A Classy Way to Wear Shorts This Summer - Elegantly Dressed and Stylish
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A Classy Way to Wear Shorts This Summer


Not sure how to style a pair of tailored shorts? I am sharing how I styled mine today.

tailored shorts, espadrilles and white blouse

A Classy Way to Wear Shorts this Summer

Have you tried styling shorts   in a classy way? Do you have a routine of wearing your shorts the same way, with a similar tee shirt and sneakers each time you put it on?

These shorts, from Tarshay, are very versatile and I have been wearing them on repeat this summer.  I have really been enjoying more tailored looks this year, and these shorts can be dressed up a bit, as I have shown here. Here is another Target option that I love.

Now I know, I do mostly prefer summer dresses as they are away from the body, and don’t cling in the summer heat. Well, these shorts, with the A-line shape provide a similar feeling, although structured. The leg opening is wider, therefore roomier, if you don’t want to try slim fitting Bermudas. They keep you cool and have a bit of stretch. I am wearing my usual size 4 in these.

You have seen me style them HERE, in a more casual vein, with a minimalist vibe.

A textured white top ( this one is from Mango) brightens the look and keeps the neutral feel.

I tend to keep jewelry simple in the Summer, and sometimes opt for a silk scarf instead of a necklace.

Another option besides a fitted tank, or a white blouse, would be to add a linen blazer with a cami or tank. I love the look of a shorts and blazer look that has been quite popular over the past several seasons.

This belt, is one of my favorites from Mango a few seasons ago, and is worn instead of the cloth belt that comes with the short. It adds texture and color to the neutral look with the woven and wood texture. It just elevates the look!

Life Lately

I didn’t get to post Friday, as the 8th was my Birthday. Yes. 54 years! Where has time gone?

I had a lovely birthday dinner at this Italian Tapas restaurant, Cicchettis in Uptown.  Chicken meatballs with rosemary, ricotta and tomato sauce was oh so good! Mom had a shrimp and pollenta dish, and hubby got his oysters. We also shared some bruchetta with sun dried tomatoes and ricotta. We enjoyed a bottle of Calfornia wine from Paso Robles, which is a wine region more and more familiar.

Hubby surprised me with roses, a cake and Godiva, and money I received will go to bringing back a souvenir from Italy. ( bag or shoes?) 🙂 It was a lovely time!

tailored shorts, espadrilles and white blouse

tailored shorts, woven belt and white blouse

tailored shorts, espadrilles and white blouse

Do you enjoy wearing tailored shorts? I’d love to hear how you style them. Tell me in the comments.


Tailored shorts– Tarshay

top- Mango ( Similar option)

Andre Assous espadrilles

Belt- Mango ( old)   option ( similar option

leather clutch JJ Winters-

Prada sunglasses

Join me tomorrow for Turning Heads Tuesday!

Jess xx


  • Nancy Weiss
    Posted at 14:06h, 18 July Reply

    Happy Birthday!!! Great ideas as you can’t go wrong with a white blouse. And thank you for showing me how to wrap a belt that’s a bit large too.

    • Jess Jannenga
      Posted at 15:55h, 18 July Reply

      Thank you Nancy! We had a great night out with Italian tapas! Yes, I often have to do this with belts and I am not a fan of them just hanging there, so I learned this trick!

    Posted at 16:01h, 14 July Reply

    Happy belated birthday Jess!
    I love your tailored shorts on your long legs!
    I still wear Bermuda-style shorts because I have very veiny legs that bother me.
    Even when I golf I wear long skorts.
    Anyway, it sounds like you had a wonderful dinner! Nothing like Italian food to celebrate birthdays!

    • Jess Jannenga
      Posted at 15:40h, 18 July Reply

      Thank you Robin. I have been loving some tailored looks and look forward to styling them in the Fall. I like Bermuda shorts too!

  • Marie
    Posted at 14:03h, 14 July Reply

    Classy look, indeed. I love the statement belt you used.
    Enjoy you Summer!

    • Jess Jannenga
      Posted at 15:41h, 18 July Reply

      Thank you Marie! I have several belts from Mango that are my favorite as they add that “extra” !

  • Heike Yates
    Posted at 15:24h, 13 July Reply

    Jess, I love that combo with reptile patterns. Is that this summer’s trend?

    • Jess Jannenga
      Posted at 10:39h, 14 July Reply

      No, but it is one of my favorite clutches. JJ Winters makes great leather bags.

    • Jess Jannenga
      Posted at 15:41h, 18 July Reply

      Hi Heike, no, the croc bag or print is not a summer trend, I just love to add texture to looks. Thanks for stopping by!

  • Michelle
    Posted at 10:05h, 13 July Reply

    Belated Happy Birthday, Jess! Sounds like you had a lovely celebration. Very attractive outfit. Love the belt. I’m with you about wearing less jewelry in the summer. It can just be too clingy.


