What to Wear With a Summer Maxi Skirt, Per an Editor

It’s no secret that maxi skirts are reigning supreme this summer. The long, effortless silhouette is breezy and refreshing, posing a serious threat for stiff denim and (sometimes too elevated) dresses. And with notable names like Kate Middleton, Charlize Theron, Kris Jenner, and Katie Holmes giving the style their stamp of approval, you have no real reason to leave it to the wayside. 

That said, I’ve been obsessed with the Little Moon Damasque Skirt from Aritzia, falling in love with the draped fabric, crinkle details, and comfortable elastic waistband. But for a second there, I was left asking, “What do I wear this with?” I tried on half my closet so you don’t have to—here’s exactly what to wear with a maxi skirt once you snag one (or four) of your own.   

4 Editor-Approved Maxi Skirts for Summer

It-Girl Denim Vests

Reformation Luisa Stretch Denim Vest

I instantly gravitated towards Americana denim vests, fangirling over the tailored and structured elements it brings to a rather fluid ensemble. It grounds the flirty skirt, making the look appear effortlessly cool. 

My exact pick was from Silver Jeans, though lookalike versions from Anthropologie are just as good. For something more chic, consider a scoopneck variation or sexy halterneck.         

Western Cowboy Boots

Free People Brayden Western Boots

Aside from the fact that this city girl loves country music, Western boots introduce some edge to the romantic separate. This contrast adds style tension, making your uniform look intentional. The boho vibes are also seasonless, letting you own the maxi skirt scene well into fall.  

Add a pop of color with Free People’s Brayden boots or stick to the basics with a crisp white pair from Dingo. Knee-high boots (think Ariat’s Casanovas) are another go-to for a reason; they look just as hot with shorts as they do under your long skirt.

Ruched Bodycon Tanks

Aritzia Casual Contour Flourish Top

Create a flattering silhouette with the help of a ruched bodycon tank. Instead of an oversized tee, a fitted top creates balance and keeps your figure from getting lost in a sea of fabric. They’re also easy yet polished, transitioning between occasions without the hassle of a complete wardrobe swap.

I snagged the Aritiza Contour Top the same day I bagged the skirt, fully aware it’d be my summer uniform. For a similar (more affordable option), consider the $18 Banana Republic boatneck blouse.   

Decorated Mesh Flats

Coach Emilia Mary Janes

I’m all about comfort—but I’ll never sacrifice style for ease. That’s why decorated mesh flats were an obvious choice. The airy material keeps my feet dry and fresh, while sparkles, trimmings, and embroidery add personality to a look that’s just about everywhere.  

If you do a lot of walking, scoop up the Coach Mary Janes, which include a convenient strap that holds the shoes firmly in place. For something more cutting-edge, turn towards the Steve Madden Mino Glove Flats.  

Maximalist Button-Ups

Madewell Boxy Button-Up Stripe Shirt

Ever heard of the wrong shoe theory? Well, now it’s time for the wrong shirt theory. A classic button-up top is usually reserved for sleek, refined ensembles—though it adds instant luxury and head-turning allure to a casual maxi skirt.

Maximalist options take it up a notch, with bold colors and thick stripes commanding attention. It’s an easy way to try something new, while relying on a tried-and-true silhouette.  

Low-Profile Tennis Shoes

Adidas Samba OG Tennis Shoes

While classy sandals or espadrille wedges are the typical style choice for a maxi skirt, pull a fast one and slip on a pair of sporty, low-profile sneakers. This unexpected styling decision transforms the look into something modern and totally It-girl approved.

I stayed loyal to my favorite Adidas Sambas, though dare I say the Vince Mojave Trainers would inject a bolder fashion vibe. If you prefer something more traditional, then the Gola Elan Sneakers are for you.

Mix and match the above style choices, or wear them as complete outfits as pictured. The good news? Styling a maxi skirt is simpler than it seems—it’s all about choosing what feels natural and makes you feel like your best self.