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No ’90s supermodel’s wardrobe was complete without a pair of the classic 501 jeans. Cindy Crawford’s sophisticated airport outfits are all the styling inspiration you’ll need to create your own look.
Sadly, Carolyn Bessette Kennedy’s favorite Levi’s fit—the 517—isn’t currently in production. But these cropped 501s have a similar look to pairs she wore with strappy sandals and simple knit tops during the summer.
If you’re craving shorts weather, a pair of mid-thigh cutoffs can help you ease into it early. Take a cue from Jennifer Aniston, who styled hers with a navy V-neck sweater layered over a white T-shirt—a smart combination for unpredictable temperatures.
Levi’s 94 Baggy Jeans were specifically designed to mimic the slouchy fits worn throughout the decade by style icons like Janet Jackson. This easy look from the 1992 IFP/West Independent Spirit Awards is one I reference often when getting dressed in a hurry.
If you want to channel ’90s bombshells like Pamela Anderson this summer, you’ll need a pair of cut-off Levi’s shorts in your arsenal. These faded 501s are virtually identical to those of her Baywatch era.
Princess Diana preferred relaxed, high-rise fits. To recreate this look from 1997, pair these full-length, straight-leg Ribcage Jeans with this white Levi’s button-down shirt that’s half off during the Big Spring Sale.
When prices are this good, it’s worth shopping ahead for summer. This high-rise fit has a slightly longer inseam, so you can wear it baggy or flip up the hems like Halle Berry.
Black baggy jeans were a staple of the ’90s grunge movement. This spring, borrow a page from Drew Barrymore’s playbook by styling yours with a white cardigan.
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