Not Classic Ballet Flats, Not Loafers—Everyone With Cool Style Will Be Wearing These Shoes With Black Trousers in Fall 2025

I love dresses and skirts, but more often than not, I reach for pants. Usually, I wear jeans—both stovepipe and baggy styles—but when I want something more elevated, black trousers are my go-to. I typically pair them with ankle-length sock boots, soft leather loafers, and flip-flops. While all of these styles look chic with my bottoms, I've been searching for a new shoe pairing that's current, sophisticated, and perfect for fall 2025. Yesterday, I finally found my style inspiration in Katie Holmes's outfit.

While walking around NYC this week, Holmes wore a mid-length trench coat, a white button-down shirt, a pendant necklace, and black drawstring-waist trousers. In her hand, she held ALO's new Voyage Duffle, which launched today. This oversize bag was designed in L.A. by the ALO design house and handcrafted in Florence, Italy, by artisans with generations of experience making fine leather goods. Yes, the new duffle bag made her outfit appear expensive and fresh, but so did what she wore on her feet—square-toe ballet flats. As we all know, classic ballet flats with a rounded toe and vamp bow are a timeless and elegant option, but a square-toe design is what really elevates a simple outfit.

On Katie Holmes: Hunting Season Tagua Pendant ($275)

The next time you put on black pants and want to look luxe, throw on square-toe ballet flats—thank me or Holmes later. Keep scrolling to shop my favorite pairs.

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