Here's How to Actually Style Overalls Like a Grownup
Once you discover their potential, you'll reach for them repeatedly.
These days, the fashion crowd can’t seem to get enough of retro styles from every decade—like ’90s jelly sandals, '50s-era ladylike capri pants a la Audrey Hepburn, and even 80s-inspired jewelry that champions opulence to the fullest. Another throwback high on the list of favorites is the dependable overalls trend, which has gained major traction amongst the fashion set over the past few months.
It might seem like the resurgence of overalls was abrupt—and suddenly everywhere—but creator and self-proclaimed overalls lover Hailey Drew Polk will tell you otherwise. Having never truly gone out of style, Polk says, “I’ve been building my collection of overalls since high school. Nowadays, I have enough pairs to last me a lifetime.”
Although she wears overalls year-round (even paired with a bikini when temperatures peak in the summer), she loves nothing more than styling them for the fall season. “Overalls are perfect for this time of year because they can layer well over any fall essential, whether you choose to dress them up or down,” she says. “You can take a chic approach with a frilly sweater and kitten heels or keep things casual with a simple top and a pair of sneakers.”
Look toward the stylish celebrity set for more proof that overalls can swing high and low. Not too long ago, Hailey Bieber slipped into a pair of denim overalls with a $2,800 Khaite coat, pointy Toteme mules, and a Saint Laurent Manhattan bag. Meanwhile, Katie Holmes was recently spotted wearing overalls with a graphic T-shirt, an undone shacket, Mary Jane ballet flats, and a slouchy Mansur Gavriel tote.
So whatever result you aim to achieve—whether relaxed or refined—overalls can work for your personal style and lifestyle. We’ve rounded up ten outfits, Polk's favorite brands, and some veteran styling tips so you can take inspiration and master the trend your way.
Keep It Cozy
It’s officially sweater weather. Celebrate the season with a cashmere pullover worn beneath black denim overalls.
“I practically live in my dark wash denim overalls—styled with a sweet sweater tied around my shoulders,” says Polk. Consider wearing a soft jumper tucked under your overalls as temperatures drop for extra warmth. Incorporate a funky pair of sneakers if you want to test-drive colorful footwear.
It’s All About Balance
When styling roomy overalls, Polk suggests leveling out your outfit with a form-fitting top.
If the weather doesn’t call for an extra layer, slip into a T-shirt for the sake of breathability. “This look is one of my go-to outfit formulas that often carries me through early fall,” Polk says. “As for the silhouette of my top, I prefer a fitted baby tee since this snug style contrasts well with the baggy shape of my oversized overalls.” Accessorize your look with an easy, breezy crossbody bag that will allow you to roam around hands-free.
Suit Up
Where corp-core meets street style.
“If you want to add a more polished touch to your overalls outfit, enhance your look with a sharp blazer,” says Polk. Experiment with a nifty styling hack and choose to wear your overalls slightly undone so that the top portion folds over below your waist. In terms of shoes, anchor your outfit with a pair of sturdy Chelsea boots that are made for walkin’.
A Twist on the Tuxedo
Dressing in head-to-toe denim should be high on your to-do list this fall.
Canadian tuxedos are all the rage these days—stars like Beyoncé, Bella Hadid, and Katie Holmes have even co-signed the look with their distinct interpretations of the trend. Although this rugged uniform requires a jean jacket and denim bottoms, why not shake things up with denim overalls and a matching coat? Finish off your look with glossy heels and a scarf-adorned handbag.
Fall’s Favorite Hue
Embrace autumn’s quintessential color palette with brown overalls.
When you think of overalls, a set crafted with indigo denim might be the first style that comes to mind. But don’t overlook a pair coated in caramel brown, which can instantly take your outfit from zero to one hundred. Launch your look to even higher heights by wearing a white high-neck top and a black billowing bomber jacket.
Simply Striking
Dare to dazzle in statement-making overalls and a dramatic top.
For those looking to lean into a more bold vibe, Polk says that pairing your overalls with a “fabulous puff sleeve blouse and a pair of heels” will do the trick. If you’re not afraid to demand even more attention, select a pair of dressy overalls (stitched with fabric covered in shimmering embellishments or sumptuous leather). Consider this your new favorite going-out outfit. You’re welcome.
Tried-and-True
Nothing says fall like wrapping a cardigan around your shoulders.
“You can’t go wrong with an oversized cardigan and overalls,” says Polk. “This fall outfit is cozy and practical, and for that reason, it will remain in style.” Try it out for yourself if you’re looking for an easygoing outfit that will take you from a day of running errands to a laid-back lunch with friends. Cover your head with a bucket hat and wrap a scarf around your neck to give this outfit a hint of personal style.
Trends Times Two
Double up on the trends by sliding into a pair of Adidas Samba sneakers.
Tackle two trends in one look by teaming your overalls with the hottest shoes of the year, Adidas Samba OG sneakers. Compliment the colorway of these classic soccer-inspired trainers by opting for a white pair of overalls and black accessories—like a trusty tote that can pack an extra layer if you need it.
Nice and Toasty
Who says comfort and style can’t co-exist? This cuddly outfit strikes the perfect balance between the two.
Autumn weather is defined by unpredictable temperatures. Prepare for bone-chilling wind gusts later in the season by covering your overalls with a thick coat made with warm wool fabric. Stick to the comfort agenda with cushioned sneakers that make you feel like you’re walking on clouds.
A Standout Moment
If your fall wardrobe is lacking excitement, give it a vibrant punch with a pair of striped overalls.
“There are no rules in fashion,” says Polk, who encourages you to make your own. Do just that with a daring striped pair of overalls that will amp up any look. The street style image above features a coordinating jacket, but you can easily pick a more subdued layer if you're not in a matchy-matchy mood.
Meet the Overalls Expert
Hailey Drew Polk is a fashion and lifestyle influencer with 243k followers on Instagram and over 272k followers on TikTok. Polk's engaging content ranges from outfit videos to "how to style" tutorials.
