweight knit and sneakers. It comes in deep indigo, classic black and a medium blue wash that mirrors Woodley’s pair — so you can recreate the same retro feel or switch it up depending on your vibe.
Woodley isn’t the only fan of this silhouette. With over 2,100 five-star ratings, shoppers are calling them “the best jeans” they’ve ever owned for their “flattering and comfortable” fit. One reviewer even said the “elastic waist” is a “godsend,” since it means there are “no gaps.”
Woodley just gave tapered jeans a major comeback moment — and this chic version makes it wearable. You get that same structured-yet-flattering silhouette she stepped out in, just in a more everyday form. For $40, it’s totally a trend worth revisiting.
Want the retro look in a different wash? We rounded up more of our favorite Amazon styles — keep scrolling to shop!
Shop more tapered blue jeans that we love:
- Lee Legendary High Rise Mom Jean — was $43, now $20!
- Gloria Vanderbilt Classic Tapered Amanda Jeans — was $25, now $21!
- Levi Strauss Signature Gold Classic Taper Jean — $25!
- Amazon Essentials High-Rise Straight Leg Jean — $22!
- Cicy Bell Straight Tapered Leg High Waisted Jeans — was $60, now $47!
Not your style? Explore more tapered jeans here and don’t forget to check out all of Amazon’s Daily Deals for more great finds!
