Challenging My Style Formula

Challenging My Style Formula

I’ll just file this post under never say never. I’m open-minded about fashion and love to try new looks but I haven’t worn shorts for as long as I remember. There’s nothing wrong with shorts and they’re a big part of many women’s summer wardrobe. I simply stopped wearing them in my 30’s and didn’t revisit the look. They feel preppy which isn’t a style I wear.

I succumbed to the lure of shorts last week because they were the perfect thing to wear. Luckily, I was using favorite self-tanner, every other morning, so my legs didn’t have that white, pasty look.

I bought the shorts for a Walmart post and figured this was a great price point to dip my toe into a new look.Jennifer Connolly of A Well Styled Life wearing Walmart shorts and denim shirt on boat

This day wasn’t super hot but it sure was sunny. We were exploring Sooke, Metchosin and several other small towns along the southern coast of Vancouver Island. My husband is a boat lover so we stopped at several docks to check out the sailboats.

These earrings are a style departure for me too. I wasn’t sure I would love them but I do. They’re super light and the colors go with everything.Shorts styled for comfort by Jennifer Connolly of A Well Styled Life

This Bermuda length doesn’t feel too different from my knee-length denim skirt. But because I’m short and my legs are proportionally shorter than my torso, I’ll be trying on shorter lengths. Style blogger Jennifer Connolly of A Well Styled Life wearing bermuda shorts from Walmart

It’ll be blistering hot when we get home and there’s tons of work to do on our house so I see more shorts in my future.Jennifer Connolly of A Well Styled Life wearing white sunhat, denim shirt and white shorts

BTW- arthritis in my hands is making it painful to put on and take off my bangles so I am stacking elastic bracelets these days and find it a fun look for summer.

What style have you challenged yourself to that’s out of your comfort zone?

Thanks for reading and have a great day.



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Affiliate links within this post may generate income for AWSL at no additional cost to you. When you shop through my links, I earn a small commission which helps support my business.


  1. Laura
    July 18, 2019 / 4:21 am

    I know it sounds silly, but for many years I didn’t wear button-front blouses because they never seemed to fit correctly. I recently found several that fit and I’ve incorporated them into my wardrobe. I tend to tie them at the waist as you’ve done in these photos, as I think it’s more flattering on my short torso. I love the no-iron shirts from Chico’s!

    • Jennifer
      July 18, 2019 / 8:15 am

      It doesn’t sound silly to me. Many front button front shirts gap because the buttons are poorly placed. I avoided them for years too. Now I look for ones with a button level with the widest part of my bust line. It makes all the difference.

  2. July 18, 2019 / 4:42 am

    You look great in these Bermuda length shorts ! I don’t really see an extreme proportion issue with your legs vs torso. Love the earrings, love the denim shirt and wow….summer! Enjoy your vacation….

    • Jennifer
      July 18, 2019 / 8:15 am

      Thanks Paulette xx

      • Carolyn
        July 18, 2019 / 9:52 am

        Never really gave up shorts. My favorite is a pair of Lee white shorts that are about 2 inches above the knee. With short legs, like you said, need to get the length right . I think you wear them well!

        • Jennifer
          July 18, 2019 / 10:57 pm

          Thank you Carolyn

  3. Ann
    July 18, 2019 / 4:49 am

    Why do we struggle with the thought of wearing shorts? I feel that way also. I do wear Bermuda’s and/or skorts, especially golf skorts. As an aside, I love the color of your lipstick! Do you mind sharing the source/color? Love you posts!

  4. July 18, 2019 / 4:53 am

    Great, relaxed look – better than denim skirts (looks a bit outdated on a boat…). Bermudas are favourites – they suit most figures, ages and styles. And your legs are not short – whoever told you that? Love your blog by the way. Have happy, lazy, carefree summer days. All the best from Eva Sundene in the Canary Islands

  5. Barbara
    July 18, 2019 / 4:57 am

    I have the exact shorts in khaki. I also have arthritic hands and these are easy on and off. The price is perfect and they seem good quality. Walmart has really improved their clothing line. I don’t wear many button blouses as it’s difficult for me to fasten. Tee shirts and tunic tops are the best for me. Luckily they are in style. When it gets hot, we’re having 90 degree temps with a 90% humidity, I wear dresses. Let’s the air flow on the body, swing dresses work for me in the hot weather.

