Overalls are back on the fashion agenda for summer 2026, but not in the way you might remember them. The latest iteration of the nostalgic wardrobe staple trades twee skinny silhouettes and schoolyard styling for relaxed fits, barrel legs, crisp white denim, and accessories that feel playful without looking too young. 

Whether you've spotted them on your TikTok feed, your Pinterest page, or on a chic person walking down the street one thing is clear: overalls have officially entered their cool-girl era.

To break down exactly how to wear overalls this summer without looking like you're trying too hard, we turned to content creator, Marshalls and TJ Maxx Trend Expert, and NYC fashion darling Mandy Lee, better known as Old Loser in Brooklyn on TikTok.

Ahead, she shares the silhouettes, styling tricks, and unexpected pairings that make the summer-perfect denim pick feel fresh, effortless, and grown up.

"The key to making overalls feel stylish and fun is all in the silhouette and wash," she told E!. "I always recommend looking for a style that feels current with what’s trending and also aligned with your personal style and preferences. Overall, we’re seeing a shift towards slightly relaxed, wide-leg fits — something that feels effortless versus tight and suffocating."

"For summer, you can never go wrong with a light wash or a classic white denim," she shared. "Those shades instantly look elevated and pair beautifully with everything, from crisp basics to bold accessories."

This pair of denim overalls is made with a supersoft cotton-Tencel blend and comes in a relaxed fit. Choose from many colors.

These coastal-cool barrel leg overalls are just $50 right now and perfect for summer.

Step into these easy, effortless overalls from We The Free, featured in a soft denim fabrication with a slightly barreled leg and grommet details. Choose from three colors.

The definition of a one-and-done, this one-piece from FP's We The Free collection is the perfect instant outfit.

"One of my favorite styling tricks is to treat overalls like a statement jumpsuit. I love pairing overalls with playful accessories like a structured beaded bag, layered jewelry, and funky jelly sandals to create a fun summer look with personality," she explained.

We found a few fun bag options below that scream "summer."

The fun fruit motif on this beaded bag is so summery and fun!

Fresh stripes and ripe fruits infuse this beaded shoulder bag with effortless summer style, perfect for elevating your vacation look.

"A fitted tank is the easiest summer option because it balances the relaxed shape of the overalls," she said. "I also love a ribbed knit tank, a striped knit, or even a lightweight button-down left slightly open at the neckline. A printed or graphic t-shirt is also a fun idea – unclip one side of the overalls to reveal more of the print and strike visual interest." 

This must-have tank is made with ribbed fabric that’s a little thicker, a lot cuter. Choose from a few shades.

The This Song Reminds Me Of You T-Shirt from Lonely Ghost turns everyday style into a nostalgic moment. Featuring short sleeves, a crew neckline, and a relaxed fit, it’s finished with a This Song Reminds Me of You front graphic and a song list graphic on the back.

This adorable top is nice and stretchy! Plus, it's breathable so it's perfect for summer. 

"I personally really enjoy a mesh or jelly flat situation—especially in the summer. Footwear is always a great way to add personality to an outfit without overwhelming your overall aesthetic. Personally, I think mesh ballet flats look best when the outfit feels sleek and modern. Mesh ballet flats started making waves 3 summers ago, so it’s safe to say they have some staying power," she said.

These heeled jelly sandals really elevate any look while still keeping your feet comfortable.

This heel features a comfortable kitten heel, a chic thong strap design, and a classic square toe. Choose from many colors.

This mesh Madwell ballet flat is comfy, breathable, and easy to wear with dresses, denim, linen, and more. It features a fitted glove design and square toe, plus a cushioned footbed for added comfort.

These slip-on mesh ballet flats come in so many colors and won't give you blisters due to its airy netting design.

"Shorteralls are having a real comeback, especially while our feeds are filled with a slew of playful and nostalgic trends," she said. "For example, styling shorteralls with a crisp oversized button-down underneath, a fitted tank, or even a swimsuit if you’re on vacation are all easy ways to make the trend feel intentional and effortless."

Perfectly baggy, these utility-inspired overalls from Levi’s are perfect for endless effortless outfitting.

We love the black shade of these loose denim shortalls. They're on sale now!

This breezy button-down can be worn under or over a pair of shorteralls. Get it on sale now. Choose from many colors!

This pretty eyelet-embroidered blouse provides a fun juxtaposition to the casualness of the overall shorts.

Looking for more summer styling inspo? Gingham Is the Whimsical Summer Style Trend Made for Fourth of July Weekend

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