In a Pickle: What to Wear

Living in an active retirement community feels like summer camp for adults. There’s a class, sport or club meeting happening all day and evening. I hate to think I have a totally inappropriate wardrobe for this new lifestyle, but I’m beginning to wonder. We all know that activity appropriate wardrobe choices are a smart idea. Notice how delicately I put that? They also have to be true to your own style.

I’ve tried a few new activities recently that I was unfamiliar with and didn’t know the dress code so chose from my existing wardrobe.

We decided at the last moment to attend a pickleball orientation and lesson. It was hot and sunny with no shade. Since I don’t own shorts I wore skinny pull-on jeans, a three-quarter sleeve T-shirt, black sneakers and a white cotton hat. I knew the jeans were a bad idea but I didn’t have an alternative. Not only did I look out of place, I was physically miserable and roasted. Most women wore long tennis skirts with a tank top and visor. I’ll keep my hat over a visor because I prefer extra sun protection. I haven’t tried on a tennis skirt in over 30 years but will check them out to see if they feel like my style because pickleball is a hoot. Jennifer Connolly of A Well Styled Life wearing ECCO Soft 7 Cap Toe sneaker

I tried table tennis last night and it was a blast. I wore the new white sneakers I purchased for pickleball, black jeans, and a white shirt. Most women were wearing a cotton tee with lightweight pants or workout clothes. It was much more aerobic than I anticipated so I was very hot. I need more athletic garments for this lifestyle that are made to move and be perspired in. Jennifer Connolly of A Well Styled Life wearing ECCO Soft 7 Cap Toe sneakers

So far I have added 2 pairs of athletic shoes to my wardrobe and plan to try some new options on over the weekend.

Have you shown up for an event dressed totally improperly?

Thanks for reading ladies and have a great day!


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  1. Janet
    May 17, 2018 / 3:47 am

    I may dress a little differently but not inappropriately. Having said that, I probably would have done the same as you because my wardrobe wouldn’t have fit that new lifestyle at all. That would an extreme change for me both in climate and activities! I am curious about what you bought but I’m sure you will do it with style!

    • Jennifer
      May 17, 2018 / 7:18 am

      It’s going to be fun trying new looks for this more active lifestyle!

  2. Linda
    May 17, 2018 / 4:27 am

    I am loving your posts about this new phase of your life! Please keep letting us know how things are going because many of us will be living in senior living villages in the future and it’s helps us all to prepare! How is the food there and what are the people like? How far away are stored and medical facilities? Does your dog like it? Do they have groomers? Was every aspect of your life thought out by this place?

    • Jennifer
      May 17, 2018 / 7:20 am

      They do have a nice restaurant and cute sandwich shop. For other food and dog facilities it’s just a 15 minute drive. Everyone is friendly and most seem quite active. I’ll keep everyone posted!

  3. Kathleen
    May 17, 2018 / 4:48 am

    I’m enjoying reading about your new life too. I’m thinking if you haven’t tried on a tennis skirt in 30 years it’s probably been the same for Bermuda shorts. They’re as long as a skirt and I think you could hold onto your style and perhaps be more comfortable with them. My two cents. Now I’m about to google pickle ball

    • Jennifer
      May 17, 2018 / 7:28 am

      I will be trying both on soon. I’m also thinking an athletic dress with bike shorts or a skort, if they still exist.

      • Lis
        May 17, 2018 / 10:59 am

        Try Lilly Pulitzer skorts. I work out in them and they are active wear.

        • Jennifer
          May 17, 2018 / 9:51 pm

          Thanks for the tip!

      • Susan
        May 17, 2018 / 11:17 am

        skorts do exist! I have found them at macy’s and they are cute and comfortable. I don’t know about pickleball, that’s pretty active. I attend an exercise class three times a week and sometime yoga on other days. thank God no outfit judges and we just wear whatever can be sweated in–exercise capris, tanks, yoga pants, t-shirts, headbands, etc.

        • Jennifer
          May 17, 2018 / 9:52 pm

          Outfit judges have too much time in their hands Susan. I’m shooting for comfortable clothes that fit my style and lifestyle.

  4. May 17, 2018 / 4:55 am

    Good to hear from you Jennifer and kudos for trying some new activities! You may need to shop for some more active clothing. A few ideas for you.
    If you can observe some of these before you participate you might have a better idea how much you will need to move so you can be more comfortable. I am a big fan of Zella activewear at Nordstrom, and you have great legs so you might try leggings instead of shorts in lighter weights and mid-calf lengths. I wear them all summer for barre classand they are not hot. Knee length shorts would also be a good option, really no more leg exposure than wearing a skirt. And a summery floaty skirt would also be an option for some activities. We look forward to more reports on your new adventures!

