Peep-Toe Heels Are Dominating in Milan in Fall 2025

We often discuss the chic street style in Paris; however, Milan is equally impressive—its sidewalks are constantly filled with some of the most stylish people, especially during fashion week, which is happening now. Celebrities and fashion insiders worldwide have come together to view collections by heritage brands such as Prada, Max Mara, and Fendi, all while displaying the most refined looks. A recurring feature in many ensembles is the peep-toe heels, worn by numerous attendees, including actress Shailene Woodley.

At Fendi’s S/S 26 show in Milan, Woodley was seen wearing a brown silk and lace slip dress, styled with a Fendi Peekaboo bag and peep-toe wedges. Although the dress would also look elegant with classic black pumps, pairing it with black wedge-heeled peep toes added an extra touch of coolness and modernity.

For those who may not know, peep-toe shoes are “in” again, as declared by the spring/summer 2025 collections, which showed in September 2024. Designers like Chloé, Miu Miu, and Tory Burch have reimagined the “dated” style with modern details, such as interesting toe or heel designs. And, brands like Zara and Reformation have taken notice, creating their own versions. With that said, keep scrolling to see Woodley’s ensemble and shop the best peep-toe heels available now.

On Shailene Woodley: Fendi Peekabo Mini Bag ($5650)

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