How to Style Overalls

Co-authored by Kalee Hewlett

Last Updated: October 22, 2020 References

Overalls are a versatile, fashionable addition to any wardrobe. They can be styled in many ways, from classic and chic to casual and edgy, and they are wearable in any season. Dress up the look by pairing your overalls with polished tops and cuffing the hems, or keep it casual with a flannel shirt and sneakers. However you wear them, overalls are the perfect closet staple.

Method 1

Method 1 of 3:

Dressing Up Overalls

Go for a simple, clean button-down shirt in a basic color like white. ^{[1]
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Research source} Add a pair of black pointed-toe ankle boots to finish off the outfit. The black boots and black overalls will look classy and create a lengthening effect, making you look longer and slimmer. ^{[2]
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Add an off-the-shoulder top under a pair of overalls for instant class. Choose pieces in contrasting colors, such as a light gray or blush-pink top with black overalls. The off-the-shoulder top adds classiness with a hint of sexiness. ^{[3]
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- The intersecting shapes of the off-the-shoulder top and the straps of the overalls create a fun, visually interesting effect.
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Pair an ultra-feminine piece with boxy overalls for a fun mix of styles. Wear a lace or floral-print top to contrast with the overalls' structured, utilitarian style. A form-fitting top heightens this contrast even more. ^{[4]
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- To emphasize the contrast, choose a top with soft pastel colors like blush pink, light blue, or cream.
- Pairing a form-fitting top under the overalls also helps you keep from losing your silhouette.
- For a quick, stylish outfit, wear a pink and yellow fitted floral print T-shirt under a pair of black overalls. Add a pair of white sneakers and cuff the hems of your overalls.
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Cuff the ankles of the overalls for a sleeker look. Roll up the hems of your overalls above your ankles for a more fitted, tailored effect. ^{[5]
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Research source} Pair this look with some ankle boots, heels, or sneakers.
- For example, you could wear a fitted white long-sleeve shirt, a pair of cuffed denim overalls, and some heeled, camel-colored ankle boots.
- If your pants are too long to just roll once, try double rolling the hem. Make your first fold 2 inches (5.1 cm) high, then roll again to complete the look. ^{[6]
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Choose a long, flared pair of overalls for a more classic silhouette. A long, flared leg over a pair of Chelsea boots, heels, or wedges gives your outfit a dressier effect. Look for a pair that just barely touches the ground when you wear shoes.
- Wear a light blue button-down shirt beneath a pair of flared black overalls and some black chelsea boots or strappy black heels.
- For a more personalized fit, you could select a pair that's a little too long and have them hemmed to the perfect length.
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Method 2

Method 2 of 3:

Styling a Casual Outfit

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Choose loose-fitting overalls for extra comfort. Look for overalls labeled “boyfriend style” or “relaxed fit” when shopping around, which indicates a loose, slouchy fit that still flatters your figure because it tapers at the bottom. ^{[7]
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Research source} To rock the loose fit, you can also try a pair of overalls in a size larger than you would normally buy, then cuff the bottoms for a tapered effect.
- Pair a comfy yellow long-sleeved shirt with a pair of light-wash, loose-fitting overalls and white sneakers.
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Opt for classic denim with distressed details for an effortless look. Light- or medium-wash denim creates a simple, casual style. Look for overalls with a few light rips and tears for a comfortable, worn-in effect.
- For example, you could wear a black and white striped T-shirt with a pair of distressed denim overalls and some casual slip-on shoes.
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Layer your overalls with loose tops for a casual, weekend look. Adding a plaid flannel, baseball tee, band tee, or striped T-shirt underneath your overalls makes for an effortless outfit that's perfect for casual events and running errands. ^{[8]
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Research source} Pairing 2 loose pieces creates a relaxed silhouette and will keep you comfortable.
- You could also thrown on a plaid flannel shirt as a jacket or tie it around your waist. ^{[9]
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Wear easy, minimal accessories like hats and backpack purses. Baseball caps and knit beanies pair well with overalls, adding a sporty, cool element to the outfit. For a bag, try a small leather or velvet backpack purse that's both stylish and casual. Avoid bulky, statement accessories that compete with the overalls, such as bib necklaces.
- For example, you could wear a burgundy sweater with a pair of fitted black overalls and black ankle boots. Accessorize with a cozy cream-colored beanie and a black leather backpack purse.
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Add a pair of comfortable shoes to complete the look. Pair your overalls with sneakers, low-heeled Chelsea boots, or combat boots for a relaxed look. The sneakers will work best with an athletic-casual outfit, while the Chelsea boots will add an element of stylishness and elevate the outfit a bit. The combat boots give an edgier street style effect. ^{[10]
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- For an edgier look, wear a lightweight graphic sweatshirt under a pair of distressed overalls and combat boots.
- Put on a loose red hoodie, cuffed black overalls, and white sneakers for a comfortable, athletic look. ^{[11]
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- Dress down but still look stylish with a pair of dark wash denim overalls, gray T-shirt, light gray beanie, and black chelsea boots. Tie a gray and white plaid button around your hips for an even more relaxed look.
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Method 3

Method 3 of 3:

Wearing Overalls in Any Season

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Choose a white pair of overalls for the spring. White overalls look fresh, casual, and polished. ^{[12]
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Research source} Pair them with a structured piece, such as a black leather jacket, to balance out the brightness. ^{[13]
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- You could also pair them with a simple top, such as a fitted grey sweater or a color-blocked T-shirt, to make the white overalls the statement piece.
- For shoes, you could choose a casual pair of Converse high-tops, gray men's dress boots, or dressier sandals.
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Wear your overalls with a crop top to keep you cool in the summer. Showing a bit of skin with a crop top is a great option for summer. It also gives your outfit a bit of a retro feel. ^{[14]
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- To stay extra cool in the heat, opt for a pair of short overalls with your crop top.
- Keep in mind that this look is definitely more casual and generally not work-appropriate.
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Pair overalls with a chunky sweater for an autumn-inspired look. When the weather starts to get colder, just pair your overalls with a heavier top, such as a chunky, thick knit sweater or turtleneck. Choose pieces in warm, autumnal colors like forest green, rust, and mustard yellow. ^{[15]
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- Add a scarf and beanie if the weather is extra chilly.
- For footwear, choose something that will provide more coverage and warmth, such as ankle boots or a pair of leather slip-ons.
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Opt for thick denim in the colder months. Generally, you'll find thicker, more durable denim from high-quality brands. The weight of medium-to-heavy denims range between 13 to 16 ounces (370 to 450 g). ^{[16]
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Research source} Although the price may be higher than the average pair, consider it an investment. Quality denim will protect you from the chill and let you get more use out of the overalls.
- Layer a thick turtleneck under heavy denim overalls and top off your look with a printed beanie.
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How do you style short overalls?

Kalee Hewlett
Image Consultant
Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’

Kalee Hewlett

Image Consultant

Expert Answer

I'd just throw on a white T for a classic, cool look. You can also wear a basic striped shirt for something a little more textured. You don't need to do a lot with overalls; they're enough of a statement on their own that you don't want to overdo it.

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Although you can dress up overalls with tops, shoes, and accessories, remember that some occasions still may not be appropriate for overalls. For example, you may not want to wear them in conservative office settings or fancy events.

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How to Style Overalls

Steps

Dressing Up Overalls

Styling a Casual Outfit

Wearing Overalls in Any Season

Expert Q&A

Tips

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