    • Jess Jannenga
      Posted at 11:00h, 13 July Reply

      Thank you Michelle! Yes, this and my dark brown belt from Mango are my favorites and I have alot to wear them with.

    • Jess Jannenga
      Posted at 15:42h, 18 July Reply

      Thank you Michelle! We did. Yes, I will wear a simple chain or scarf if it isnt too hot!

  • Michele
    Posted at 18:42h, 12 July Reply

    Hi Jess, Wishing you the happiest of birthdays and a fantastic trip to Italy! Can’t wait to see what you bring home!! Looking fabulous as always. xo, Michele

    • Jess Jannenga
      Posted at 11:01h, 13 July Reply

      Hi Michele, thank you so much! We are going in Oct and I am looking forward to it!

    • Jess Jannenga
      Posted at 15:43h, 18 July Reply

      Thank you Michele! I can not wait! This trip has been a long time coming! ( Covid!) It will be a tough decision! LOL.

  • Neti
    Posted at 00:20h, 12 July Reply

    Happy Blessed Birthday my Lovely Friend! Hope you get something nice in Italy, Shoes and Handbag.
    Enjoy July. . .

    • Jess Jannenga
      Posted at 11:02h, 13 July Reply

      Thank you Neti! I look forward to looking 🙂 Enjoy this month too my friend!

    • Jess Jannenga
      Posted at 15:43h, 18 July Reply

      Thanks so much Neti! It will be fun and I cant wait to explore! Oh yes, perhaps both? LOL

  • Carrie @ Curly Crafty Mom
    Posted at 20:43h, 11 July Reply

    Happy birthday! Ohh, spending money for a special gift in Italy sounds perfect! That belt alone is so cute, but I love it paired with those shorts and the white top!


    • Jess Jannenga
      Posted at 11:02h, 13 July Reply

      Thanks so much Carrie! It is one of my favoties to wear. It will be fun looking for sure!

    • Jess Jannenga
      Posted at 15:44h, 18 July Reply

      Thank you Carrie! I do love several of the belts I bought from Mango. I get alot of wear from them as I think they elevate the look.

  • Maureen
    Posted at 15:40h, 11 July Reply

    Happy birthday Jess! You look smashing in this summer outfit and kudos on such a classy styling. I am a handbag lover at heart so I vote for bags! So excited for you and your trip. I know you will have such a fabulous time!

    Maureen | http://www.littlemisscasual.com

    • Jess Jannenga
      Posted at 11:03h, 13 July Reply

      Thank you Maureen! I love both it will be a tough decision, but one that will remind me of the trip too!

    • Jess Jannenga
      Posted at 15:44h, 18 July Reply

      Thank you Maureen for the Bday wishes. I love handbags too, but I love shoes as well! haha. Cant wait!

  • Jodie Filogomo
    Posted at 09:39h, 11 July Reply

    Happiest of birthdays and I think you should bring back both shoes and a purse from Italy. Heck, you don’t go there every day!!!
    The belt is fabulous with this look!!

    • Jess Jannenga
      Posted at 11:04h, 13 July Reply

      Thank you Jodie! LOL. I like how you think!

    • Jess Jannenga
      Posted at 15:45h, 18 July Reply

      Thank you Jodie! And I love that you are enabler! I may do that !

  • Wendy
    Posted at 09:36h, 11 July Reply

    Happy Birthday Jess! You look awesome in this outfit. I never think to wear belts unless I’m holding up pants.

    Great post!


    • Jess Jannenga
      Posted at 11:04h, 13 July Reply

      Thank you Wendy! I used to not be a belt person, but I do love these styles of belt and find them very versatile.

    • Jess Jannenga
      Posted at 15:46h, 18 July Reply

      Thanks so much Wendy! I have a few thicker belts I have bought from Mango that I love to wear. They are not constricting and they give it that “extra” oomph!

  • Kellyann Rohr
    Posted at 04:47h, 11 July Reply

    Happy Birthday sweet friend! I am so sorry I missed it – I should have remembered you and my bother have the same birthday. I am excited about your trip to Italy and cannot wait to see what you bring back – I know it will be something fabulous!
    Speaking of fabulous, your outfit IS! I always love to see shorts classed up. Living in tourist heaven I have seen my fair share of shorts and tees. It’s not my style at all, I much prefer dressing them up just like this. Still cool and comfortable but looking so chic!

    • Jess Jannenga
      Posted at 11:06h, 13 July Reply

      Thank you Kellyann! I just prefer dressing up too! Since the shorts are tailored, it makes it easy to style in a elegant manner. Hope your brother had a great birthday!

    • Jess Jannenga
      Posted at 15:47h, 18 July Reply

      Thank you Kellyann! No problem! Happy Birthday to your brother! Yes, my mom never fails to remind me that I am almost “AARP age!” LOL. Hey, i’ll take it! Glad you like the look. I am not a tee shirt girl either, so for me, this is something I enjoy wearing

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