Denim Overall Outfits That Don't Make You Feel Like a Toddler? Yeah, They're Possible

Almost 15 years ago, I acquired a pair of vintage Lee overalls from New York institution What Goes Around Comes Around. I am still bewildered as to what inspired the purchase for my first adult pair, and why I urgently jumped to tailor them a bit more fitted in the legs and just a touch shorter at the hem. Despite successfully making it through four different moves and countless wardrobe purges since, I never wore them. I don’t remember them being remarkably expensive or “of the moment” circa 2010, but I guess I felt they would catch on for me one day. Alas, through pregnancy, many outdoorsy summers, and even Halloweens, these sweet Lees never had their time to shine. They’ve been a lingering styling puzzle I had yet to solve—until now.

Overalls are highly specific, so I had to think about my approach carefully. Immediately I associate them with being outdoorsy, so I didn’t want my look to read, to quote Clueless, “She could be a farmer in those clothes.” I had to keep these far from the obvious accompaniments, like flannels and western boots. Even when trying a little silk scarf with them, it felt too “bandana,” and I had to separate the two. Overalls can also come across as a little juvenile, or young-adjacent. Love me some Ms. Rachel, but she’s not the style icon I wanted to channel in this process, nor was my actual toddler. I had to stay away from T-shirts or anything super fitted underneath, for fear of it looking like a onesie.

I decided on three different overall outfit scenarios: workday, night out, and weekends, to cover my bases. The dark wash of my pair could lend itself easily to professional or evening scenarios, just as well as days off. I also like their longer length, which could be worn with heels, haphazardly tucked into boots, or cuffed up and still baggy. There was a lot to play with there.

Mine are vintage and tailored to me perfectly, but when shopping for a versatile pair, the fit is important to note. They should be slim but not too tight throughout the leg. (They feel less cool when they are too snug.) For maximum comfort and ease, the crotch needs to be a little baggy. Wide legs on overalls can be a little too casual, and too big is a little too sloppy. This new Lee pair feels pretty close to mine, but I do endorse going vintage and visiting a tailor—they just feel really good and cozy, not as stiff as they would fresh out of the box.

I thought a lot about how French and Japanese street style interprets Americana, making it look even “cooler” than its stateside origins. They don’t take it at face value, and sometimes push forward with the literal in a way that feels like a bit of a caricature. Playing with proportions and unexpected pairings to exaggerate the idea of the classic staple has a great deal to do with this, but I also had to make these outfits feel approachable and functional in my low-key New England life. In other words: not too fashion or too avant-garde.

How to wear overalls to work

First up, my “office” look. As a freelancer, I rarely go to an actual office, but I often show up for work on set for a shoot or to meetings with designers, which offer me the opportunity to flex my style a bit. I know I just got off to a start, but I think this look was my favorite. I borrowed my husband’s Brooks Brothers tweed sportscoat and added a boxy turtleneck under. I popped on a pair of slouchy boots in a graphic print, added a gold pendant with my trusty watch, and brought the whole thing back down to earth a bit with a boat tote. I felt great in this, and it reminded me of an Isabel Marant-esque French girl. It was super comfortable, and felt cool and not too edgy—perfect for my coastal town or trips to New York. 10/10 will wear again, no notes.

How to wear overalls for the weekend

For my “weekend” look, I wanted to channel what I’ve seen looking through ‘80s street style magazines, and landed on my version of “sporty,” which usually runs pretty retro. I paired my overalls with a secondhand Marc Jacobs puffed-sleeve rugby under a nylon parka with a cinched waist. I added pops of color in a sweatshirt around the waist, to make the one-piece a little more form-fitting, and a weird neon shoe with a white slouchy sock for the 80’s element. Topping it off with a techy nylon backpack and cuffing the overalls showed off the shoes more and also made them bike-friendly, which is an important element for me on the weekends. The final look was easy to execute, and adding in graphic elements like stripes and pops of colors made it unusual enough to feel like I was wearing an outfit versus just throwing some clothes on for a day out and about.

How to style overalls for a night out

To round out my trio, I did a little research and noticed a lot of Japanese styling of overalls included a ruffly or billowy shirt underneath. I had a vintage one with a pretty girly collar, so I leaned more into a feminine take for this. I added a cardigan with pearl buttons, a pop of red heels, a classic bag in a timeless pattern, a crystal tennis necklace, and even a black ribbon barrette, to drive the point home. I could see this for a girls’ night or a casual date with my husband for sure. I also would like to experiment a bit more with a blouse pairing, and maybe venture out with a more flowy proportion to see where I could push it further.