Since the invention of overalls in the mid-18th century, these almost-bodysuits have gone through a tremendous number of fashion trends. Yet, the familiar design has remained, more or less, intact. Sure, at times the way you wear overalls has transitioned as well, but the premise is still the same.
In fact, I remember as a kid going through a whole season of trendy overall-wearing that consisted of leaving one buckle undone. Yes, the 90s was all about fashion. While that trend was left firmly from whence it came, overalls have continued to move forward.
When one thinks of denim overalls, the first thought that comes to mind might be that of a farmer or manual laborer. But, as fashion does, the article of clothing has been seized by the opportunity to make it into something else. To count yourself in vogue with overalls, you can add a jacket, accessories, high heels, sheer shirts over the top, and even go up a couple of sizes for an extra roomy appearance.
FYI, thanks to AI imagery software, we’re able to create very specific fashion and hairstyle examples to illustrate the points being made. In some cases, imagery is exaggerated to hammer home the point.
A History of Overalls
As mentioned, overalls first came into existence almost 300 years ago from the British army. The purpose of the clothing is still the common reason for many who wear overalls today, protection. Back then, it was to keep formal clothing clean. Later on, they were given to slaves to work in.
A century forward, Levi Stauss co-created the first pair of jeans, which were a type of overalls. The overall jeans were like high-waisted baggy pants with thick suspenders to keep them up. By the start of the 1900s, the bib part of the overall was added.
By the end of the 20s, we had a look more similar to the overalls of modern-day; the bib-and-brace. The pants and beyond look became widespread during The Great Depression as a functional garment.
The handiness stuck and soon people who weren’t working in them began wearing overalls just like normal clothing. Pretty soon, it was the cute thing to put your kids in for formal Easter pictures with pastel colors. Just ask my brother.
How to Wear Jackets with Overalls, a Style Guide
Now that we’ve established that it is acceptable, and even a statement, to wear a jacket with your overalls, what does that look like? After all, there are many kinds of jackets, just like there are a variety of overalls. To be fair, you can wear any kind of jacket with any type of overalls. The question here though is, what is the look you’re going for?
The Rocker
For this look, a pair of black overalls with a form fit. Add a light or white shirt underneath. Top that with a black leather jacket. Complete the outfit with a silver chain belt, big sunglasses, and a shiny pair of shoes to match the shiny jacket.
The Rain Man
What do you do when the weather doesn’t look super encouraging but you still want to show off your cute outfit? You wear a transparent jacket. For this look, you will want to wear overall shorts because the last thing you want to do is drag pants through mud puddles.
This jacket is not meant for all-day wear. Transparent jackets feel like smooth, flexible plastic. It’s great to look at but will make you sweaty, as it’s not meant to breathe like cotton. So, wear one for quick jots with the intention of taking it off inside of your destination.
The Professional
Overalls may remind most people of physical work, but for this look, it’s about a different type of work. Start with a dark pair that is formfitting. Match the shirt with an elongated blazer.
This way, it’s your choice to expose the overalls or not with the snap of a button. Add some heels and a crossbody bag or briefcase and you mean business.
The Shopper
Put on a black shirt underneath denim overalls for this look. You’re just going out to walk around and run some errands so you want to be comfortable yet stylish. So, we’re going to top this outfit with a long, plaid jacket and a solid-colored pair of flats.
Since you’ll be running around, add a hat. If your hair is long, pull it into a side ponytail or low bun to accommodate whatever hat you choose.
The Dresser
For this look, you’ll want to pair your favorite overalls with a maxi top. A maxi top is a sort of like a maxi dress that isn’t sewed together. So, it’s not exactly a jacket, but it offers similar support. The sleeves are long and they cover you. It might not keep you warm, but it does offer a nice pop of color or patterns.
Depending on what your maxi top looks like, it will influence the top you wear under the overalls. If it’s a pattern, put on a solid color. If it’s just splashes of color, you might want to pick a white or black top.
You can add a chunky belt to go over both the maxi top and overalls if you want to avoid the free flow of the maxi. You can also just add a tiny clip to keep the maxi top together but not be weighed down by a belt.
A Jacket and Overalls for All Seasons
So, as you may have picked up from The Rain Man, not every jacket is meant for cold weather. Sometimes, jackets are more of a testament to the outfit. These days, overalls come in varying lengths and materials just like jackets do.
You can even double down on the denim, as Marie Claire explains, “Go for the ultimate denim-on-denim look with overalls and a jacket on top. You can go with a cropped piece or opt for a long jacket that ties your outfit together from top to bottom.”
What that really means is that, if you’re an overall lover, you can wear them all year and never wear out a look. Here are my best jacket and overall pairings to last from January through December.
Winter
Baby, it’s cold outside. No matter where you live, you need extra coverage this time of year. This calls for wide-leg, Corduroy overalls with a hooded faux fur jacket.
Spring
Flowers are in bloom and so are you. Get a pair of Capri denim overalls to frolic in. To be fair, you can also use form-fitting overalls that you can roll up, Capri style. Take a light fleece jacket with you, just in case.
Summer
The sun is blazing and the last thing you may want is a jacket. However, have you been inside a movie theater? I’ll do you one better. Have you ever been inside an office building during the summer? It often seems like the hotter it is outside, the more of a polar ice cap there is inside. Anyway, bring a sheer maxi top to go with cotton overall shorts.
Autumn
While the weather is working towards being frigid again, regular denim overalls are the perfect fit. A great jacket for this time of year, with these types of pants, is a bomber jacket. Comfortable, warm, and stylish. As Who What Wear puts it, “Pile on the outerwear—whether it’s a leather jacket or a faux-fur coat.”