The best women’s shorts that fit and flatter women over 40 of any shape

Many women over 40 avoid shorts because they simply don’t know how to choose (or style) a pair in a chic and flattering way.

But shorts can be fabulous to wear in summer. This guide will tell you where to find the best women’s shorts and how women over 40 can wear them.

How to pick the best women’s shorts for women over 40

If you’re wondering how to find the best women’s shorts that would be flattering for your age and figure, let’s go over 3 things:

1.Body shape

Most women are one (or sometimes a combination) of 5 different body shapes: apple, pear, rectangle, inverted triangle and hourglass.

If you don’t know your body shape, read our article on how to find your body shape.

Certain shorts will work better on one shape over another. Keep your shape in mind when looking at the styles below.

2. Height

Height can also add to the variable of how to best shorts for your body shape.

Petite women should be more careful of how much fabric the shorts have in the form of bows, pleats and other details, which can overwhelm the frame.

Regardless of height, always consider if the shorts you’re trying on are the right length for your height. If they’re too long, hem them. Too short? Choose another pair.

3. Legs

Legs are probably the top reason most women won’t wear shorts. Being self conscious about cellulite, veins, scars or other issues are valid but there are solutions.

Choose longer short styles to hide imperfections that may make you self-conscious like cellulite.

Why not wear a pair of lightweight stocking under a shorter pair of shorts like below? It’s a fashion-forward look and some tights or stockings like the ones Spanx makes will also conceal veins or scars and smooth the body fat in your legs. Give this look a try for Spring or Fall.

What are the best women’s shorts and most flattering shorts for each body shape?

Most of you will only wear shorts for summer or for your vacations. That’s usually when I wear my shorts.

Let’s break shorts down into current styles and who they’re best for.

 Khaki women’s shorts – Best shorts for a safari holiday

khaki shorts are ideal for a safari holiday. Above is how I wore mine during my holiday in Namibia.

If you love a natural look, then khaki shorts would be a lovely option. I can definitely imagine Jennifer Aniston wearing these ones.

For more inspiration on how to dress like Jennifer Aniston, check out this article.

Caslon are a good brand to try for khaki shorts

This pair (below) are the Caslon utility shorts and they have good reviews in Nordstrom.

But, if you did want a pair which are a couple of inches longer, you could opt for the twill shorts.

Utility Shorts

High waisted shorts with a flare: the best dressy shorts to go for dinner or on evening walk

What they are: High waisted flare shorts look like a skirt because of the flared legs and fitted and defined waistline. They’re often shorter in length, around mid-thigh. This style is on trend right now and is fresh, flirty and feminine.

What woman should wear this style: It’s the perfect style for pear, apple and inverted shapes because it cinches and accentuates the waist, tucks the tummy in and flares at the leg, sort of like an A-line skirt. Although any woman of any shape would find this style flattering of they want to accentuate their waistline! Especially those looking for a pair of shorts that tend to conceal your thighs and hips by draping softly around them.

How to wear high waisted flare shorts: Get your girly game on, because this style is great with feminine accessories. A heel, wedge or dainty mule or sandal would be a great shoe option. Because of all the attention around the waist from this style, keep the top clean, minimal and tucked in. Layering with a shorter cardigan adds polish to the style.

Satin tie waist shorts

I also really like these ones.

Belted high waist shorts

I find my high waisted flare women’s shorts particularly good for more dressy occassions. Below is how I wore mine on a holiday to the Maldives during the evening for a stroll on the boulevard and outdoor dinner.

Bermuda shorts

What they are: Bermuda shorts are slightly fitted, straight up and down in cut, are longer (falling around 1 to 2″ above the knee) and can be worn rolled up or with a cuff. Many companies call any short that is mid-thigh length or longer a bermuda.

What woman should wear this style: The rectangle or hourglass shape woman would find this style flattering, because they aren’t cut for the big hips or curves of other shapes. The other body shapes should avoid them, since they could feel too tight around the hips, waist and/or butt area. Most women would then try to buy them in a bigger size and then end up with improperly fitting bermudas.

How to wear bermuda shorts: Depending on your style, bermuda shorts can be dressed up or down. They are versatile enough to be worn with a t-shirt and sandals, in which case you can roll them up, or if they have a nice fabric to them, dress them up with a blouse and wedge heels. I especially love this style with a loose, wrap cardigan, mid-size belt and slip-on flats or sneakers.

The pair below are from Not Your Daughter’s Jeans (NYDJ), which is one of my favorite jeans brands. Tighter bermuda shorts tend to be more flattering that really wide ones as wider ones can really widen you and make your look bigger than you are.

I like to wear my longer bermuda shorts in a relaxed casual way with a longer tunic. Perfect for strolling along the beach.

Bermuda shorts

Pleated shorts

What they are: A pleated short style has some type of pleat detail to the front of it. The length on this style of shorts can vary. Pleated shorts can be tricky, so the important rule of thumb is to look for a pair without too many pleats, folds or other ornamentation.

What woman should wear this style: This style can be worn by all body shapes. The pleats on the legs are roomy enough to hide imperfections or downplay larger thighs. The shape of pleated shorts is wonderful for petite or rectangle women who may want a little extra volume. The cut is more like a structured skirt. It’s the perfect shorts style for the 40+ fashionista.

How to wear pleated shorts: The secret to this style is to choose a quality fabric and the right fit. A longer, pleated short is a fun and feminine style. But fabric that is too bulky or a pleated short that is too tight or loose can be highly unflattering. For a fashion-forward, avant-garde look, choose a longer knee length style, urban colors like blacks, grays or bold tones and pair with bold accessories.

