Summer Wardrobe Essentials for a Casual Lifestyle Over 50

Summer Wardrobe Essentials for a Casual Lifestyle Over 50

With summer fast approaching I’m organizing the wardrobe essentials I’ll reach for again and again. I know that one woman’s wardrobe essential could be another woman’s not on your life because our needs are all unique. I’ll be sharing some of my essentials over the next few weeks and would love to hear what some of yours are.


A classic white tee tops my list. I wear them often throughout the year but during the summer they are a must-have for me. They’re a building block which I accessorize to create both casual and dressy looks.Jennifer Connolly of A Well Styled Life styling a classic white tee shirt

For a day of house hunting, I wore a crew neck version with a simple stretch skirt and topped it with a denim jacket. My finishing touches were a pink scarf, pink sandals, straw bag with pink handle and striped earrings with a pop of pink. Strategically placed pink dances the eye up my outfit and draws attention to my face where I am wearing pink lipstick.
Jennifer Connolly of A Well Styled Life wearing white tee and denim jacket

My white tee’s seldom last from one season to the next because sunscreen and deodorant discolor them. Because mine get replaced each year I don’t like to spend much for them but won’t wear cheap looking ones. I prefer opaque fabrics you can’t see through. Who wants to wear a cami in the hot weather? Not me.Jennifer Connolly of A Well Styled life wearing a classic white tee

I wear tanks under cardigans or jackets and short or 3/4 sleeve versions on their own. My neckline of choice is a vee to offset my broad shoulders but also wear crew and deep scoop necklines.

What is the one item you wear the most during the summer?

Thanks for readings ladies and have a great day!


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  1. May 21, 2018 / 4:35 am

    Very cute outfit. And spectacular bag!

    • May 21, 2018 / 7:12 am

      I love when it gets warm enough for me to bring that bag out. It’s a vintage favorite that I bought new 😉

  2. Pattie
    May 21, 2018 / 4:55 am

    I agree with the white tee being an essential, I have several with various necklines and sleeve lengths. I don’t want to wear a cami in the summer either so opaque is definitely the way to go. I love your blog and am interested in finding our your other essentials for summer wear

    • May 21, 2018 / 7:10 am

      Cami’s are just too much work in hot weather!

  3. May 21, 2018 / 4:58 am

    your skirt is too long

    • Deede
      May 21, 2018 / 5:10 am

      I think your outfit with the skirt is just spot on…I love the length and would say a shorter version would look frumpy…THX for including such great summer pieces…Hugs to you as always…Deede

      • May 21, 2018 / 7:27 am

        This skirt is an oldie with a folding waistband to adjust the length. Sometimes I wear it shorter or longer depending on my mood and if I’ve broken out the self tanner yet;) The angle these photos were taken from make it appear longer than it is #hazardoftallhusband

    • Melissa
      May 21, 2018 / 5:14 am

      Her skirt is perfect. I love it and would love to have one like it. It covers the widest part of the lower leg and just leaves elegant slim ankles showing. Unless you have stick insect legs that are also perfectly even in skin tone and not blotched with spider veins with a nice tan, then legs without stockings are much better as hidden as possible. This skirt does the job beautifully.

      • May 21, 2018 / 7:28 am

        This was a hide my legs day but be cooler than jeans;)

  4. May 21, 2018 / 5:02 am

    I like the pink you have added to this outfit, very sharp as an accent. White tees are also important in my summer closet, along with stripe tees. I found a great JCrew navy/whiteboard tee last winter and bought 2 because the fabric and fit are so good, I have a new one in reserve now for the next time I want a perfect shirt. I am wearing it casually with shorts and jeans but also to work with white jeans and a navy blazer.

    • May 21, 2018 / 7:17 am

      It sounds like a great shirt! You were so smart to buy two Deanne. I love striped tees too but realize I don’t have any. Must keep my eye open.

  5. Arlene
    May 21, 2018 / 5:06 am

    I find it really hard to find opaque t-shirts lately. Seems the sheer see-through fabric is all the rage.

    • May 21, 2018 / 7:18 am

      They do seem to be the rage and the organic ones seem to be the thinnest. Not what I like!

  6. Cindy
    May 21, 2018 / 5:13 am

    I really like this casual outfit. I have a jean jacket like this & love it!

    • May 21, 2018 / 7:29 am

      I reach for this denim jacket a lot! I love them.

