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.
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.
Get the Look
Zw Collection
Midi Trench
I've been buying Zara's trench coats for many seasons now. They're affordable, durable, and chic.
Banana Republic
Mid-Rise Wide-Leg Wool-Blend Drawstring Pants
J.Crew
Quinn Square-Toe Ballet Flats
Holmes's new favorite bag can take you from the office to the airport.
Shop More Black Trousers and Square-Toe Ballet Flats
Open Edit
The Curator Trousers
These look and feel like designer trousers but are half the price.
SARTO by Franco Sarto
Amaya Flexa Flats
Celebrities like Hailey Bieber, Jennifer Lawrence, and Dakota Johnson always come back to Leset for its flattering and high-quality pants.
I own these in black and wore them to the ground last fall. This year, I'll be adding the rich chocolate-brown pair to my wardrobe.
These have an elastic band in the back, lending a comfortable fit.
Mansur Gavriel
Square Toe Ballet Flats
In case you haven't heard, suede flats will be everywhere in fall 2025.