    • Jennifer
      May 17, 2018 / 7:30 am

      I’m glad to be back! I missed you all. You’re right about shorts not showing much more leg than a skirt. I think fabrication and color will be very critical. I’ll check out Zella. I’ve never heard of them before.

    • Margot
      May 18, 2018 / 7:44 am

      Capri length leggings are great too – as long as my top covers my rear!

  5. May 17, 2018 / 4:58 am

    Honey, you need some shorts! I don’t think you should worry about how you look in them! When it is hot you should wear shorts! I live in Florida and older than you and I always wear shorts in the summer. Many shorts hit at the knee. They would look great on you!

    • Jennifer
      May 17, 2018 / 9:53 pm

      I will be checking them out now!!

  6. Susan
    May 17, 2018 / 5:21 am

    I suggest you try golf skorts! I find them more comfortable & cooler than shorts. And the fabrics now are great-comfortable in hot weather, lots of cute styles & cuts, many are pull-on styles. Golf skorts are about 19″, a couple inches longer than tennis skirts. You don’t have to wear “golf shirts” with them-they look cute with all kinds of tops. And you need a hat! Plenty of cool, nice looking ones out there. I’m not a fan of visors, either. Your hair will not be up to keeping that sun from your face & ears!

    • Jennifer
      May 18, 2018 / 6:41 am

      thanks Susan! I’ll check them out

  7. Rose Leewright
    May 17, 2018 / 5:41 am

    Please be careful on the Pickle ball court. I agree it is a really FUN game but make sure you are using the correct court shoes. I did not and my pickle ball playing days are behind me, after a broken shoulder in two places and stiches in my head ☹️. So now I just focus on golf with 2 feet on the ground ????. Hope your community is as much fun as I have found mine!

    • Jennifer
      May 18, 2018 / 6:43 am

      Oh wow Rose I’m so sorry to hear that!! I just bought some tennis shoes with soles that slide. What kind were you wearing? I hope you’re recovered.

  8. Kim
    May 17, 2018 / 6:00 am

    Jennifer, I think you might really enjoy either knee length/bermuda shorts or a skort for your activities. I like both of these as long as they’re made of a fabric meant for athletic wear and with some stretch to them. Eddie Bauer and Athleta have some good options. I live in a hot climate and live in these for 8-9 months of the year. I’m in my 50s. I’m so glad you’re getting involved in your new community and trying new things.

    • Jennifer
      May 17, 2018 / 9:55 pm

      I just tried on some shirts today but they had no more give than the jeans I wear. My next stop is where they sell athletic wear! I need the right fabrics.

  9. Téa
    May 17, 2018 / 6:01 am

    I like the “All Day Skort” from Athleta and the running skort by “Skirt Sports”…I like my clothing to have SPF…check out the fun ICKULS brand shirts, too…golf skorts are usually longer than tennis skorts, FYI…also, Lands End has fun SPF tops. I know you’ll figure it out. PS – my “athletic wardrobe” is very strategic…all the colors coordinate. I steer clear of “outfits” and buy “pieces” that all go together.

    • Jennifer
      May 17, 2018 / 9:56 pm

      Thanks for these tips! I’m anxious to try on some skorts! They sound right up my alley.

  10. Jayne
    May 17, 2018 / 6:02 am

    We love Pickle Ball! It’s good for the body and the brain as there is much strategy to the game. It’s a great way to get exercise and meet fun people. Enjoy it! You always look great, but I agree with the other comments that you could really rock some light weight knee or mid calf length leggings. Skorts also work great for Pickle Ball and other activities. You’ll have fun adding a new dimension to your wardrobe. We can’t wait for your reports!

    • Jennifer
      May 18, 2018 / 6:45 am

      I’m so new to this it’ll be awhile before I get to the strategy part:). Right now it’s just about getting a volly going. It is fun

  11. Eileen
    May 17, 2018 / 6:09 am

    Coming from the foggy Bay Area to Sacramento heat was a shock for me also, so I’m sorry I am laughing , I was in the same predicament. ???? My skin can’t take that much sun either, so I was scrambling for hats, and white clothes pretty fast! Returning from Paris in about 5 days, I’m going to miss the cool weather here. And the fashionable people , and wonderful food. ????????????‍????????

