In my nearly 40 years on this great earth, I have never (and I do mean never) felt more fashionable than I did in my embroidered Winnie the Pooh overalls. While your average ’90s tweens were taking their style cues from YM and Seventeen, I would pour over the Disney catalog, marking the oversized Pocahontas sleep tees and graphic Mickey sweatshirts. But the ones that filled me with outrageous confidence were those salmon-colored coveralls from page nine. They were loose in all the right places, had ample pocket room for POGs, and an ever-flattering drop crotch that made me feel dainty even though I was an 11-year-old on Weight Watchers. I’ve been chasing that sartorial high ever since.

Here I am, pictured proudly with my neighbor.

While overalls have certainly never gone away, the wardrobe staple has been more readily available at mass-market retailers lately. Take this cute pair of shortalls I just found at Old Navy. Obviously not as chic without the honey pot, but beyond comfortable.

Old Navy Slouchy Jean CutOff Overalls

Original image by Glamour Commerce Director Brie Schwartz

Original image by Glamour Commerce Director Brie Schwartz

Old Navy Slouchy Jean Cut-Off Overalls

They can be also be found in slimmer silhouettes and fabrics well beyond denim. I lived in this breathable cotton Faherty pair last summer (bonus: they’re on sale), though you can see from the second picture that they looked better on my pal Joey.

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Original image by Glamour Commerce Director Brie Schwartz

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Original image by Glamour Commerce Director Brie Schwartz

Faherty Topsail Straight Leg Overall

You can’t go wrong with the classic baggy and straight legs (some faves below). Style them simply with your go-to T-shirt (you can wear them with a fitted or looser tee–anything goes, and if you’re aiming for a ’90s vibe, opt for a trendy cropped top or a baby tee). As for shoes, this season’s trendiest footwear is all in play: jelly or fisherman sandals, or celeb-approved sneakers will all look cute.

Best Straight-Leg Overalls

Free People We The Free Ziggy Denim Overalls

Abercrombie & Fitch Overalls

Old Navy Slouchy Straight Jean Overalls

And of course, for summer, shortalls are a great choice. Pop on your favorite tank or a long-sleeve T-shirt with nautical stripes for a fresh look, and you’ve got yourself a great way to avoid thigh chafing.

Best Shortalls

Billabong Wild Pursuit Short Overalls

Free People We The Free Ziggy Shortalls

Levi’s Women’s Vintage Shortalls

Old Navy Slouchy Jean Cut-Off Overalls

Wide-leg jeans (and pants, in general) are so very of the moment. The trend extends itself nicely to an elevated overall. They can still be just as comfy and functional, but with a more fashionable spin. Just add a pair of mesh ballet flats.

Best Wide-Leg Overalls

WeWoreWhat Wide Leg Denim Overall

Luvamia Wide-leg Denim Overalls

Old Navy Baggy Wide-Leg Jean Overalls

Cicy Bell Cargo Denim Overalls

And finally, it wouldn’t be a style post in 2024 without an acknowledgment of the highly popular (and a little bit controversial) barrel-leg jeans, which are featured here in a highly wearable overall. Plus, I love the button-down jumpsuit below, which is more brunchwear than workwear.

Best Trendy Overalls

Pilcro Painter Denim Overalls

Free People We The Free Jude One-Piece

Free People Sunrays Denim Halter Jumpsuit

Free People We The Free Good Luck Barrel Overalls

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