Jennifer Lopez arrived at Milan Fashion Week in a black-and-white look that took classic tailoring into far more daring territory. The singer and actor was photographed in Milan wearing an oversized white button-down shirt styled open through the front, revealing a black bra underneath. She paired the shirt with high-waisted black palazzo trousers, towering platform heels and a structured black Dolce & Gabbana handbag.
It was a deceptively simple formula. White shirt. Black trousers. Black accessories. But Lopez's styling transformed familiar wardrobe staples into a polished, lingerie-revealing fashion moment perfectly timed for one of the industry's biggest weeks.
© BACKGRIDLopez's arrival comes as Milan Fashion Week Spring/Summer 2027 officially gets underway. The event runs from September 22 through September 28, with 54 physical shows on the calendar, according to Vogue. Prada opened the runway schedule on September 22, while Dolce & Gabbana is scheduled to present its collection later in the week.
Jennifer Lopez's Milan Fashion Week outfit puts a sexy spin on tailoring
The centerpiece of Jennifer Lopez's Milan Fashion Week outfit was her crisp white shirt. Rather than wearing the button-down fully fastened, Lopez left several buttons undone, exposing a black bra underneath. The shirt's slightly oversized proportions and rolled sleeves gave the otherwise tailored piece a more relaxed quality.
© BACKGRIDLopez's look was built around two classic pieces, a white shirt and black dress trousers. The styling plays with the contrast between traditional officewear and lingerie dressing. Instead of abandoning tailoring for something overtly evening-focused, Lopez essentially loosened the rules of a familiar workwear combination.
© BACKGRIDThat contrast is especially effective because the individual pieces remain understated. There are no loud prints competing for attention, and the monochromatic palette keeps the outfit cohesive.
Her high-waisted palazzo trousers create an extra-long silhouette
Lopez balanced the volume of her shirt with high-waisted black palazzo trousers. The pants sit high at the waist before falling into dramatically wide, long legs. Their length nearly conceals her shoes, creating an uninterrupted vertical line from waist to floor.
© BACKGRIDUnderneath, Lopez appears to be wearing high black platform heels, adding even more height to the elongated silhouette.
The day before, JLo rocked a sharply tailored pinstripe blazer and shimmering floral skirt while heading to a meeting with her longtime manager, Benny Medina, on September 20. Rather than reaching for a conventional pantsuit, she chose a runway ensemble from Valentino’s Pre-Fall 2026 Ready-to-Wear collection. It was corporate dressing, but the J.Lo’s way.
© BACKGRIDThe aesthetic borrows recognizable office staples, including blazers, tailoring, button-downs and polished shoes, but the star rarely wears them in traditional ways.
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