    • Jennifer
      May 17, 2018 / 10:05 pm

      It’s quite the adjustment for sure! Your trip sounds wonderful

  12. Cheryl Ann
    May 17, 2018 / 6:14 am

    I totally understand, since athletic has never been in my definition of myself! Now I do Tai Chi and struggle with clothing choices. Can’t wait to see where you go with this…and glad you had fun. Blessings, my friend…

    • Jennifer
      May 17, 2018 / 10:06 pm

      Thanks so much Cheryl Ann! Xx

  13. Heidi Trotta
    May 17, 2018 / 6:17 am

    I’m very interested in what you will be purchasing. I’m going to be in the same spot myself.

    • Jennifer
      May 18, 2018 / 6:45 am

      I’ll keep you posted

  14. Laurel
    May 17, 2018 / 6:24 am

    I have those sneakers in baby blue and love them! So comfy and cute. And sneakers are everywhere! I’ve had good luck with athleisure clothes from the T by Talbots line. Also Zella at Nordstrom. Good luck and enjoy the new activities. They sound great!

    • Jennifer
      May 17, 2018 / 10:07 pm

      I haven’t heard of T by Talbots. Thanks for the tip I will check them out.

  15. Lori
    May 17, 2018 / 6:37 am

    Try SPF clothing from Coolibar. They are online only. Very cute and comfy!

    • Jennifer
      May 17, 2018 / 10:08 pm

      I have lots of hats and cardigans from Coolibar. Now I’ll be checking out their clothes too. Great idea. Thanks.

  16. Heather
    May 17, 2018 / 6:41 am

    I’m going to second several of the comments. You should try shorts and crop leggings. Once I retired and got a dog, my lifestyle changed. I was convinced I couldn’t wear shorts but it’s amazing how they’ve changed. Lots of stretch in many of them and they hit me right at the knee. Leggings were something else I was sure weren’t appropriate for me but if they’re worn with a longer top that covers the bum, they work for us. Have fun with your new lifestyle and the new wardrobe to go with it!

    • Jennifer
      May 18, 2018 / 6:46 am

      Thank you Heather. This is a new world for me

  17. Mary McCoy
    May 17, 2018 / 6:44 am

    Pickleball is so fun! If you don’t want to wear shorts, try wearing some yoga pants or leggings. Target has great yoga pants for good prices and also Old Navy does too. They also have great Tshirt type yoga tops that are super comfortable to play pickleball in, and non-constricting.

    • Jennifer
      May 17, 2018 / 7:16 am

      Pickleball is a blast! I love Target so will check them out. Thanks Mary!

  18. Cathy
    May 17, 2018 / 6:50 am

    Since I live in the south my summer wardrobe consists of capris, cotton tees, shorts (Bermuda), and tanks. I’ve wear Capri leggings and a tank for workouts. My favorite shoes are sketchers and ryka walking shoes. Humidity is a killer here.

    • Jennifer
      May 17, 2018 / 7:14 am

      Humidity does make the heat worse so I’m lucky it’s at least dry here!

  19. Clarissa C
    May 17, 2018 / 6:52 am

    Jennifer, I understand! I live in Arizona and comfortable summer dressing for an active lifestyle takes a lot of trial and error, especially if one is not all that thrilled about shorts. I have good legs, but after multiple attempts at expensive laser and saline therapies, have decided that the spider and varicose veins will pop out faster than I can ever zap them. I avoid shorts now and opt for lightweight breezy linen pants, pull-ones like Michael Stars offers. I buy them from Nordstrom, Garnet Hill, EBay and have a lot since after one wearing they must go into the laundry. If you do want to try a good Bermuda short, I like the Jag Ainsley pull-on; it is one the few with length and a close fit on the thigh
    ( thereby avoiding that billowy British officer in the tropics look) . And in keeping with the comments above, the Zella line at Nordstrom is great! There are many pickle ball enthusiasts here and many wear knee length sports/ yoga capris. I have a chic and sporty friend in our age cohort finds some pretty cool stuff at Chico’s too! Reading your comments about roasting in jeans and perhaps feeling a bit overdressed made me laugh and brought back memories about adapting down here. I have switched out Hermès scarves tied in jaunty styles for Madewell voile bandanas. Keep us posted????