  7. May 21, 2018 / 5:14 am

    That jacket hung in my closet for a few years. Last weekend in panic packing I grabbed it as a travel item. I wore it constantly….it was a WOW .Why didn’t I wear this before? I guess it was the “Boyfriend Blazer” thing I was doing at the time.
    My essentials for the summer/and all year are white and black long/elbow length and short sleeve Tees.I buy them on sale and always have a few unworn ones as go to(s).

    • May 21, 2018 / 7:52 am

      I love mine! I now have the white version too which will get worn more as the weather heats up.

    • Cheryl
      May 21, 2018 / 10:41 am

      So where do you buy your tees and what do you think is a reasonable price for a one-season shirt? I agree they don’t look quite as spiffy white carried over to next year.

  8. Melissa
    May 21, 2018 / 5:17 am

    I love to wear midi length dresses through summer with ‘bike short’ type underpants to stop the legs chafing and a lightweight jersey cardigan/wrap if I need something a bit warmer. I also like to brighten them up with a lovely light scarf.

    • May 21, 2018 / 7:32 am

      Bike shorts are a great idea for that! I don’t own enough summer dresses but will be adding some to my wardrobe this year. I wish more had sleeves but the cardi’s are a perfect solution.

    • Margot
      May 22, 2018 / 6:15 am

      There are also products that apply like stick deodorant to prevent chafing if you don’t want to wear an additional layer. I found mine at Walgreens (by the first aid products?).

  9. Linda Lennon
    May 21, 2018 / 5:43 am

    Love that handbag! I just tossed several v-neck tees from last year and beyond and I have been searching for the right ones for a replacement. Not so easy! Your skirt is great. Love skirts in the summer. My problem is always shoes; I need something with support but they need to be able to withstand a lot of walking. I always prefer sandals when I have a good pedicure. You are my inspiration for my move to Palm Desert! I actually gave away my assorted 6 winter coats this weekend; big release for me! And I have to say it was not easy!!

    • May 21, 2018 / 7:35 am

      You must be getting excited about your move. Palm Springs is so fabulous I bet you love it!! Good for you for uncluttering your wardrobe before the move!

  10. Kathleen
    May 21, 2018 / 7:10 am

    I love this outfit. A pair of capris would work nicely too.
    My go-to for summer is a three quarter sleeve boat neck tee. I love white or pink. Paired with jeans or capris and a necklace or bangle.

    • May 21, 2018 / 7:37 am

      I love 3/4 sleeve tees in a light weight too. They’re perfect for showcasing bracelets!

  11. May 21, 2018 / 7:21 am

    I agree skirt is a bit too long…but I love the out fit…well put together….I have several black and white tennis skirts that I wear in summertime and the chicos black traveling slacks are a must have for me….

    • May 21, 2018 / 7:40 am

      I’m not sure my knees are short skirt friendly these days. I haven’t tried the traveling slacks. Is there something special about the fabrication?

      • Risa
        May 21, 2018 / 5:34 pm

        I think Mary is referring to Chico’s Travelers line of clothing. The NoTummy slacks are a great weight for warm weather, with the added advantage of being non-wrinkle.

        • May 21, 2018 / 9:18 pm

          Thanks Risa

  12. Susan
    May 21, 2018 / 7:38 am

    THANK YOU for saying that you replace your white tees every year! A sparkling white tee is well worth the $10 each year. I’ve been trying to make mine last longer, and just end up feeling grubby. I’m a newcomer to the Karen Scott brand, and really like the thickness of their knits. Some cute prints too. Though they’re not always available, Costco’s Kirkland brand sometimes has a great V-neck white tee for about $10. Grab one to try while you’re buying your salmon and paper towels — it’s returnable if it doesn’t fit, and a terrific value if it does. Other summer essentials: OPAQUE white ankle pants or capris (why are they all so see-through?), pale gray capris, skinny lightweight denim mid-calf length jeans, a Breton striped black and white tee, a mid-calf print knit dress for the hottest weather (print hides the wrinkles, and a dress is the coolest option there is), and a casual-but-nice long dress for summer restaurant evenings.

    • May 21, 2018 / 7:43 am

      I will grab one next time I’m in Costco, thanks for the heads up! Opaque white pants are that elusive perfect piece I’m always thrilled to find. Especially if I can get them in linen. I do agree about prints and wrinkles. Summer friendly too

  13. Valorie
    May 21, 2018 / 9:01 am

    Ladies, ladies, ladies!!! Nowhere did Jennifer as you to critique or criticize any portion of her outfit! How can you possibly think that is ok? Say something nice, share about your summer essentials as she asked or SAY NOTHING!

    • May 21, 2018 / 9:34 am

      Thanks for your your friendly, insightful reminder Valorie! I often point out what doesn’t work on my body which I assume encourages ladies to share their opinion of my outfit.I certainly don’t expect everyone to like my choices.

