Dressing Up An Athleisure Jumpsuit

Our chances to dress up or reasons to make an extra effort with our appearance has been seriously limited these days.  Comfortable and easy-to-wear have become the name of the game for most of us these days so I take my opportunities whenever I find them. It’s usually a trip to the supermarket, pharmacy, or doctor appointment. I used to describe my errands as “have to’s” until I reread this book by Gretchen Rubin, which reminded me I “get to” do these things. Do you look at life that way?over 50 fashion blogger Jennifer Connolly showing how to dress up a athleisure jumpsuit

I discovered this jumpsuit here.  One reader said she almost didn’t open the post because it talked about athleisure clothes. I admit I haven’t always been a fan, but times are changing so I’m finding a way to make it work for my style.

OK, back to this jumpsuit. For hanging out at home, I wear it with comfy flip-flops ( horrors, yes I wear this orthopedic pair), and a pair of earrings. Karl Lagerfeld is famously quoted as saying, “I am physically allergic to flip-flops”, but I’m guessing he didn’t have my feet or live my lifestyle. These provide metatarsal support and are ideal for low arches and flat feet.

To dress it up I topped it with a classic linen jacket, added a belt, and switched to very comfy, cork wedge sandals. I also covered the drawstring waist with this woven belt that I picked up during a laundry supply run at Target. I opted for a large so it would be long enough to wrap and tuck it after I snaked it through the buckle.
jennifer connolly wearing dean davidson earrings with white linen blazer

If I topped this with a white cardigan, it wouldn’t have had the same effect as this blazer. Cardigans are super comfy, offer arm coverage but are infinitely more casual. This is the type of blazer you may have hanging in your closet from your work wardrobe. Just because your lifestyle has changed doesn’t mean your workwear or more formal pieces can’t be worn.

I’m also wearing these fabulous earrings from Dean Davidson and a tiny rose-gold bee pin. Stay tuned for my post on Dean Davidson’s amazing designs plus a very special discount for my readers.

Have you embraced athleisure wear? Have you experimented with dressing it up?

Thanks for reading and remember to wear what makes you feel confident.

This post may contain affiliate links which won’t change your price but will share some commission.


  1. Mary Ann Doerzbacher
    August 21, 2020 / 12:39 pm

    Your bee pin immediately brought to my mind the recent (August 9) sudden passing of fashion stylist, Brenda Kinsel from Sonoma CA. She loved bee pins, anything with bees. I totally enjoyed her Facebook posts and columns devoted to “fashions for women over 50.” Deepest condolences to her family.
    I will miss you, Brenda.

  2. - Vicki Mikola Dack
    August 21, 2020 / 5:38 am

    What a Snappy looking outfit! Personally don’t wear “jumpsuits” — just don’t like stepping out of the garment and hanging it on the jacket/purse hook to use the bathroom .

  3. Beverly the Inspired
    August 20, 2020 / 1:48 pm

    Clever idea topping the jumpsuit with a blazer & defining its shape with a belt. Chic! The bee pin is a sweet addition.

    Only wear a jumpsuit for yoga & Pilates. Keeps things I want covered covered *grin*. Once we can have classes again, upping the chic factor with blazer/belt will be perfect. Sometimes we’ll go for coffee or I go marketing afterward. You’re right, a cardigan or vest over seems “casual” like I tossed it on to hide “gym clothes”.

  4. Nancy
    August 20, 2020 / 12:54 pm

    You have definitely found your perfect red because it flatters your skin tone and lip color. Beautiful lipstick compliments the outfit. I think jumpsuits are perfect for shorter women because they give a long continuous line of color. Everyone should have one or two in their wardrobe.

    • Jennifer
      August 20, 2020 / 2:50 pm

      I agree…they are the ultimate column of color

  5. Barb
    August 20, 2020 / 12:19 pm

    I looked for this online when you first posted it but it was out in 🇨🇦 But is now stocked. I am about your shape, size and weight. What size and leg length did you get? Unfortunately the burgundy isn’t available up here but the black is nice as well

    • Jennifer
      August 20, 2020 / 2:49 pm

      I am wearing a small, my daughter bought the medium because she is 5’9″. I just bought the regular length.

  6. Cyndi
    August 20, 2020 / 10:25 am

    Thanks for the ideas to dress up the jumpsuit…could easily adapt for pants and a top in a column of color. The link for the belt took me to a Wolf and Badger pin (cute but not a belt) I haven’t tried the jumpsuit trend because it seems unwieldy for trips to the bathroom. What your opinion after wearing one?

    • Jennifer
      August 20, 2020 / 2:47 pm

      I avoided them for the same reason but I’m finding this one very easy, perhaps because it’s a soft knit that just pulls up with no zipper or snaps

  7. Mumbai
    August 20, 2020 / 9:58 am

    You have a wonderful smile

  8. jmp
    August 20, 2020 / 9:53 am

    I haven’t worn a jumpsuit since the 70s , but I think I’m going to try one on now. This one looks terrific on you, and the blazer is a great idea.

  9. Pam Sledge
    August 20, 2020 / 8:13 am

    You look great in this and your hair must like Vancouver.

