How to Wear Shorts Over 40: 10 Tips That Will Make You Feel Confident and Chic

By
Cassie Bird
Last Modified on May 6, 2025

This post may contain affiliate links.

Age is really just a number when it comes to fashion and good style. However, as we age, our preferences do tend to shift. We may opt for more coverage in our pieces, higher quality fabrics, and flattering silhouettes. If you find yourself struggling to style shorts over 40, you’re not alone! It’s a common piece of feedback that we hear – shorts tend to be either way too short or too long. And then comes the whole issue of how to style them in a way that makes us feel chic and confident. To make styling shorts this summer a little easier, I’ve rounded up 10 tips all about how to wear shorts over 40.

1. Find the inseam that works for you

bermuda shorts | t-shirt | denim jacket | necklace | sandals | tote bag

The perfect shorts outfit starts with, of course, the perfect pair of shorts. The issue at 40 arises when you’re trying to find a pair that fits your current style. Finding the right length is one of the most important factors when you’re shopping for shorts. Even if you narrow your choices down to a great style and color that you love, your hard work is thrown out the window when the inseam is too long or too short.

If you’re shopping for a pair of shorts, the first step is to find your ideal inseam. You can do this by trying on various lengths in store, or if you’re at home, measure a pair of shorts that you currently own and love. The inseam is the length of fabric stretching from the bottom hem of the shorts to the point where the two inner thigh seams meet in the middle. Then, when you’ve found your ideal inseam in inches, use that length to filter through your options and make shopping for a new pair of shorts so much easier.

For those who prefer a longer inseam, bermuda shorts are a great option. They typically have somewhere around a 12-inch inseam. Try styling them with a striped tee, a denim jacket, crossover sandals, a straw tote, and a pendant necklace for an effortless, classic summer look.

2. Look for quality fabrics

shorts | bag | tank top | shirt | sandals | earrings

If denim shorts aren’t your thing, no worries! There are plenty of other great options out there for you, and made with quality materials. For instance, linen shorts are an ideal option for summer. They’re breathable, flexible, and oftentimes more comfortable than stiff denim. Linen is the perfect lightweight fabric for your summer pieces, especially if you live in a warm climate.

Try styling your linen shorts with other light-colored pieces to stay cool this summer. On top, try a white tank top and a breezy white button-down. Then, add a pair of white leather sandals. Finish the look with a raffia tote and gold hoop earrings for a polished, chic summer outfit idea.

3. Prioritize solid shorts or minimal patterns

shorts | sweater | sandals | hat | necklace

When it comes to wearing shorts, try to stick to solid color pieces or minimal, understated patterns. These will typically look more classic and timeless than loud, bright patterns. Plus, these low-key styles are often more flattering than shorts with big patterns or vibrant shades, which will draw additional (and possibly unwanted) attention to your hips and upper thighs.

If your favorite shorts are styles that incorporate a pattern, go for small, repetitive patterns like vertical stripes or gingham. These are still relatively neutral and never go out of style. On top, stick with a solid-colored sweater. Then, add a straw hat, suede sandals, and gold pendant earrings to introduce new textures to your outfit.

4. Balance out your proportions

shorts | shirt | flats | bag | earrings

Try to think about balancing your proportions when you choose what shorts to wear. This applies to both the proportions of your outfit as well as those of your natural body shape.

For instance, I have short legs and a long torso. To balance my proportions, I tend to gravitate toward high-waisted shorts, which will give the appearance of longer legs. If you have long legs but a short torso, you might do the exact opposite and lean toward styles that are mid to low-waisted.

As for the proportions of your outfit, use the same style principles. If you have a more voluminous top, like this white blouse, you can create the illusion of balance with a pair of a-line shorts. These will fit snugly at your waist and gently flare out around your thighs. This will give you an hourglass shape and a flattering look.

5. Stick to mostly neutral shades

shorts | blazer | t-shirt | flats | bag | earrings

One of the easiest style tips to consider when it comes to shorts over 40 is to choose neutral colors. This is especially true if you operate by a capsule wardrobe! Although it can be tempting to go for bright, bold colors in the summertime, the truth is that neutral shorts will be much easier to style. Plus, neutral colors never go out of style like other trending shades. This will ensure that you get the most wear possible out of your shorts and that they will look stylish from year to year. It will also ensure they’re easy to mix and match with your other capsule wardrobe pieces to create chic outfits all summer long.

