Don’t shop for your shorts based on your age. There, I’ve said it. If you don’t read any further, please remember this. Instead, when selecting shorts over 50, consider your height, body shape and proportions. That’s what will give you a look that you’ll love.
But seriously, be open to what looks best for your body type. I know that “at this age,” there are lots more issues like spider veins, crepey skin, you name it. (trust me, I understand!). Let’s put those issues aside for the moment. I encourage you to try on different shorts styles until you find the one you like best. There are self-tanners and leg makeup that can help you work through that. But if you’re that uncomfortable, pick a style that makes you feel confident. That’s what’s important and I am here to help.
I’ll share some styling tips and then offer a round-up of the best short styles I’ve found for you to shop from. I’ve even included some shorts alternatives, if you find that shorts really are just not for you.
This post was updated on 5/11/26. All product links are new and active.
**This post contains affiliate links, and I will be compensated if you purchase after clicking on my links.
Find the Right Fit (The Key to Flattering Shorts Over 50)
Shorts may seem like an easy purchase, but the right fit makes all the difference.
Start with the leg opening. You want it to skim your leg, not feel tight, but not overly wide either. A balanced fit will always look more polished. As a general guide, you should be able to pinch about an inch of fabric at the leg. Anything significantly more can start to look too loose and less intentional.
Fabric also plays an important role. Structured fabrics tend to hold their shape and look more refined, while softer fabrics can feel more casual.
Finally, think about balance. A looser top pairs well with more tailored shorts, while a more fitted top can complement a slightly relaxed style.
It’s All About Proportion
This is what makes an outfit feel balanced and intentional.
You may have heard of the “rule of thirds” when it comes to fashion. Quickly defined it means dividing an outfit into three parts, aiming for a 2:1 ration. So, two-thirds of the outfit’s overall visual space should be dominated by one piece, while the remaining one-third is another piece. This is easier to visualize with pants and skirts, since they cover most of the body. Shorts are a little bit more difficult. Keep in mind that the rule of thirds is about the clothes, not the body. It’s about creating visual balance through the use of clothing.
The visual break should ideally not be placed in the exact middle of the body, but rather at the one-third or two-thirds mark. This is why I don’t like how Bermuda shorts fit my frame. As you can see in the image below, the blue shorts outfit on the left easily fits into the rule of thirds. Keeping my outfit monochrome also helps create that 2/3 look at the top. But even if my top were a different color, the shorts are short enough to allow 1/3 of my lower body to show.
Contrast that to the Bermuda shorts look. I styled this look the way I would wear it — with my shirt tucked in. However, when I do that, it divides my body into halves, with little space below the shorts to elongate my legs. I chose the nude sandals to help with the illusion of a longer leg but they still look shorter compared to the outfit on the left, even with sneakers.
To help with proportion, I could have chosen to wear a longer top with the Bermuda shorts. Wearing a top that lands lower on the hips would have created more of a 2/3 look on the top, but that’s not a look that suits my style. So, I just typically avoid Bermuda shorts for myself.
Shorts Over 50: Choosing the Right Length
Inseam is probably the number one concern regarding selecting shorts over 50. There are three standard lengths of shorts:
- Short (2 – 3″ inseam)
- Midrange (3 – 5″ inseam)
- Bermudas (9 – 13″ inseam)
When I started this post with “don’t pick your shorts based on your age,” I meant that being over 50 doesn’t mean that you have to wear Bermudas and cover as much of your leg as possible. But they might be perfect for you if you’re six feet tall.
Midrange shorts are the most universally flattering and are what I wear. When I am shopping for shorts, I look primarily for a 4″ – 5″ inseam. I will wear a 3″ inseam if they are more casual or athletic.
Shorter shorts are best for petite women because they make their legs look longer. As I mentioned, taller women can pull off Bermuda shorts better than most. Personally, bermudas just don’t look good on me. I am only 5’3″, and they make me look even shorter. It’s all because of proportion. So let’s talk about that.
How to Choose the Right Shorts for Your Body Type
The right pair of shorts isn’t about your age, it’s about finding the best fit for your body.
- If you carry weight in your midsection:
Look for mid- to high-rise shorts with a smooth front. A slightly longer length, like a mid-thigh or Bermuda, can feel more balanced and comfortable. - If you have fuller hips and thighs:
Choose shorts with a bit of room through the leg. A-line or slightly longer styles can help create balance and a more streamlined look. - If you have an hourglass shape:
Structured styles like trouser or chino shorts work beautifully. They highlight your waist while keeping your overall look polished. - If you’re petite:
Look for a slightly shorter inseam and a higher rise to help elongate your legs and keep proportions balanced. - If you’re tall:
You can easily wear longer lengths. Tailored Bermuda or mid-length shorts can look especially chic and intentional.
Try Them On, Be Particular, Sit in Them!
So, I’ve had some shorts that I love how they look when I am standing, but when I sit down, they can rise up to the middle of my thigh, and I constantly have to pull them down. Or, I’ve been at a party and had to keep my napkin on my leg.
So, whether you’re shopping in-store or ordering online, make sure you sit in your shorts before making a final decision. I also recommend checking the rear view of your shorts and bending over – I think you understand whyl
5 Key Takeaways for Wearing Shorts with Confidence
- Fit comes first
Shorts should skim your body. They should not feel tight or overly loose. - Proportion is everything
The right length creates balance and makes your outfit feel intentional. - Fabric matters
Structured fabrics tend to look more polished and hold their shape. - A little shape goes a long way
Avoid overly baggy styles. Clean lines always look more refined. - When it feels right, it looks right
Confidence comes from wearing something that fits you well.
Shorts Over 50 Alternatives
If you don’t want to wear shorts and pants are just a little too warm for you, consider a skirt or skort. Either one will keep you cool and stylish. With the sporty trend in full swing this season, an athletic-looking skort is a great idea. It’s casual, can be a little longer than shorts, but you have the comfort of knowing that a short is underneath.
Scroll down to see my recommendations on both skort and shorts alternatives.
What if I Don’t Like My Legs?
As I mentioned at the top of this post, spider veins and crepey skin are real issues, especially over 50. On a recent segment on WGN-TV, I was asked about what to do about bare legs and I gave away my secret of using leg makeup. I use the Sally Hansen leg makeup which provides great coverage and does not rub off on your clothes (or sheets). It takes a little practice to get it looking natural but it’s easy once you get the hang of it. A tip: make sure your legs are as moisturized as possible. That will really help get the results you want.
Here are my three favorite products to minimize those problem areas. I have used all three of these with great results.
Shopping for Shorts Over 50
Here are lots of looks for you to shop from, in all different lengths and styles
Shop My Looks:
Midrange Shorts (3 – 5″ Inseam)
Longer Shorts (6-8″ Inseam)
Bermuda Shorts (9-13″ Inseam)
Short Shorts (2 – 3″ Inseam)
Denim Shorts (All Inseams)
Shopping for Shorts Over 50 Alternatives
Here are some stylish alternatives. I kept it casual so that you would most likely wear these skirts and skorts the same places you would wear shorts.
Athletic Skorts
Denim Skirts
Colorful Skirts
White Skirts
Midi and Maxi Skirts
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