    • Jennifer
      May 17, 2018 / 7:13 am

      These are some great suggestions. Thank you Clarissa! I particular dislike that British officer looking short which may be part of why I stopped wearing them. They’re too preppy looking for my style.

  20. Linda Lennon
    May 17, 2018 / 6:58 am

    I am moving from NY to Palm Desert, CA in another month and will be in a similar situation except that I have been pretty active my whole life. My go-to for golf, hiking, etc. is the skort. I have basic ones from Athleta and some cute printed ones from Talbots. Also I like the long sleeve sun shirts from Lands End – I own 2 white ones and several stripes & prints. Chico’s also has a line of golf wear that doubles as activewear. I like Wallaroo’s for some cute sun hats.

    • Jennifer
      May 17, 2018 / 7:01 am

      Good luck on your move! Yes the big change is in my athletic level which is good for me. Thanks for these suggestions.

  21. Gail Schwartz
    May 17, 2018 / 7:12 am

    Don’t be afraid to wear Bermuda shorts. I dress them up and down in hot weather. I’m 70 and still want to look good! Active woman need special clothing for their activities, so you have to change how you look in the mirror. You will still get a chance to dress up a little for events in your community. No one will look as good as you!

    • Jennifer
      May 17, 2018 / 10:10 pm

      I’ve never been this active so I’m working my way into it. Thanks for your kind comment Gail!

    • Jennifer
      May 18, 2018 / 9:30 am

      These look terrific. I am going to try them on! Thanks Dale

  22. dale duckworth
    May 17, 2018 / 8:37 am

    Ha, not the Sumatra Macy’s! Summer.

  23. May 17, 2018 / 8:44 am

    Jennifer I am a little older than you and I still wear walking shorts and the best ones I find are “Lissette” shorts. They are comfortable, pull-on style , plus the material is soft. They come to the knees.

    • Jennifer
      May 18, 2018 / 9:27 am

      I love Lisette pants but didn’t know they made shorts! Thanks so much, I will look for them.

  24. May 17, 2018 / 9:08 am

    Jennifer, you have fantastic taste and it is going to be exciting to watch you transition into active wear. Before you know it you’ll have your wardrobe right where you are comfortable and on trend!
    Believe me, I know the challenge of staying cool and comfortable durning Florida summers and fall. What to wear when you are melting? I’ll be looking to you for some fresh inspiration.

    • Jennifer
      May 18, 2018 / 9:25 am

      Thanks Rosemary! I’m glad this is dry heat because it’s not quite as brutal as yours is in Florida. Being the new kid on the block is an interesting experience…especially when the block is so different from your old one.

  25. Carlene
    May 17, 2018 / 9:12 am

    I recently moved to a golf community and experienced a similar wardrobe issue. As it turns out, the right answer here is golfwear all day every day. I have come to love skorts and SPF protective polo shirts. Check out golf brands such as Jofit, Nivo, Tail, Sansoleil, Golftini and Adidas. Good luck!

    • Jennifer
      May 18, 2018 / 9:24 am

      Thanks Carlene! Sun protection is always at the top of my list too.

  26. Ann
    May 17, 2018 / 10:19 am

    What about a skort

  27. retro-roost
    May 17, 2018 / 10:58 am

    I recently moved to an active community, and notice that women wear athletic-oriented stretch pants (leggings) with modern sneakers, and attractive appropriate tops — brightly colored and well-styled sweatshirts, hoodies, tees, etc. Many wear this clothing for in-town errands, and it looks comfortable and pretty. It also includes jewelry! I see little denim (which I typically wear for casual days, but probably for not much longer as I’m working to transition my style). I also am soooooo ready to thin my closet of corporate-style attire. Yay!!

    • Jennifer
      May 17, 2018 / 10:12 pm

      That’s similar to what I’m seeing here. Most everyone wears sneakers everyday.! It’s certsinly a different world than I used to live in.

  28. Jan
    May 17, 2018 / 11:47 am

    Check out Atheta for quality options. I love their pants and skort type skirts. I wear them for all daytime activities.

