How to wear shorts over 40

I hate shorts. I have always hated them but it’s mutual, they hate me too.

I am all for wearing what makes you happy and it makes me happy to hide my white, thighs. In fact, it makes me very happy.

A lovely reader asked for some advice on shorts. So, I went out of my comfort zone (long jeans) and on a mission to decide what shorts I would wear, why and how.
How to wear shorts over 40

How to wear shorts over 40

  • It turns out the shorts that I would wear have daggy names like Berumda Shorts or, even worse, walking shorts. These shorts are longer than your arse but finish above the knees
  • Find the thinnest part of your legs, this is were you want the shorts to end. Lucky you can roll up, or cut off jeans to hit the exact right spot. I like the spot just above my knees.
  • I prefer fitted shorts instead of the gapping, parachute version. When the shorts are flush against your skin there is little chance of the wind blowing them up or them ride up when you are sitting, climbing, dancing etc.
  • Dress them up. I love casual denim short with a button up shirt, or sequins and heels. Break all the rules and have fun playing

Here are some great not-so-short shorts I found:

1. Sussan Walking Shorts $79.95 | 2. Mix Apparel Walking Short $20 (3 colours) | 3. Jeans West Adrienne Short $ 49.95 | 4. Country Road Stretch short $79.95 (8 colours) 5. Country Road D-Ring Culotte $129 (2 colours) | 6. Jeans West Christina shorts $49.95

How to wear shorts over 40

How is your relationship with SHORTS?


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  1. Those Mix Apparel ones are fab. I got some last year and they are much more expensive looking than they actually are. I also got some great ones from JAG at DFO. Though I don’t really like shorts much either but I find in Queensland they are quite practical.

  2. Natasha Andrews says:

    This is a very timely article for me – thanks for the advice and suggestions – I’ll be giving a few of these a try – maybe I’ve just been going too short when I have tried them on and the look has been NOT GOOD!

  3. Everything is too short for my legs too Rachel! I sing the praises of the Jeanswest curve embracer shorts – great length and fit because they snug in at the back and don’t leave a gap! Love the Sussan ones you are wearing. I have been looking for a fab pair of ripped denims that are not too short and these could well be the ones, thanks :)

  4. I love my shorts. Summer staple out here. I like them all lengths but mid thigh is probably my favourite length. I love a good denim short you can wear unfolded or rolled up. Wearing my very favourites from Jeans West right now.

  5. Lisa Mckenzie says:

    I don’t really do shorts I have an ugly right leg from operation scars and it swells an veins but wear dresses.tou look fab in them Rachel xx

  6. Every summer, Target does a bermuda short that sits right at the knee, is very fitted and flattering.

  7. I have a pair of Susan denim tight shorts to the knees with a tiny roll up and every year I pull them out to wear God help me when they ever wear out!

  8. For what it’s worth you look great in those Sussan shorts! You need good legs for shorts, last time I wore them I’m guessing I was about 14 (now 39)!

  9. you crack me up Rachel!
    I’m with you on shorts, but you’ve made me think;0 … I’m going to cut of some jeans at that same level. you are inspirational hun! … love it! and love how your puppy is looking at you!
    have a good one! love m:)X

  10. You have actually inspired me to go and look for a pair of shorts! I never wear shorts…

  11. I love shorts but have been game enough to wear ones a little shorter over the years. Great post. V x

  12. Shorts and me aren’t a good mix but if I were to wear shorts I think long denim ones would definitely be my best option.

  13. Thanks Rachel. Your post has made me think too. I don’t really think twice about wearing short dresses or skirts (just above the knee of course, being over 40 and all that!!), but don’t wear shorts anymore. It would be far more practical, especially with 2 young children to wear shorts so I am definitely going to check some of these outs and overcome my fear of them! Thank you.

  14. Parisgirl says:

    Last summer I bought a pair of navy shorts from Big W for $8. Yep $8. They are a great length and so flattering. The material is on the soft side and launders well. They will never win any awards but for the price they are excellent to wear to the shops and around home. I am intending to look to see if they are on the rack this year. Amazing what you can get or $8 isn’t it?

  15. I’m on blog catch up! Loving your denims and I’m going to check those babies out as I need some!! I’ve only got fairly short ones which are fine when I’m standing but I hate the way they ride up when you sit. Plus I have to use copious amounts of fake tan whenever I wear them which is never practical. x

  16. My version of how to wear shorts goes something like this:
    1- Go to shops, look for shorts that appeal to you
    2- Buy shorts in the size you are
    3- Remove any tags and stickers (voice of experience here!)
    4- Put them on and hope for the best
    Voila! 😀

  17. You have great legs so I’m surprised you are not a fan of shorts. I have a love hate relationship with them at the moment. Can’t seem to find a style that suits and I feel comfortable in.

  18. Shorts are not my friend. They tend to make like legs look like two very short tree stumps. But you’ve got some great tips and styling advice in there, so you never know…maybe this year I’ll find a pair of shorts that look ok after all!!

  19. Shorts and me have hate/hate relationship. I do have a few pairs but hardly every were them as they emphasise my huge thighs and calves far too much…so for the most part I’m sticking to frocks! xx

  20. Love this piece! I found some cute 50s style high waisted (not too short) shorts at Portmans last week.