2025's Biggest Skirt Trend Looks Coolest When Worn With These Shirt and Heel Trends
It's unwavering in elegance.

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.
On Tessa Thompson: Hermes Birkin Bag ($18,000); Commission S/S 26 polo shirt and leather jacket
Get the Look
Shop More Column Skirts
Shop More Polo Shirts
Shop More Modern Pumps
Kerane Marcellus is a New York-based writer. She joined the Who What Wear team in 2025 after writing for Essence Magazine and freelancing for a number of other arts and culture publications. Fashion is a form of expression that she encourages everyone to take part in. There is no right or wrong in getting dressed! When she's not writing, she's reading in the park or gallery hopping in the city.
-
Elegant Dressers Are Replacing Their Black Skirts With This Rich Color Alternative
As seen on Tessa Thompson and in Tory Burch's S/S 26 collection.
-
It's Here: The It-Girl Skirt Trend to Wear With Kitten Heels This Fall
Bonus points if you wear it in yellow.
-
My Mom Is in Her 50s and Asked Me for Fashion Advice—8 Chic Nordstrom Outfits I Put Together for Her Under $425
Outdated prints and "ugly" shoes included.
-
This Fall Skirt Trend Will Log More Hours of Wear Time Than Your Mini and Maxi Skirts Combined
Guaranteed.
-
It's Here: The Elegant Shoe Trend Fashion People Are Trading Kitten Heels For
Elizabeth Olsen is keyed in, per usual.
-
If You Live in NYC, You *Should* Know That the Chicest Way to Wear a Miniskirt and Tights in Fall Is With This Elegant Shoe Color Trend
It's not black pumps or white sneakers.
-
If Looking Parisian Is Your Goal, Style Fall's Most "Boring" Basic Like Pamela Anderson Just Did
Simple yet chic.
-
I Live in NYC—These Are the 8 Anti-Trend Fall Pieces That Always Get Me Compliments
From everyday loafers to preppy polo sweaters.