Not Classic Ballet Flats, Not Loafers—Everyone With Cool Style Will Be Wearing These Shoes With Black Trousers This Autumn
Such a classic, failsafe outfit combo and if it's good enough for Katie Holmes, it's good enough for us.

Chloe Gallacher
I love dresses and skirts, but more often than not, I reach for trousers. Usually, I wear jeans—both straight-leg 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 trousers, I've been searching for a new shoe pairing that's current, sophisticated, and perfect for autumn 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 on 22nd September. This oversized 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. While it's only available in store and not online, we still can't get enough of it. 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.
The next time you put on black trousers and want to look luxe, throw on square-toe ballet flats—thank me or Holmes later. Keep scrolling to shop my favourite pairs.
Shop Katie Holmes' Look:
Shop More Black Trousers and Square-Toe Ballet Flats:
Nikki Chwatt is an associate fashion editor based in New York City. She joined Who What Wear in 2024 after writing fashion, beauty, and lifestyle content for WWD, Well+Good, Editorialist, and more. With a passion for personal style and the creativity that comes with it, one of Chwatt's goals is to help others understand that there is no such thing as a “good” or “bad” style; it’s just about putting an outfit together that makes you feel confident in yourself. When she's not writing, you can find her taking a Pilates class, reading a powerful romance novel, or exploring a new wellness spot in Manhattan.
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