Katie Just Wore the Anti-Trend Flats That Make Maxi Skirts Look Cool (Not Dated) in 2026
Not ballet flats, not mesh flats—This is the shoe trend that looks the best with maxi skirts this spring.
It's that time of year when our jeans and trousers deserve a well-earned break. As the weather warms, the heavier fabrics and full-length cuts that served us through the cooler months suddenly feel overworn. To replace them, we should look to transitional pieces like maxi skirts, since they're easy and breathable while still keeping the legs covered. We're not the only ones on board with this idea. Katie Holmes is, too.
Recently, while strolling through NYC, Holmes was seen in a very spring-appropriate outfit. She wore a white T-shirt paired with a blue poplin maxi skirt featuring a red trim. Her look was finished with a leather shoulder bag and Gucci Jordaan loafers.
On Katie Holmes: Rosie Assoulin skirt; Gucci Jordaan Leather Loafers ($1090)
With a closet full of shoes, Holmes could have chosen any pair to style with her skirt, but her decision to pair them with the designer loafers felt intentional. The Jordaan loafers are a true wardrobe staple. They've been around since 1953 and are still highly coveted for their low profile, sleek design, and small Horsebit hardware, an if-you-know-you-know symbol that signals good taste. The flats are also incredibly versatile, often paired with classic jeans and trousers, but they work just as well with a colored skirt, grounding the look and adding a timeless touch.
Keep scrolling to shop the chicest maxi skirts and loafers to pair with them.
Shop the Best Loafers and Maxi Skirts:
Celebrities like Katy Holmes, Natalie Portman, and Dakota Johnson keep wearing Gucci loafers.

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.