    Love those shorts as I also have then them in khaki

    • Susan Gowan
      July 18, 2019 / 7:02 am

      Funny you should bring up the shorts topic this week. I have avoided shorts for most of my life due to scarring from an accident. It has been ruddy hot where I live so I have been wearing culottes and capris a lot to swimming and even a family event on Sunday. Not as big an event as I used to think. Number 1 rule at my age: 68. Be comfortable and wear what you like. Thanks for that timely piece. I love Sooke btw.

  6. Susan
    July 18, 2019 / 5:32 am

    I also do not see the short legs/longer torso problem at all looking at your full on photo. This is a cute, flattering outfit. My Mom always said the legs are the last to go, so go for it! Love the earrings too. I may have to check out the shorts-I previously bought the t shirt dress from Walmart and am super happy with it.

  7. Lynn
    July 18, 2019 / 5:56 am

    You look great in shorts!

  8. July 18, 2019 / 5:56 am

    Hey, you look great in the shorts! I think this is a great length and more wearable for many of us.

  9. Rose
    July 18, 2019 / 6:23 am

    I think you look great in shorts. I would love to wear them more but I have a skin condition and I need to wear body makeup. Would anyone happen to know of a good one?

    • Julie
      July 21, 2019 / 3:11 pm

      Dermablend. I have used it to cover spider veins. Hope it helps.

  10. Eileen
    July 18, 2019 / 6:33 am

    I’ve gone back to dresses, for the heat. Simple, all cotton, one piece and go shirtdresses with sleeves if possible, much cooler.

  11. Mary
    July 18, 2019 / 6:36 am

    You look darling in shorts. Add them to your collection!

  12. Wendy
    July 18, 2019 / 6:52 am

    I enjoy reading your posts. The shorts look great on you. The island is beautiful hope you enjoyed your time in 🇨🇦 Canada.

  13. Angela
    July 18, 2019 / 8:06 am

    Great casual summer look on you! What size do you wear in the shorts?

    • Jennifer
      July 18, 2019 / 8:09 am

      I’m wearing a medium. They’re loose but comfy.

  14. Griselle
    July 18, 2019 / 8:19 am

    I think you look great! It is funny because we are the same age and I also stopped wearing shorts around the same age. This year I decided to order some just above the knee like yours and others just a little shorter. To my surprise I decided to keep all of them. I wear the ones like yours when I go out to summer activities and the ones that are a little shorter to use around the house.

    • Jennifer
      July 18, 2019 / 11:00 pm

      Thanks. We just need to keep an open mind and allow ourselves to experiment.

  15. Ellen
    July 18, 2019 / 8:30 am

    I am down to only bermuda length shorts now and the truth is, they just don’t feel like my best look and the proportions are always difficult. But I live in Texas and it is just so hot for a good chunk of the year. Sometimes they are just necessary for comfort. I want to be outdoors! A bit of self tanner, some attention to getting the proportions right and I just find peace with it. Same with swimsuits…I never feel I look great but I will be darned if I am going to pass on good times!

    • Jennifer
      July 18, 2019 / 10:59 pm

      I like your attitude Ellen.

  16. July 18, 2019 / 9:16 am

    You look great in shorts! Great earrings too!

  17. Jan
    July 18, 2019 / 9:38 am

    I think you look lovely in these shorts with your slim ankles showing. My husband uses a self tanner for his legs too before he will wear shorts. He keeps looking for a tanning lotion that has spf 50 or more included in the lotion. We live in Canada and can’t seem to find any. Do you know of one?

    • Jennifer
      July 18, 2019 / 10:58 pm

      I do not know of one so I let my self tanner dry for an hour then cover with sunscreen.

  18. Marce
    July 18, 2019 / 10:18 am

    First, you look great in those shorts! And thank you for the recommendation of the tanning lotion!!
    I have “translucent-type” skin resulting in many visible veins. When I was younger (and thinner) I didn’t really think about it, but sometime in my 30’s or so I began to feel self-conscious about it. I really super envied those people without this type of skin! Anyway, now in my mid-50’s, I am convinced that just having confidence in yourself in general, and not focusing on any self-identified flaw is the best way to enjoy life. Because I tend to be a person who gets cold easily, I really do not need the cooling benefit of shorts, but I admire people who confidently step out in tank tops or shorts no matter their circumstances or age and enjoy life!!

    • Jennifer
      July 18, 2019 / 10:55 pm

      Thank you, Marce. The wisdom and confidence we gain with age are priceless. They’re more than make up for the sore joints, wrinkled skin and age spots that come with them.

