2025's Biggest Skirt Trend Looks Coolest When Worn With These Shirt and Heel Trends

By Swedan MargenOctober 23, 2025

It’s official: Celebrities are endorsing the skirt trend of the year, on the heels of it making appearances on the Gucci and Max Mara (among others) runways of the F/W 25 season. It’s a minimalist-adored ‘90s trend that's found its way back into fashion people’s hearts: the column skirt. The straight-all-the-way-down silhouette was recently sported by none other than Tessa Thompson while heading to a talk show appearance in NYC this week. Given her endorsement (she's become quite the trendsetter), it's safe to say that it's one of the top It-girl items of the season.

When it comes to what to wear with a column skirt, take a cue from Thompson's styling. Her shirt and shoes, in particular, were the perfect trends to wear with the elegant skirt: a polo shirt and modern pumps. To complete the look, she added a striped leather jacket and a Birkin bag. The outfit was as cool-girl-coded as it gets. A column skirt is a smart styling choice, as you can see from Thompson’s look; the silhouette elevates an outfit instantly.

If you’re on the hunt for a way to wear the coolest trend of 2025, keep scrolling to recreate this look and shop similar items.