  14. Viv Butler
    May 21, 2018 / 9:25 am

    Love the simplicity, so chic.

  15. dale duckworth
    May 21, 2018 / 10:55 am

    I find Lands End t shirts to be a good buy. Great fabric and fit, good price. I like the cotton with a little bit of stretch.

  16. Shannon
    May 21, 2018 / 11:03 am

    Love your outfit! I was never a pink girl but for some reason love it now. My husband tells me it’s not a good color for me as I’m blonde and fair so love the idea of pink accents, so girly and pretty:)

    • May 21, 2018 / 9:32 pm

      I didn’t wear pink for many years but am embracing it fully now. I would think it would be very flattering on a fair-haired blonde. Just sayin’…

  17. Kathleen O'Brien
    May 21, 2018 / 12:18 pm

    Oh my goodness! I’m with you on new white tees every season. I also do that with my summer black ones as well. They are such workhorses they need replacing to look nice. And like has been said, they must be opaque – what is with all the sheer ones?? I’m also weird, I guess, because I like a longish sleeve as a lot of those so called “short sleeves” hit me right at the biggest part of my arm – not a nice look. So I often look for elbow or 3/4 lenght. Hard to find for us fluffier ladies.
    I’m also looking for a longer, fuller guacho or colutte, as mine finally are so sad they gotta go. I can’t wear things too short on the legs (capris shorts skirts) as my prominent scars from multiple operations on my knees are very obvious and no one wants to wear opaque tights in the summer. Any ideas on wear to find those in a 2X – maybe I should make them?? And another must have is my shortelette underware by Undersummers – not a foundation or squeezy – but longer lenght legs that eliminate chaffing. So light and comfortable you forget they are there! Perfect under dresses and skirts.

    • May 21, 2018 / 9:35 pm

      I have not seen longer gaucho’s but always loved the look. They will come back in style, everything does but if you sew, go for it!! I agree that short sleeves can be very tricky because the widen the arm wherever they stop

  18. Julie Anne
    May 21, 2018 / 1:20 pm

    Black tees. I gave up on white. My tinted sunscreeen was forever ending up on them. Our water is hard so doesn’t clean up whites well. Last year I bought a black one (George) at Walmart. It washed well so I bought several more. In the winter I wear them under blazers, in the summer they’re under various lightweight blouses. I don’t want the sun on my arms and know I’m at the age not to display them.

    Every summer I’ve been in search to the perfect lightweight black skirt. No luck yet. I even tried skorts and hated them. No shorts for me. I hate sitting on a chair and ending up almost ripping my skin off when I stand up.

    My other staple is dresses. Sleeveless and worn with a shirt as a jacket.

    • May 21, 2018 / 9:30 pm

      Great point about the tinted sunscreen. I only wear the tinted sunscreen on my face but it still can get on the color of my white shirts. You just reminded me of one reason I dislike shorts;)

  19. May 21, 2018 / 2:35 pm

    I white tee has always been front and center in my closet, year round. You can wear it with everything from a ballgown skirt to jeans. I’m gravitating back to dresses, but not as short as when I was younger. My favs are midis. xoxox, Brenda

    • May 21, 2018 / 9:28 pm

      Dresses are on my radar this summer too! Quite versatile and very cool in hot weather.

  20. Lori
    May 21, 2018 / 3:18 pm

    I love a white tee and a lightweight black one. I can never seem to find a denim jacket that works on me, and I can wear ONLY mid or lower calf length skirts.I have not been able to wear shorter skirts, dresses or shorts since i was 26 years old. I envy ladies who do not have gnarly varicose veins or a zillion spider veins on their legs. Think about other people’s challenges before you criticize their choices, people.

    • May 21, 2018 / 9:27 pm

      My mom suffered from very gnarly, painful varicose veins which were miserable for her. Have you tried self-tanner to help camouflage them a bit?

  21. Amelia
    May 21, 2018 / 3:45 pm

    I love that the black skirt is adjustable and can be worn short or long. Very creative to add the pink accents. Love the style and color of the shoes. You look very lovely. I wear lots of dresses and skirts in the summer. White pants, pedal pushers in all different shades are paired with my collection of white, cream, and lightweight navy and black tee shirts. I’m always on the look out for good quality quarter sleeves tee shirts. Linens are featured in my summer wardrobe but limited to one item per outfit. I haven’t fully embraced the all over wrinkles effect of this beautiful and comfortable fiber. Thank you Jennifer. ~Amelia

    • May 21, 2018 / 9:25 pm

      Your essentials sound lovely Amelia. I wish I looked better in pedal pushers. They’re such a great middle of the road answer.

