Without question, the sneaker trend is here to stay.  Here’s the deal…once style influencers started wearing sneakers with skirts and dresses….all bets were off.  

There are so many fun ways to style skirts and sneakers.  One of my favorite fall looks is a skirt paired with an oversized sweater and sneakers.  For fall, think about repurposing the floral midi you wore all summer….just add cute sneakers.  Know what you get when you wear a maxi skirt, sweatshirt, and high-tops?  An adorable bohemian look!

Animal print skirts paired with sneakers are super on-trend.  A Pinterest look we adore shows an animal print skirt worn three ways…with a sweater and booties…with heels and a blazer…and with a sweatshirt and sneakers.  Another favorite is a tiered leopard skirt topped with a t-shirt, jean jacket, and Chanel bag.  And the Golden Goose sneakers definitely give it that extra pop of style!


If you’ve been on the lookout for stylish sneakers, Anthropologie is the place to shop.  On top of having sneakers that go with every outfit, they share an online variety of ways to style them.  I’m loving how they combine a dainty orange tulle maxi skirt with leather high-tops.  If I were styling this outfit, my personal pick would be their Dolce Vita snake-embossed leather sneakers.  


Typically, you see pleated skirts paired with heels.  But there is no excuse these days for being uncomfortable.  So think about kicking up your work style wearing sneakers with your skirt.  A pleated skirt looks fun and flirty with an oversized sweater and business-like with a blazer.  Another way to dress-up your skirt/sneaker look is with a leather jacket.

Women in their 50s and older are also sporting the sneaker/skirt trend.  I’m loving how a “60ish” style influencer from Bochum, Germany styles a green pleated skirt with a blazer and sneakers.  And don’t you think she looks adorable in a leopard print skirt with a red and white striped sweater…and sneakers, of course?  

From travel to running errands to a professional career….the sneaker/skirt trend is definitely here to stay.  Is that a smile I see on your face?  

Holley Williams is a personal stylist specializing in closet inventory, seasonal shopping, and wardrobe consultation.  Be sure to check her Holley Williams Style on Pinterest.  Contact Holley at [email protected].