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 learn towards one of the 5 different body shapes: apple, pear, rectangle, inverted triangle and hourglass.
Certain shorts will work better on one shape over another. Keep your shape in mind when looking at the styles below.
For instance, you might want to think about a darker colored pair if you are a pear shape, or a pair to fit your curves if you are an hourglass.
Eileen @eileenternullo above chooses a retro style for her shorts outfit.
Get her look with this similar shirt, shorts (another option here), espadrilles, handbag and hat.
If you don’t know your body shape, read our article on how to find your body shape.
Height can also add to the variable of how to choose the 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. Remember, for the most flattering silhouette you want to get a 1/3 – 2/3 balance within your outfit and / or within your overall look. (to learn more about this concept check our article on how to wear capris or take the 21 steps style course where we explain this concept in a lot of detail.
Not being comfortable with showing your legs is probably the top reason most women don’t want to wear shorts. And of course the choice if doing so is completely up to you. But if you like the comfort of wearing shorts, and want to wear them despite being reluctant to show your cellulite, veins, scars or other issues, there are solutions.
My favorite solution is just to choose comfort over vanity and don’t care about the way your legs look. That is always a choice! If you wear your shorts with confidence, people will notice YOU and not your legs.
However, if you’d rather not showcase you legs, opt for a longer short style.
You can also consider wearing a pair of lightweight tights under a shorter pair of shorts. Wearing tights can be a fashion statement or it can be a way to smooth and conceal veins or scars. The ones Spanx makes will also conceal will also smooth the body fat in your legs.
Sandra @lapecosapreciosa above makes her print pants the star of her outfit by wearing them with a plain black tank top.
Get her look with this similar tank top, shorts (another option here), sandals, woven bag, sunglasses and belt.
What length is best for shorts for women over 40?
Just as there are many skirt lengths to choose from, anything goes when it comes to the hem length of your shorts.
There were plenty of short shorts on the catwalks for summer and for fall 2022, but also stylish longer length shorts.
So, simply choose the length that flatters you, and which you are comfortable with.
What are the best women’s shorts and most flattering shorts for each shape?
Most of you will only wear shorts for summer or for your vacations. I also like to wear shorts as loungewear as I just find them very comfortable.
Let’s break shorts down into current styles and who they’re best for.
UTILITY women’s shorts – Best shorts for a safari holiday
Khaki shorts are ideal for a safari holiday or a walk in the park.
If you love a natural look, then khaki shorts would be a lovely option. I can definitely imagine Jennifer Aniston wearing these ones.
PAIGE Brooklyn High Waist Utility Shorts
Or, you could opt for a utility style in a blue denim.
Massimo Dutti Linen Cago Shorts
Similar shirt, shorts, shoes and hat
Above is how I wore mine during my holiday in Namibia.
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 often 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.
Open Edit High Waist Pleat Front Shorts (plus size)
Similar top (other options here and here), shorts and flats
I find my high waisted flare women’s shorts particularly good for more dressy occasions. Above is how I wore mine on a holiday during the evening for a stroll on the boulevard and outdoor dinner.
Best women’s shorts styles: 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.
NYDJ Briella Roll Cuff Denim Bermuda Shorts
The pair above 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.
Best women’s shorts: 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 part of your legs.
Not only that, but longer length shorts are very on trend right now.
Lands’ End Flex High Rise 10″ Shorts
Best women’s 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. These can be 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.
Diane @fashiononthe4thfloor (read her style interview here) wears a pair of wide, knee-length shorts with her crop top.
Recreate her outfit with this similar top (another option here), shorts (another option here), slippers and sunglasses.
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 may want to tuck in your top and add a belt. This is a great dressier style that can be paired with a lightweight sweater or a jacket for a short pants suit.
Lands’ End High Rise Bi Stretch Pintuck 11″ Shorts
Similar shirt, shorts, sandals, sun hat and necklace
In the photo above, you can see how trouser shorts can be given a dressier look.
More types of shorts
While these are the main styles of shorts you could opt for, there are of course lots of types of shorts within those categories that you can choose. Here are some of the most popular.
A paperbag style usually has a higher waist, which is particularly useful if you want to make your legs look longer.
Wit & Wisdom Paperbag Waist Linen Blend Shorts
You may be looking for a pair of lounge shorts because you are at home much more than usual at the moment, or because you would like a pair of shorts to exercise in.
Either way, the Felina shorts (below) are very comfortable and come in a choice of neutral shades, making them some of the best women’s shorts to choose for a more casual look.
Felina Stretch Organic Cotton Lounge Shorts
Do you love to walk around your neighborhood, or further afield? Whether you’re heading out for a few errands, sightseeing (when you’re able to travel again) or you like to get out for a longer hike, the outdoor shorts below are very well-reviewed, with reviewers saying they are the perfect length for exercising – not too long, and not too short!
They’re also a great choice if you like yoga or pilates and you don’t want to wear longer leggings when the weather starts to warm up.
BALEAF 7″ Liner Athletic Workout Shorts
Just as chino pants are timeless enough to wear year after year, so too are chino shorts.
Lands’ End Stretch Chino Bermuda Shorts
Nikki @midlifechic above wears a pair of classic chino shorts, and accessorizes with a zebra!
Recreate her outfit with this similar tank top, shorts, walking shoes and backpack.
A pair of printed shorts could be the perfect way to add interest to your outfit. The Ted Baker shorts (below) would add an elegant look to your shorts outfit.
Ted Baker London Ayaaz Floral Print Belted Shorts
Or, you could choose a more casual pair of shorts like the Boden shorts (below).
Boden Linen Shirred Waist 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.