Pleated Shorts

Pants shorts

What they are: Trouser or pants shorts for women are perhaps the most flattering style of all. They’re essentially well-tailored trousers. They vary in style from very short to 1″ above the knee. They are similar to the bermuda short but dressier and often constructed in finer fabrics.

What woman should wear this style: Any woman can wear this style. Even the length is a matter of preference! It’s a myth that petite women should wear shorter shorts and taller women should wear long shorts. Go with what you like and feels right for you.

How to wear trouser shorts: The trouser short is so nicely constructed, you’ll want to tuck in your top and add a belt. This is a great dressier style that can be paired with a lightweight silk sweater or a jacket for a short pants suit.

Stretch woven trouser shorts

More types of shorts

While these are the main shapes of shorts you could opt for, there are of course lots of types of shorts within those categories that you could choose. Here are some of the most popular.

Jean shorts

Jean shorts, or denim shorts, are a style staple which suit women of all shapes, sizes and ages.

And, while you may not want to wear your denim shorts as short as the Daisy Dukes immortalized by actress Catherine Bach in the Duke’s of Hazard, there are plenty of longer options which would be flattering.

This pair of denim bermudas by Joes offer a laidback style which would be perfect for vacations.

Denim bermuda shorts

Black shorts

Ok, I know black shorts aren’t an actual style of shorts, but they are a very versatile option to have in your closet. They would be particularly good for pear shapes. By wearing a lighter colored top, you will draw attention away from the thigh area.

They can be dressed up or down. You can even wear a dressier pair of black shorts for work, with a blazer, depending on your office environment, or for an evening out.

This pair of Patagonia travel shorts would be perfect for vacation time. They have built-in 50+ sun protection and are water repellent.

Skyline traveler shorts

Black denim shorts

While you may traditionally think of denim shorts as being blue, you don’t have to stick to this shade. You could opt for a black pair instead to bring something a little different to your looks.

You can always wear a lighter, feminine top so your outfit doesn’t look too heavy for warmer weather.

This Mavi jeans pair are a nice mid-length.

Pixie roll cuff denim shorts

White denim shorts

Just as a pair of white jeans are a great option for summer, a pair of white denim shorts will be a lovely addition to your wardrobe for warmer months.

This pair from NYDJ promise to tuck in your tummy and lift up your rear, which sounds good to me!

Roll cuff pull-0n denim shorts

High-waisted denim shorts

If you like to make your legs look longer, or you have a torso which is long in proportion to the rest of your body, a pair of high-waisted denim shorts can be very flattering on you.

High-waisted denim shorts are particularly on trend this summer, with celebrities wearing them to festivals and bloggers showcasing them on Instagram.

But, they can also definitely work for the 40+ woman if you opt for a pair which are longer in the legs. High-waisted shorts look best with a shirt or blouse tucked into them.

This pair by Joe’s have a flattering indigo wash and are a mid-length with a high waist.

High-waist shorts

Work shorts

Depending on your workplace, if you are working, then you may want to look at a pair of shorts you can wear for work.

I find that a pair of tailored shorts in a darker shade works well. You can wear with heels and team with a smart blouse or shirt for a look which keeps you looking smart enough for the office but cool enough for summer temperatures.

This knee-length pair have great reviews on Amazon. I think they’d be a very versatile pair to dress up or down.

Fit pull-on modern city shorts

Dress capris

As well as wearing shorts for work, you could opt to wear dressier shorts, perhaps for a summer barbecue you are invited to, or for smarter venues and restaurants while on vacation.

Or, if you still want to be cool, but you want a more formal look, you could choose a pair of culottes or capris which come below the knee, rather than shorts. Then, you can wear with a heeled sandal.

Comfort fit capri with button detail

Long shorts

You may not want to wear shorts because you don’t like the way your thighs look, or simply because you don’t feel they are appropriate as you get older.

But, the right pair of long shorts can be flattering, especially if you are happy with the bottom legs.

Not only that, but longer length shorts are very on trend right now. I like the navy shade in this by of Gloria Vanderbilt shorts.

Stretch twill short with self belt

Flowy shorts

A pair of flowy shorts can be lovely if you prefer the material of your clothing to be loose and not to cling too much to your upper thighs.

These can be great for fitting a pear shape, or for balancing out an inverted triangle.

The floral print on this pair from Amazon would be lovely for holidays.

Floral print summer beach shorts

Short shorts – Best shorts for the beach

I still like my short short especially when I’m at the beach. It feels easy to wear with a colorful t-shirt and it just feels relaxed. Below is oneof my favorite shorts looks.

Pink chino shorts

If you are not keen on short shorts and don’t want to wade through dozens of pairs of short shorts, you can narrow down by mid length shorts and long shorts.

Final tips on how to wear shorts over 40

I leave you with some final do’s and don’ts when wearing shorts:

• If you’re petite, aim for shorter lengths unless you’re confident in your style.
• Don’t be afraid to invest a few dollars to have your shorts hemmed to the proper length.
• Don’t do short and tight together. If you choose shorter shorts, choose a baggier, looser style. And the tighter the shorts you choose, the longer they should be.
• An easy proportion rule of thumb on how to style shorts is: balance short shorts with a longer top and longer shorts with a shorter (or tucked in) top.
• Try tights under your dressier shorts for a polished, elegant look. A high boot or dressy flat finishes the look.
• Flat-front shorts are great for hiding your belly, as long as the fabric is supportive.
• When in doubt about length, go with a mid-thigh or just-above-the-knee length.

Prefer to wear longer pants? You may also like my article on how to wear capris and cropped pants.

What have you found to be the best shorts for you? Do you enjoy wearing shorts?

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