I love white shorts for summer because they’re a bright, light shade that welcomes in warmer temperatures. Plus, they offer a great contrast to a wide range of colors. This trouser pair features flattering pleats and a high waist, which pairs well with a white tank and oversized black blazer for a sophisticated summer outfit.

6. Wear the right shoes

shorts | shirt | sweater | sneakers | sunglasses | bag

Accessories can make or break your outfit, and that principle applies to your shoes, too. Certain shoes just don’t pair well with shorts – think tall heels, chunky loafers, or thick boots. Instead, opt for lower, slimmer styles. These will help to elongate your legs, and also won’t throw your overall look off balance by adding too much visual weight to your feet.

Great examples of shoes to consider include sandals, low wedges, simple white sneakers, ballet flats, etc. You’ll find that these shoes are also much more practical for active summer days!

7. Don’t pay attention to outdated rules

chino shorts | tunic top | fisherman sandals | necklace | hat

Don’t be afraid to throw out the old rules you may have heard recited regarding what shorts are appropriate for women over 40. Fashion has no age limit! The true golden rule is to wear what you feel comfortable in – and that goes for women of any age. If you feel great in a pair of short shorts, you’ll rock them. Comfort is key when it comes to shorts – the length of your shorts shouldn’t be determined by the age on your driver’s license.

If you want to style a pair of shorter shorts, try to create balance in your look with a slightly longer top. This tunic style is great for a hot summer day. Then, accessorize with a straw hat, a pendant necklace, and fisherman sandals to complete your look.

8. Go for an a-line silhouette

vest top | shorts | sandals | bucket tote | watch | belt

I mentioned this style earlier in the post, but it’s worth bringing up again. This is one of my personal favorites when it comes to shorts style! The a-line short is flattering, comfortable, and easy to wear. It gets its name from the letter A itself. The shorts are smaller around the waistline and then flare out around the thigh area. If you prefer a little extra room around your thighs, this will be a great style for you. They’re especially flattering for those with an hourglass shape, or someone who is looking to create an hourglass shape! Add a belt for extra emphasis to highlight your natural curves.

As for the rest of your look, you can elevate the look of your denim shorts with a black vest top. Then, accessorize with strappy sandals from Gap Factory, a leather bucket tote, and a chic bracelet watch.

9. Get comfy with pull-on shorts

shorts | shirt | sweater | shoes | bag | sunglasses

If you value comfort above all else when it comes to shorts over 40, you’ll want to consider a pair of pull-on shorts. Many of these styles come in breathable fabrics like poplin, cotton, or linen. They’ll help you keep cool, and also feel like pajamas (but look much more elevated). These are one of my favorite summer staple pieces, and are perfect for a busy summer day spent with kids, walking the dog, or browsing the local farmer’s market. Plus, these styles are often very budget-friendly, and some even have pockets!

Try styling them with a chambray shirt and a sweater tied over your shoulders. Then, accessorize with East Coast aesthetic pieces like a woven bag and leather boat shoes. Complete your look with a chic pair of sunglasses.

10. Try culottes if you prefer more coverage

culottes | tank top | ballet flats | earrings | bag

Last, but not least, we have the perfect style that hovers between a typical pair of shorts and pants. Shorter than capris but longer than bermudas, culottes are a popular choice if you prefer more coverage in the summer but still like the feel of shorts. Although you never have to worry about covering up any perceived imperfections (we all have them, after all, and they’re just a part of us), you may just feel more comfortable in longer shorts or a longer length for additional sun protection or modesty.

Style culottes like a French girl by pairing them with a striped tank top, red ballet flats, a straw bag, and gold stud earrings. It’s the perfect look for a chic lunch date with friends.

The Short Answer

If you want style advice about how to wear shorts over 40, the short answer is this: wear what makes you feel comfortable! There’s no one particular tip or style that should be a hard and fast rule, but the 10 tips above might give you some guidance to find your dream pair that not only makes you feel chic and stylish, but also like your sophisticated self.

Looking for more summer outfit inspiration? Up Next: Don’t Sweat Your Style: How to Look Put Together in Hot Weather Over 50

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