Every Fashion Month since 2019, Jennifer Lopez has only RSVP'd "yes" to Fashion Week shows in New York and Paris. Fast forward to September 21, 2026, and the style icon finally returned to Italy on the eve of the Spring/Summer 2027 season. Lopez kicked off her street style series at a pre-Fashion Week dinner, wearing the peekaboo bra trend that hit the runway at Prada's show just hours later.
For her first Milan Fashion Week outfit since 2019—when she closed the Versace Spring 2020 show in a recreation of her iconic green jungle dress—it's only right Lopez showed a bit of skin. This office-friendly 'fit wasn't nearly as risqué as the cut-out Versace bodysuit, but because she's J.Lo, her white button-down remained undone, revealing a plunging black bralette underneath. Like the lingerie she styled in campaigns for Italian labels like Intimissimi and Dolce & Gabbana, the bra seemed to be lacy and semi-sheer. From there, the Maid In Manhattan actor shade-matched it to high-waisted, extra-long trousers, which shielded her peep-toe platform stilettos from the camera lens.
To finish her day-to-night look, Lopez accessorized with gold button earrings, a matching watch and bangles, and Dolce & Gabbana's My Sicily East-West Top-Handle Bag. Did this classic take on the east-west trend confirm she's attending Dolce & Gabbana's spring runway show? Only time will tell, but back in July, Lopez performed at the fashion house's "Alta Moda" showcase (wearing custom Dolce, of course).
For Lopez, as with Rihanna, Kim Kardashian, and Dua Lipa, peekaboo bras have evolved beyond their "trend" beginnings and into a fixture of her fashion. Not only does the A-lister regularly add lingerie to her work-ready wardrobe (usually by stacking bras beneath blazers), an almost identical bralette played peekaboo at Paris Couture Week as recently as July 2026.
In between runway shows, her stylists, Rob Zangardi and Mariel Haenn, dressed her in a Michael Kors Fall 2026 outfit, featuring an itty-bitty black bra, matching Bermuda shorts, and a statement feather short-sleeve coat. For her finishing touches, J.Lo paired her black-and-white look with Giuseppe Zanotti mules, a Chanel Flap Bag, and Tom Ford aviator sunglasses.
Lopez picked the perfect trend to announce her arrival at Milan Fashion Week. On Day 1, when models weren't walking the Prada runway in bras-turned-tops, lingerie emerged from beneath windbreakers, plaid shirtdresses, and trench coats.
To follow J.Lo's lead (and Prada's), shop the similar button-downs, trousers, and bras, below.
Shop Button-Downs, Trousers, and Bras Inspired by Jennifer Lopez