Wit & Wisdom ‘Ab’Solution Retro High Waist Denim Bermuda 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.
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 BLANKNYC (below) is a timeless classic you are likely to wear for many summers to come.
BLANKNYC The Warren Raw Hem A-Line Denim Shorts
If you love wearing white during the summer, also take a look at how to wear white pants.
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 (read what I have to say here about your vertical body type), 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 a little longer in the legs. High-waisted shorts look best with a shirt or blouse tucked into them.
Wit & Wisdom ‘Ab’Solution High Waist Denim Utility Shorts
Adaline @sdmomstyles above wears her shirt tucked into her denim shorts.
Get her look with this similar shirt (another option here), denim shorts (another option here) and sandals.
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.
NYDJ Side Slit Capri Bike 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 flowy skort (below) from Amazon would be lovely for vacations or sunny days in the garden.
STRETCH IS COMFORT Flowy Skort
Or, you could also wear flowy shorts for exercise. The shorts below have a skirt on top. Reviewers say they are flowy and super soft.
If you want to make your shorts outfit look and feel more luxurious, like one of the silk options below.
Natori Boro Cotton & Silk Shorts
Linen is always a lovely, light material for summer, making linen shorts ideal for a warm weather vacation.
Arket Knee-Length Linen Shorts
NYDJ Linen Blend Bermuda Shorts
The perfect mid length is often hard to find when you’re searching for the best women’s shorts. You could try the Madewell pull-on shorts.
Madewell Clean Linen & Cotton Pull-On Shorts
Lands’ End is a good place to look for shorts as you can choose depending on the rise.
Lands’ End Starfish Mid Rise 7″ Pull On Shorts (plus size)
Psyche @economyofstyle above opts for mid thight shorts, and dresses them up with heels.
Check out this similar shirt, shorts (another option here), peep-toe booties, handbag and fedora.
I still like my short shorts especially when I’m at the beach. They feel easy to wear with a colorful t-shirt and it just feels relaxed. Above is one of my favorite shorts looks. 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 on Nordstrom.
BEST SHORTS FOR THE BEACH
Or, if you want to swim in shorts, how about a pair of board shorts?
Lands’ End 5″ Sustainable Elastic Waist Board Shorts Swim Shorts with Panty
See our top picks for the best bathing suits for women over 40 this summer.
Another option could be to look for a pair of shorts which look like a skirt. That way, you can get away with a shorter length of skirt, secure in the knowledge that you won’t be flashing anything you don’t want to when you sit down!
LouKeith Athletic Activewear Skort
Depending on your workplace, if you are working right now, then you may want to look at a pair of shorts you can wear for the office.
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.
I think the COS shorts (below) be a very versatile pair to dress up or down. They also come up with a matching blazer
COS Tailored Linen-Blend Bermuda Shorts
Or, you could choose a shorts and blazer set that is already put together for you. The blazer set (below) comes in 9 different colors, and reviewers say it is great quality and super comfortable.
Final tips on how to wear shorts over 40
I leave you with some final do’s and don’ts when wearing shorts:
- Don’t be afraid to invest a few dollars to have your shorts hemmed to the proper length. You’ll probably wear them year after year, so it will be worth it.
- 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.
- Flat-front shorts are great for not adding extra bulk to the tummy area
Shop the items above here:
Do you enjoy wearing shorts? What are the best women’s shorts brands and styles you’ve found so far?
- How To Wear Capris And Cropped Pants – An Extensive Guide!
- How To Wear Leggings Over 40 – A Complete Guide
- How To Wear White Pants: Inspiration And Ideas
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Feature image by Sandra @lapecosapreciosa
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This is a great article. Thank you for covering the Bermuda vs. Pant Short as well as discussing the Work Short. I had lumped everything under Bermuda but knowing the difference I can now look up the others which is great because Bermudas are a little tight in the waist for this apple.
I really enjoyed this article and cannot wait to wear shorts this summer. I wear board shorts to swim, as I feel much more comfortable in them compared to bikini bottoms. Otherwise, it is long shorts for me now. I have a black dressy one for evening, that I wear with barely there flat or mid-heel sandals, a silk white/cream top and a thin gold chain belt, and a sporty one, in beige/stone. I think you are absolutely right that the slimmer the fit, the longer the short should be. I look best in slim fit shorts so I wear them knee-length or close to that.
I used to love wearing shorts. My legs are veiny. I might give it another go and not worry too much about the veins.
I have always loathed wearing shorts. I’ve never considered myself to be a large person but my entire life shorts have ridden up on the inside of my legs. It’s unflattering and makes me feel horrible and uncomfortable in public. I’m an hourglass shape and just on the tall side of petite so if it fits my waist the leg opening is never wide enough. If you ever have advice on people with athletic legs (aka bigger thighs and calves), I’m all ears.
I’m a sailor. A bohemian mind and country heart. My legs are my asset so long ones make me feel really dumpy. But I’m 42 and the 3” length is probably not supposed to happen. How do I find a happy medium?
If your legs are your asset I see no reason why you can’t stick to the shorter length!
i love any kind of style short pants old or new style
I bought two bermuda shorts last year and when I saw the photos afterwards, decided to give up on them. They make me look like a man. I wasn’t a shorts’ person when I was young and I won’t become one now.
It’s nice to see this post. I love wearing shorts!!! I work in a school office and I am able to wear them during the summer to work. I have found the Dana Buchman bermuda shorts from Kohls the most flattering for me.
I have a generous gut and inner thighs and wrinkly knees… There are no shorts to help here!! I’m sticking to fitted capris and tunic tops!
I need shorts that fit my waist and my hips at the same time. I have the same issue with pants.