How to Wear Overall Shorts

Co-authored by Kalee Hewlett

Last Updated: January 14, 2021 References

Comfortable and relaxed, overall shorts provide an easy all-in-one outfit, and there are many ways to style them to your preferences. Wear them casually with tees and sneakers, or dress them up with dramatic accessories and dark colors. Whatever the occasion, you can learn to wear overall shorts in fun and flattering ways.

Method 1

Method 1 of 3:

Dressing Down Overall Shorts

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Opt for light-colored denim shorts to keep the outfit simple. Light denim washes offer a classic appearance and look great during the day without seeming overdressed. When in doubt, don't overcomplicate the ensemble. Denim always has a place in everyday fashion.
- Try distressed denim shorts. The carefully placed rips and shreds turn a classic look into something a bit more edgy.
2
Choose a loose-fitting pair of overall shorts for maximum comfort. The relaxed fit creates an effortless, easy-to-wear look. Seek items labeled “relaxed” or find a pair that's a size or two larger than your usual. You'll play up the comfy casual look.
- To commit to the oversized look, wear shirts with baggy sleeves underneath or try flowy outerwear.
- If you like the loose fit but want to show off your waist, try a patterned scarf belt to pull everything in.
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3
Style the overalls without the straps on your shoulders for a carefree air. They'll look like a unique pair of denim shorts and you can show off a tee with a logo or amusing phrase. Make use of the additional real estate and show off your personality!^{[1]
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- You can also use the straps as a built-in belt by tying them around your waist.^{[2]
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- For an easy tomboy look, wear only one strap off. You can still show off a fun tee!
4
Tie a flannel shirt around the waist for a cozy look. With a long-sleeved top, you'll have an easy belted look that defines your figure. Because it's an accessory, you don't have to use a perfectly-sized shirt. The flannel is also functional; if you get cold, you can wear it over your outfit.^{[3]
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- Find flannels in funky colors like hot pink or purple for a fresher look.
5
Wear T-shirts or tank tops to keep it mellow. Classic tees epitomize casual and comfortable while still being trendy. A white tee is as timeless as it gets, but colorful shirts will brighten the entire look.
- Make sure the shirts are long enough to tuck inside the overall shorts. This will prevent shirt hems from peeking through the side of your overalls.^{[4]
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Try fun patterned tops for some pop. A relaxed outfit is the perfect time to experiment with interesting prints. Pair simple denim overall shorts with bright colors like yellow or red, or make a statement with paisley or stripes.^{[5]
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- The contrast with the denim gives an interesting mix of textures, making the whole outfit more striking.
7
Slip on low-effort shoes, like flip-flops or sneakers. Overall shorts, with all their casual coolness, are practically made for comfortable shoes like Converse.^{[6]
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Play with different accessories like hats and head wraps. The neutral but playful vibe of overall shorts allows for all kinds of accessory options. Look for pieces that enhance the chill aesthetic, but don't make you feel too fancy.
- Snapbacks, baseball caps, and beanies are great ways to accessorize. And bandanas around your head give a more easygoing look.^{[8]
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Method 2

Method 2 of 3:

Making Overall Shorts Sophisticated

1
Choose overall shorts in dark denim washes. The darker palette suits evening looks and makes a casual piece appear more mature. The color change will dress things up almost instantly.
- Try adding turtlenecks in dark shades. They're fashionable yet simple to style.^{[9]
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2
Look for belted overall shorts to define your figure. The built-in belt can cinch your waist, adding that fitted factor that makes any clothing piece seem dressy. This is especially true if paired with a smart top, like a collared shirt or a turtleneck. Opt for a cotton or linen material over denim.^{[10]
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Plan an all-black ensemble to achieve a suave image. In general, dark colors make most outfits seem more put-together. Wearing black from head to toe creates a sleek presentation. It's also an easy way to quickly decide on an outfit; all the pieces work together.
- If black seems too dreary, try wearing all-white for a chic and clean appearance.^{[11]
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4
Don a button-down shirt to add some class. Buttoned tops can create a fitted silhouette and polished appearance. Long sleeves are particularly elegant. Stick to neutral or dark colors like white or burgundy.^{[12]
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- Collared shirts will infuse your overall shorts with a touch of preppy style.^{[13]
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Try blouses in pastels or floral patterns for a sweet look. If you'd like to soften the laid back feel of your overall shorts, blouses offer femininity accented with color and charm. Adding a semi-sheer blouse under denim builds a fascinating visual effect!
- If you're not into patterns or pastels, even changing up the shirt texture can dress up the look. Try silk blouses or well-made knits.^{[14]
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- Wear an off the shoulder blouse for a flirty style.^{[15]
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Throw on a blazer for a sharp, preppy outfit. Fitted clothes make every outfit look tailored, upping the swankiness of the ensemble. Find a jacket or blazer that isn't oversized and fits your proportions comfortably.
- Make sure the sleeves stop at your wrists, and that the elbows aren't too tight when you bend.
- A cardigan also works if you prefer a piece with less structure.
7
Add a high heeled shoe for a powerful appearance. High heels dress up the overall shorts with their mature silhouette and height while showing off your legs. Ankle boots will do the same, but they take the look from refined to modern.
- Knee or thigh high boots are unexpected choices that will draw attention with their boldness.
- Try wedges if you're not into regular high heels. They'll give you height, but they're not as intimidating as heels might be, and they'll be easier to walk in.
8
Choose stately accessories to elevate the outfit. Sometimes, the accessories make the look. Level up your overall shorts with statement pieces like jeweled necklaces and stacks of metal-toned bracelets. Or try a large floppy hat for a relaxed feel that's still stylish.^{[16]
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- Throw on an ankle bracelet for a little extra bling.
- If you're not into jewelry, add dark tights under the shorts. They'll play up the fancy vibe and highlight your bottom half.

Method 3

Method 3 of 3:

Choosing Flattering Overall Shorts

1
Wear overall shorts that complement your figure. One way to narrow the clothing pool is by using your body shape as a guide. Hourglass figures will benefit from belted shorts that accentuate their waist and work with their curves. Meanwhile, athletic body types can go for bermuda short-styled bottoms to highlight their lean form.
- Record your measurements with measuring tape, then input those numbers in a body type calculator.^{[17]
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- If you're unable to measure yourself, use a body shape chart to eyeball where you might fit.
2
Focus on the length of the shorts for the best fit. Depending on your height, the hems will fall in different places, playing with your proportions. Consider how you'd like your shorts to alter or enhance your appearance. If you're not sure what looks good on you, start with shorts sporting inseams between 7 and 8 inches (18 and 20 cm).^{[18]
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- If you're petite, aim for shorter inseams relative to your height. The shorts will make your legs look much longer.
- People with long legs might cuff the hem of their shorts to balance their proportions.
- Curvier people can look for legs with a tighter fit to highlight their form.
- If you already own a pair of shorts that fit well, use the inseam to guide your search for the right overall shorts.
3
Choose the overall shorts you feel most comfortable wearing. Knowing the right length and fit for your body can help you find shorts that suit you. But if you fall in love with a piece that doesn't follow all the guidelines for best fit, wear it! Your fondness for the outfit and how you feel wearing it are the deciding factors about what clothes work best for you.

Expert Q&A

Question

What shirts look good with overall shorts?

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

Overalls look great teamed with a classic white tee. Try rolling up the sleeves for a more retro and relaxed look. Another great way to wear them is with a nautical stripe tee worn underneath. For cooler months, try teaming them with a classic long sleeve top with a clean, round neckline.