    • Jennifer
      May 17, 2018 / 10:13 pm

      Will do. Thank you

  29. Amelia
    May 17, 2018 / 12:09 pm

    Hi Jennifer, this is my first time commenting and glad I’ve finally mustered up the courage to do it. Living in an Active Retirement Community is really peaking my interest. In my mid 60’s and retired three years, my husband retired five years ago. Our home and yards …about an acre and a half are starting to make us rethink what we want to do in our retirement years. As dearly as we love our home and the space, we don’t want to be beholden to maintaining both as we aged. Active Retirement Community living had crossed our minds more than once. Also a reader of your blog for a while now, there’s no doubt in my mind you will find a very stylish way to fit in with the group activities going on in your new home. I’m reading your blog with interest on how your feel about living in an Active Retirement Community. Hubby and I are mulling over the next step of our retirement saga. Thank you. Amelia

    • Jennifer
      May 18, 2018 / 9:23 am

      It’s a tough decision Amelia which is why we decided to rent for a year to see if we like it. So many of us are at the same stage so I am happy to explore and share with you. Good luck and thanks for reading.

  30. Deede
    May 17, 2018 / 3:12 pm

    Jennifer, Sending you big hugs as you make such a huge effort to try out these new things…If all else fails and you feel miserable, may I suggest going home, getting a great book and a symphony bar…preferable nuts variety…and locking your door…Deede

    • Jennifer
      May 17, 2018 / 10:14 pm

      lol! You’ve read my mind Deede!! Bless you xox

  31. Renee
    May 17, 2018 / 4:11 pm

    Hi Jennifer,
    Try the Loft! They have great Bermuda shorts with different lengths, colors and I love the thickness of fabric (can’t see through them) that I wear. I’m 61, if I can wear them you can, too :). I think you’ll look great in them!! I live 40 miles inland of San Francisco…where it gets HOT!!!

    • Jennifer
      May 17, 2018 / 10:15 pm

      It sounds like we are not too far from each other. I hadn’t thought of Loft! Their prices are so wonderful. Thanks for the tip!

  32. Karen
    May 17, 2018 / 7:35 pm

    I like sport skorts like Athleta, Eddie Bauer, Orvis, Nike and many other brands. I wear them for golf, hiking and around town, older legs be darned . They come in so many different lengths and can be worn at the waist or slightly below. They’re cool, have pockets, and can be easier to shop for because shorts can look frumpy if they don’t have just the right taper. Good luck!

    • Jennifer
      May 17, 2018 / 10:17 pm

      You’re so right about shorts. With my flat backside and narrow hips I expect a skort will be much easier to get a good fit than a short.

  33. May 17, 2018 / 9:41 pm

    Coolibar has a variety of casual, sporty clothes that might work for you! Love reading about your new adventures…K

  34. May 18, 2018 / 3:11 am

    The women where I live wear nothing but yoga gear. Whenever I dress, they ask “where are you going dressed so fancy!” It used to bug me but now I just do what I do. The activities sound great! Glad you are settling in.

  35. Sharon
    May 18, 2018 / 7:18 am

    Hi Jennifer. For pickleball, make sure you are wearing “court” shoes, which are wider across the ball of the foot for stability. Otherwise you are at risk of a painful sprained ankle (ask me how I know). And be sure they have “non-marking” soles in case you ever play pickleball on an indoors court. Personally, I wear breathable leggings that end just below the knee (I don’t look as good as I used to in those short tennis skirts and my knees seem to have gotten baggy in the last few years–how did that happen???). Have fun with pickleball! I agree with you — it is a hoot!

    • Jennifer
      May 18, 2018 / 9:20 am

      Thank you, Sharon!! I will check to be sure mine have the right sole. My knees are sagging too…everything is;)

  36. Kathy
    May 18, 2018 / 3:38 pm

    Hi Jennifer, I discovered your blog a couple of months and your story is intriguing me. A little over a year ago my husband retired and after 14 corporate moves we returned to our college home town. The climate and our life style is completely different from what we’ve know for the past 10 years; so for the most part I feel like I’m undergoing an several transitions. And on top of all of that, I’m evaluating if I’m ready to stop coloring my hair and accept the gray. I think I am, just not so sure if my friends are.

    My parents lived in a Del Web community in Northern California until this past summer. They were there for over 15 years and loved every minute it. There are so many wonderful activities and services just outside your front door, I hope it works for you and your husband.

    • Jennifer
      May 18, 2018 / 8:29 pm

      Welcome Kathy! Active retirement communities are an interesting option for us.

  37. Kathy
    May 18, 2018 / 3:39 pm

    Incidentally, I LOVE your eye glass frames! So cute and flattering!

  38. Bonna Nichols
    May 19, 2018 / 8:00 am

    I have nothing to add that hasn’t been said except, be true to yourself! You know what works and what doesn’t.

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