  22. Kristine Birkholz
    May 21, 2018 / 4:21 pm

    I just love your classy outfits, Jennifer. What is your feeling about women wearing shorts when they no longer have youthful-looking knees? I’m nearing 59 years old and won’t wear Capris because I think they look frumpy on most women, so I wear walking shorts. I’ve seen a lot worse than older-looking knees, but what do you think?

    • May 21, 2018 / 9:23 pm

      My knees are wrinkling like an elephant but that’s life. I just bought a pair of long shorts for pickleball and will be slathering on the self-tanner to help offset the wrinkles. If the weather is hot and the activity calls for shorts, I think we should go for it.

    • May 22, 2018 / 2:53 am

      I am the same age, Kristine. I do not like the look of capris, usually, because they really seem to cut us off. When I do choose them, I wear the fitted ones with a looser top. I also tend towards the walking shorts. Since I am short-5-1″, they hit me right at my knee and cover the wrinkles. Ahh-so sad. I still have nicely shaped legs but hate the saggy skin. White white white for summer! Jennifer, please continue to wear what makes you feel good about yourself. You never said every woman should wear it. Just offering suggestions. I give you kudos for blogging. I couldn’t handle the haters and naysayers. . Some people squash others to make themselves rise up. “Keep on keeping on!’

      • May 22, 2018 / 7:19 am

        Thanks for your support Lizzie. Social media has given everyone a forum to speak which makes the landscape a bit rocky at times. My goal is to share what I know and do with the hope it inspires other women to dress with confidence.

  23. May 21, 2018 / 4:45 pm

    You look awesome in this outfit, Jennifer. I love white tee shirts and have several versions. My favorite here though are your shoes…love them! This whole look is stepped up casual in a big way.

    • May 21, 2018 / 9:19 pm

      Thanks Pam, they are surprisingly comfy

  24. May 21, 2018 / 9:00 pm

    How cute! Yes, Jennifer, we can still look cute at our age, n’est-ce pas? I love the way you have put this outfit together adding that all important pop of a third color (pink). Basically, these are all staples that should be in every well-dressed woman’s wardrobe. Where would we be without the LWT (little white tee)? I love the shoes. Every time I put on a shoe tied around my ankles I feel as if I should go on point. Trust me, they look much more comfortable than point shoes tied tightly around your ankles. Just had a ballet flashback!

    The bag is also adorable. Nothing says summer like a great straw bag.

    • May 21, 2018 / 11:46 pm

      I agree!! I always look forward to bringing out my wicker and straw handbags. I remember tie shoes very well and have the bad feet to show for it!

  25. Eileen
    May 22, 2018 / 3:53 am

    My favorite white tee is the boat neck with 3/4 sleeve, plain and striped ( since I have a pear shape and small shoulders). Light blue tops are another cool favorite for me. Lately I have been wearing white cotton poplin button down shirts with the sleeves rolled up, some times I size up for some air flow. And any cotton blouse with sleeves I try to snap up, I don’t care if I have to iron, I just feel cooler in them. And my favorite pants are cotton poplin, pique, or seersucker ending at the ankle, or a loose wider linen pant. The longer pants work better when sitting. I am not a fan of pants cutting me off at mid leg, I have larger calves, so no mid length dresses either. Walking shorts, skirts and dresses are all useful, it just depends on the style and fabrication. The hardest thing for me is finding quality cotton, rayon and linen, I just returned from France, and their fabrics are much better than our selection, and there was less polyester, ( not my first choice in the heat), and their linen clothes were much nicer. Jennifer, I love your pink shoes and bag, fabulous!

    • May 22, 2018 / 7:27 am

      I’m not a fan of polyester in the summer. It’s doesn’t breathe. Looking forward to hearing all about your trip!

  26. Linda
    May 22, 2018 / 4:10 am

    Love, love, love your outfit!

  27. Margot
    May 22, 2018 / 6:24 am

    I am a sucker for a white shirt and have them in many variations. The basics get replaced yearly but I hang onto the ones with unique details as long as I can! I also love denim jackets as they seem to go almost everywhere my casual life takes me. I have a roomy distressed one that I wear over thicker sweaters in the fall and early spring, a dark wash from J.Jill that has a little Lycra in it and is so comfortable, and a white one I break out for summer.

    • May 22, 2018 / 7:37 am

      I need a roomier one for sweaters, thanks for the idea Margot. I just love denim jackets!

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