How to Wear Shorts Over 40

Sheree Frede in Talbots lemon shorts and button up top

Summer is right around the corner and with being in Sanibel so much I am enjoying getting a little SAFE sun in my evenings! As you all know I am a major fashionista, I am now getting creative and using my walking time as an excuse to not look so….homely! With that being said I am pulling out my summer tops and my cutest shorts. Below I have featured all of my favorites and most are budget-friendly!


Sheree Frede in Talbots lemon shorts and button up top

Shorts + How to Wear

Wearing shorts or denim shorts does not have to be as stressful as we make it. The right length for your body is the key here! I have a few tips for what I find that help me to look and feel my best in my shorts. I know I constantly hear from you ladies that you hate your knees or the skin on your legs and I am right there with you. One thing to keep in mind when wearing shorts is – when in your life have you EVER heard someone say “wow, she has really pretty knees”? Probably never, at least I have never heard that! So do keep that in mind and stop beating yourself up, girlfriends!!

Choose The Right Length

You don’t have to be stuck wearing long baggy maw maw pants if you’re over 50! I will say, length is crucial when choosing the type of shorts that will look best. The medium and longer-length shorts are more flattering and slimming. I love the 7″ length chino shorts that J Crew has in their shorts lineup. They hit the pretty part of the thigh, but they also do longer shorts. The “pretty part” of the leg to me, starts about 2/3 inches above the knee.


Pair Them Properly

The way you pair your shorts can determine a lot. Choose the right top to go with your shorts. Avoid short, skimpy tops and go for something that offers a little more coverage, the tops above are perfect to rock with your shorts. I always say when you show leg, cover more of the upper body – no tummies! Unless that’s your thing, then do you GF!

Avoid Shorts That Are Too Tight

SheShe by airplane wearing denim shorts


Ladies, the same goes for shorts that go for all fashion. Avoid wearing them too tight!! Pick a loose-fitting style that is more forgiving around your thighs which may have lost a little bit of their youthful elasticity. We are trying to look and feel our best, but forcing our bodies into certain short styles is not going to do the trick! Luckily for us, the mom/dad and vintage-style jeans are trending and extremely flattering!

Slim Down Shorts

Sheree Frede in shorts and vegetable top
Sheree Frede in shorts and vegetable top


A trick I have learned for looking slimmer is to add a pretty heeled sandal or small wedge! Just a small heel will do the trick. Everyone has a personal preference and I personally do not think wearing a huge wedge or heel while in short shorts is very ladylike! So keep in mind the length of your shorts when you are pairing your shoes…and to each their own!!



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Have a wonderful day sweet friends!


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