    • Jennifer
      August 20, 2020 / 9:15 am

      We took these pictures in CA. I am still inside, quarantining in Vancouver so I don’t know what it will do to my hair:)

  10. Nicole
    August 20, 2020 / 7:52 am

    Your post reminded me of a beautiful knit jumpsuit I have owned for a couple of years and only worn once. It is comfy and flowy and just the perfect garment to wear in the 100+ weather we have been having. I was thinking of this jumpsuit as something to wear for dress-up occasions, which of course are not happening. I put it on right after reading your post and am so comfortable and cool! And I am definitely not too dressed up for staying home!

    • Jennifer
      August 20, 2020 / 9:16 am

      Yay, that makes me so happy Nicole!

  11. Deanne
    August 20, 2020 / 7:49 am

    You look terrific Jennifer! Never tried jumpsuits but if they had this one in my size I would.

  12. Dianne
    August 20, 2020 / 7:27 am

    Outfit is lovely for being Athleisure😀 Color is stunning on you! Being here in Florida we are still hunkering down, COVID-19 is still very much a part of our lives. Hope your trip to Vancouver is going well with your daughter.

    • Jennifer
      August 20, 2020 / 9:16 am

      I am surprised to love this color:)

  13. Joanna
    August 20, 2020 / 7:27 am

    I would not have thought to wear a blazer with such a casual jumpsuit. I’m going to copy you, if you don’t mind. Love that photo of you having a good laugh. I think your hubby can always make you laugh.

    • Jennifer
      August 20, 2020 / 9:17 am

      Go for it. My daughter took these pictures:) They both make me laugh

  14. Rose
    August 20, 2020 / 7:21 am

    Love the jumpsuit on you! I haven’t tried one on in years, might have to change that. I am happy to be able to dress up even a little bit just to go the store. It used to be such a chore.

  15. Mary Lou S
    August 20, 2020 / 6:54 am

    I bought this jumpsuit after seeing your earlier post. I loved jumpsuits back in the 70s and thought I would never wear one again. I am a couple inches shorter than you so it is a little longer on me and I bought the charcoal color. I love the way you have styled it, you look amazing.

    • Jennifer
      August 20, 2020 / 9:18 am

      I am wearing the charcoal one today:) I love them. Thanks so much, Mary Lou

  16. Suzanne
    August 20, 2020 / 6:32 am

    Great outfit! Looks terrific on you. Does not look “athleisure” at all!

  17. Doris Harding
    August 20, 2020 / 6:32 am

    Love all these shots of you and this jumpsuit – you look so beautiful! Unfortunately I can’t wear jumpsuits because I have an exceptionally long torso and none of them fit at all. Nevertheless, your tips on accessories are “right-on.” Keep up the good work and continue showing these wonderful dressing/accessorizing ideas!

  18. Linda
    August 20, 2020 / 6:32 am

    You look marvelous! I love all of your combinations for this outfit!

  19. MRSBEN2
    August 20, 2020 / 5:56 am

    LOVE how you have accessorized it and very cute. Like Trish though, would pass on it because of its cropped leg length as probably would be shorter on myself. (Sad face.)
    P.S.: Enjoy your time with your daughter.

  20. Kathy
    August 20, 2020 / 5:32 am

    I love this look on you! To me it doesn’t scream “athleisure“.

  21. Jan
    August 20, 2020 / 5:18 am

    You could devote an entire week to your question, “do you look at life that way”. I read somewhere that life is complicated and if you’re waiting for things to be perfect before you can be happy, you will run out of time.
    I love your dressed up, casual look today! You’re showing us how to adapt to an ever changing world in which our daily activities have been drastically upset. Keep an open mind, accept change and keep moving forward.
    I am most definitely going to adding these casual pieces to my wish list.
    Thankyou for keeping us current Jennifer! I want to face each day with eyes and mind wide open.

    • Jennifer
      August 20, 2020 / 9:22 am

      Such a wise observation, Jan. I have a lifetime of training to undo in order to look at life that way…and there’s no better way to start than now:)

  22. Lidia
    August 20, 2020 / 4:54 am

    Love this on you…I would love it on me too but my size isn’t available in any colors that work…boooo

    • Jennifer
      August 20, 2020 / 9:23 am

      Keep an eye out for restocking or similar garments from other brands.

  23. Leslie
    August 20, 2020 / 4:21 am

    Good morning Jennifer!! I hope your trip with your daughter is going well. I love this little jumpsuit and bought it earlier in the summer in the charcoal color. I styled mine with my Jean jacket and some slip on sneakers. The pretty wine color looks so nice on you with your hair and skin tone. I am definitely going to try a belt or scarf around the waist to add a little interest, thanks for the inspiration 😉

  24. Trish
    August 20, 2020 / 4:11 am

    This outfit is so great. Not sure I could wear with the cropped leg. LOVE the photo of you in the shade with your chin up. Kudos to the photographer.

    • Jennifer
      August 20, 2020 / 9:30 am

      My daughter took these. She’s a great photographer so I am lucky to get her help.

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