The Chicest Shoe Trends to Wear With Leggings, Jeans, and Skirts

While we’re always down for surprising and statement shoe styles for special occasions, it’s those more versatile silhouettes that are of utmost interest for day-to-day life. Although, we totally understand that your footwear selection of choice these days is likely a fresh pair of tube socks to stay comfy at home with the current situation. Well, if you are interested in shoe shopping or want a bit of shoe inspiration to bookmark now and note for later, we wanted to take the next few moments to cover some of the top shoe trends of the moment.
With versatility top of mind, the three silhouettes in question are particularly noteworthy because they team flawlessly with anything, including common staples like leggings, jeans, and skirts. To highlight further, we’re showcasing past imagery of how fashion girls have worn the chicest shoe trends right now with all three of the essentials above—complete with some shopping picks on how to get each look, too.
Black Mules
While a more laid-back shoe choice might come to mind first when thinking about a legging ensemble, a sleek pair of pointed black mules elevates the pant style even more, like in this 'fit featuring the leather jacket and cool accessories.
A tube top is particularly trendy with jeans and polished mules.
Tie-up mules are forward and elevated with a printed silk skirt and a chunky knit.
Sporty Sandals
Featuring Velcro straps and sporty materials, these of-the-moment sporty sandals are an ideal match with a cool legging ensemble.
Embrace a pastel or white sandal silhouette with a pretty monochromatic look.
Adding socks to these sandals feels just right paired with a sleek leather skirt.
Retro Sneakers
Throwback sneakers are basically everywhere right now and will make anything you're wearing feel quite current. Case in point? This sweater-and-legging combo.
Wider-leg, light-wash jeans are where it's at with these retro sneakers.
Go for a full-on sporty look by taking a note from this outfit with the pleated skirt, pullover, and trusty sneakers.
Next, check out more comfortable shoe trends worth trying.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
Aritzia Is a Fashion-Person Paradise—These 25 Standouts Are Now On Major Sale
The basics alone are worth checking out.
-
These 30 Simple Yet Elevated Picks From the Nordstrom Anniversary Sale Are Giving Major Rich Vibes
Hello, instant confidence boost.
-
These 31 Classic Nordstrom Anniversary Sale Finds Are the Key to a Rich-Looking Summer Wardrobe
Imagine the chic outfits.
-
Hello, Fans of Non-Skinny Jeans—These Styles From the Nordstrom Anniversary Sale Are Perfect for Fashion People
Don't miss out on the discounts.
-
It's Now or Never—54 Last-Minute Amazon Prime Day Deals You'll Regret Skipping
Elevated basics, celeb dupes, luxe-like styles, and more on sale.
-
Just so You Know, *This* Is the Denim Trend New Yorkers Wear With Loafers (Sorry, Skinny Jeans)
And they're on sale right now on Amazon.
-
I Shop for a Living—These 30 Elevated Fashion, Beauty, and Home Décor Picks From the Amazon Prime Day Sale Have My Attention
Chic, practical, and affordable.
-
Hailey Bieber Already Wore the Denim Outfits That Will Define Fall 2025
She's always setting the trends.