Shailene Woodley Owns Milan Fashion Week in Lush Leather Loafers and Sculptural Tan Pumps

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Shailene Woodley owned Milan Fashion Week for the past few days, showing out in major footwear moments.

Spotted while in the fashion capital today, the “Divergent” star sported a pair of classic black leather loafers. Preppy and comfy, the star’s footwear pick featured slightly worn leather uppers accompanied by short stacked block heels and almond-shaped toes. Unlike oxfords, loafers are often less formal, thanks to their lack of laces. Keeping casual, Woodley wore a fitted plaid blazer, baseball cap and baggy denim jeans.

Shailene Woodley, loafers, leather, Milan Fashion Week, denim blazer
Shailene Woodley is seen during Milan Fashion Week on Sept. 18, 2024, in Milan.
Shailene Woodley, loafers, leather, Milan Fashion Week, denim blazer
A closer look at Shailene Woodley’s shoes.

The slip-on style is beloved by both men and women alike, making for a versatile addition to any wardrobe. A myriad of top brands carry unisex loafer styles in both black and brown leather. Woodley is one of many celebrities who love loafers. Kendall Jenner, Hailey Bieber, Katie Holmes and Bella Hadid have all been seen wearing the leather-laden style for both formal and casual occasions.

Shailene Woodley, pumps, Fendi, leather, Milan Fashion Week, monogram
Shailene Woodley at Fendi spring 2025 as part of Milan Ready to Wear Fashion Week on Sept. 17, 2024, in Milan.

The day prior, at Fendi’s spring 2025 show, the “To Catch a Killer” star sported a pair of Fendi slingback pumps in a tan sculptural style. Thin straps gave way to pointed toes a geometric heels standing at around 3 to 4 inches in height. Slinky and chic, Woodley also wore a form-fitted taupe short-sleeved maxi dress paired with an embossed monogrammed leather Fendi bowling bag.

Shailene Woodley, pumps, Fendi, leather, Milan Fashion Week, monogram
A closer look at Shailene Woodley’s shoes.

For footwear, Woodley often opts for pointed-toe pumps and stiletto-heeled sandals on the red carpet that coordinate with her ensembles hailing from top brands including Christian Louboutin, Jimmy Choo, Stuart Weitzman and Le Silla. When off-duty, her footwear features a decidedly more casual appearance, consisting of Nike sneakers and lace-up combat boots.

Fashion-wise, the star has been spotted at numerous runway shows for brands including Carolina Herrera, Dior and Louis Vuitton, as well as attending the Met Gala with Ralph Lauren, Rodarte and Christopher Kane over the years.

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Shailene Woodley at the Art of Elysium gala in Los Angeles in 2018. photo credits: MEGA
Shailene Woodley at the Art of Elysium gala in Los Angeles in 2018. photo credits: MEGA

Shailene Woodley’s Red Carpet Style Through the Years

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Launch Gallery: Shailene Woodley's Red Carpet Style Through the Years

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