  19. Jayne
    July 18, 2019 / 10:38 am

    Hi Jennifer, I am a recent newcomer to your blog and I love it. I do not wear shorts either, although I do wear knee length skirts in summer. Seeing you look so good in shorts has inspired me to try them out at least around the house and in the garden to start with. I used to have decent legs, but at 76 they are no longer what they used to be.

    I live in Vancouver and have a daughter who lives on Vancouver Island. I hope you enjoy the rest of your trip in the beautiful area.

    • Jennifer
      July 18, 2019 / 10:52 pm

      Welcome, Jayne. My daughter lives in Vancouver too. Lucky you, it’s a gorgeous place to live.

  20. Freda Witt
    July 18, 2019 / 10:50 am

    I think you should wear whatever makes you comfortable. If you’re confident wearing it, you will look great. I am very fair skinned, and don’t tan, so I always wear a self tanner. I wear the same one you wear, but in med. To tan color. It looks natural and you can build up as much “tan” as you like.

  21. Katie
    July 18, 2019 / 10:58 am

    I can relate. I finally succumbed to shorts last summer because it was so hot and we were out on our sailboat. My legs have decades of sun damage from being a California beach baby…but I just didn’t care.
    Feel free to drop by for a sail on your way hone. We’re in Gig Harbor. Seriously!

    • Jennifer
      July 18, 2019 / 10:50 pm

      Thank you, Katie. That’s so kind of you.

    • Jennifer
      July 18, 2019 / 10:47 pm

      I like the Jergens Natural Glow Daily Moisturizer, in fair

  22. Penny
    July 18, 2019 / 3:27 pm

    I’ve never been a hat person, but have been trying to wear them more when out in the sun for protection. The first time I wore one I felt awkward, as it was definitely out of my comfort zone, and I felt silly wearing it. I like them on others, but never felt they looked good on myself. However, the more I got used to wearing one, the more comfortable I felt. I now have a few I have purchased and feel more at ease wearing them when walking my dogs, at the lake or out in the sun for any length of time.

    • Jennifer
      July 18, 2019 / 10:45 pm

      Good for you Penny! It just takes practice and they’re so smart to wear.

  23. Marlene Ward
    July 18, 2019 / 3:54 pm

    I really like the shorts on you and love white shorts in particular.

    I like to wear 7 or 9 inch lengths and maybe 1 inch narrower in the leg.

  24. Sherrye
    July 18, 2019 / 4:07 pm

    I’ve always worn shorts…I live in Georgia, where it can get pretty hot…up until the last couple of years. I stood on my feet at work for many years, and now have some vein discoloration around my ankle on one leg. I also have a couple of scars, one on each lower leg (one from the removal of a suspect spot on the leg). But, when we go to Florida I usually bring shorts and occasionally I’ll wear a pair out for a casual day. I actually prefer a length that hits between the heaviest part of my thigh and my knee. I’m not tall at 5’4″ and I find that to be a flattering length.

    • Jennifer
      July 18, 2019 / 10:44 pm

      Shorts, like skirts and dresses, always look best hemmed to stop at a spot where your leg narrows. These sound perfect for you.

  25. July 18, 2019 / 6:56 pm

    I just tried Jergens newest self-tanner, Wet Skin Moisturizer, to get rid of pasty white legs. You rub on while your skin is still wet from the shower, then pat dry. It does not transfer to towels or clothing, and gradually builds a nice glow within a few days. Much better than their other product, which I found can leave streaks. This is a winner, lots of positive experiences on Amazon reviews.

    • Jennifer
      July 18, 2019 / 10:42 pm

      Thanks for sharing Deanne. I will give it a try

  26. July 21, 2019 / 2:56 am

    Those white shorts look great on you and especially appropriate for being around the water and boats, but I think that length shorts would look nice on you in any casual setting. I like your earrings, too.

    I have heavy legs and never wear shorts or knee length dresses in public. I do wear shorts for gardening. Luckily, I have some nice, new, knee length shorts that I bought last year for gardening and never had a chance to wear yet. I am going to have to wear them in public when I go to the knee surgeon’s office next week. Having slacks touch my knee incision would be unbearable. As it is, the shorts will touch the top half of the incision. A long skirt would be a tripping hazard on our front steps. I am going to feel very overexposed in my shorts going through the busy hospital to the surgeon’s office next week.

    • Jennifer
      July 21, 2019 / 6:50 am

      Could you wear a below knee skirt?

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