How to Wear Bermuda Shorts Without Looking Frumpy! - Elegantly Dressed and Stylish
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How to Wear Bermuda Shorts Without Looking Frumpy!

How do you wear Bermuda shorts and not look frumpy? I have a few tips to ensure you’ll look stylish!

Plaid tank with denim bermuda shorts and white sandals

Plaid tank in red and pink

Paige Bermuda Shorts

What makes them Bermuda Shorts?

“The invention of Bermuda shorts is attributed to native Bermudian and tea shop owner Nathaniel Coxon, who in 1914 hemmed the uniform pants of his employees allowing for more comfort in the heat. The British Army, stationed in Bermuda during World War I, adopted the shorts for wear in tropical and desert climates. “

Bermuda shorts are considered an ageless style and can be styled a bit more formally if desired. They certainly don’t have to be dowdy or frumpy! Showing on various retail sites, I thought I would discuss how to dress or style the pair.

I received these Paige denim shorts as a part of a gifted thrifting experience in Charlotte. I have worn Paige denim before and was excited to find these as I wanted a pair to dress up. I prefer wearing these shorts with espadrilles, wedges or sandals as to keep the leg line long.  I will style these shorts with blazers and wear them as a dressier style, whereas my shorter denim shorts ( 4″) are worn in a more casual style.

I’ve styled shorter denim shorts IN THIS POSTTHIS POST shows the shorter denim length ( 4″) in a more casual style. It really is about your comfort level. I wear both lengths depending on my mood and how I want to style them.

What shoes to wear with Bermuda shorts?

You want to keep the leg line long, so here are a few suggestions, since they are about 1″ above the knee:

  • Wear a neutral or nude shoe so that the leg line does not get cut off and shorten the look of your leg. I am wearing a white strappy sandal from Zara. The strappy sandals shows more of the foot, and continues the leg line.
  • Wedges
  • Pointed flats, as they continue the leg line as well.

When styling Bermuda shorts, there are several types. One, is the Bermuda short with a looser fit in the thigh, the other more of a skinny jean counterpart, so fitted more through the legs. Proportion and fit is key here, so if the shorts are a bit more relaxed, style a fitted top with them. Conversely, if they are more fitted in the thigh, a blousy tank, such as the one I am wearing makes a nice balance

I have styled these denim shorts with a halter from J Crew ( thrifted $5 find!) and the proportions balance out. The sleeveless blouse adds a feminine touch by the colors here as well as the halter style. The large pink flowered earrings also add to the feminine touch.

White eyelet blouses and other detailed white blouses would be lovely to wear with denim Bermuda shorts. A crisp white top with denim is always a good look.

There are also Bermuda shorts that are more tailored. If you aren’t a fan of denim, but prefer a linen or lighter fabric for the Summer, have a look at this gingham pair and these, in a cotton and lyocell, Tencel and spandex blend . ( which would make them breathable and soft)

These paperbag waist Bermuda’s from Mango, are a fun style and come in blue denim and ecru.


I am 5 foot 9, so you will want to take into consideration your height with Bermuda shorts. Remember the 2/3  -1/3 rule, and decide whether you want to try them.  There certainly are other options if you find these are too long for you, but the shoe trick is most helpful!

If you like or love your legs, but still want coverage, these shorts are a great way to show the lower legs as well as staying cool in the heat!

Plaid tank with denim bermuda shorts and white sandals

Pink large flower earrings

Do you or have you tried Bermuda shorts, or do you prefer a shorter length? Maybe you don’t wear shorts at all. Let me know in the comments, I love to hear from you!


Paige denim Bermuda shorts c/o Green Consignment ( similar)

J Crew halter c/o Green Consignment

Zara white strappy sandals  ( love these!)

Zara white bag  ( similar)


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  • Leslie Susan Clingan
    Posted at 21:36h, 16 May Reply

    Always perfection. I dislike my legs more this year than ever before. But I am not ready to give up shorts yet!! And I am working to get them back in better shape. In the meantime, these shorts might be just what I need. You look smashing in them. Not the least bit frumpy. I appreciate your tips for continuing the elongated leg and ways to balance the fit of the shorts with the best fit in the top. Great find in your top from J Crew. I like the way it shows off your shoulders. Fun summery print.

    • Jess Jannenga
      Posted at 09:58h, 18 May Reply

      Thanks so much Leslie! You might like this style of short. I like Paige denim, so I knew these would be quality. Glad you liked my tips! I loved the J Crew print and couldnt beleive it was $5!

  • Emma Peach
    Posted at 18:48h, 11 May Reply

    Fab summer outfit! I love the halter top, it looks great with the denim shorts. I prefer longer shorts, they’re more versatile than short shorts. I’ve seen some really nice longer shorts and skorts with matching tops in Zara recently – I’m very tempted but might hang on for the summer sale!

    Emma xxx

  • Lee
    Posted at 11:10h, 10 May Reply

    You look so pretty! Love this top!
    Lee | LegalLee Blonde

  • mireille
    Posted at 10:43h, 10 May Reply

    I love this top. I enjoy wearing my bermudas with tanks and fun shoes and also with a kimono.

    • Jess Jannenga
      Posted at 11:42h, 11 May Reply

      Thank you! It is amazing I even saw it, as I was looking at racks and racks of tops at a Thrifting event. They are a fun style to try out!

  • Shelbee on the Edge
    Posted at 09:18h, 10 May Reply

    This is such a cute outfit, Jess! I have to style my Bermuda shorts more often. I love yours. The length is really great and they look fabulous on you!


    • Jess Jannenga
      Posted at 11:43h, 11 May Reply

      Thank you Shelbee! I do wear shorter shorts usually, but wanted to try them. I think they allow for more dressy looks. 🙂

  • Cheryl Tucker
    Posted at 09:17h, 10 May Reply

    This is a fabulous and on trend look! Longer shorts are everywhere now and I am loving it! It is a whole new silhouette to play with! Love your beautiful top too!

    • Jess Jannenga
      Posted at 11:43h, 11 May Reply

      It is! I thought the denim ones were neat and adds variety to my summer wardrobe. Thanks! I loved te top too 🙂

  • Claire Justine
    Posted at 03:18h, 10 May Reply

    Great look, Jess. Love your top, it’s beautiful 🙂

    • Jess Jannenga
      Posted at 11:44h, 11 May Reply

      Thank you Claire! I am a fan of this type of halter

  • Suzy
    Posted at 02:25h, 10 May Reply

    I have a sexy look I’m posting on Friday with Bermuda shorts! This is great advice, Jess.
    Suzy xx

  • Jodie Filogomo
    Posted at 17:17h, 09 May Reply

    This is gorgeous Jess. I have one pair and they are easier to sit in since they are longer.

  • Maureen
    Posted at 15:39h, 09 May Reply

    You styled it beautifully Jess! I am not a huge fan of shorts in general but I like Bermuda shorts. I find the length to be appealing and perfect for the dog days of summer!

    Maureen |

    • Jess Jannenga
      Posted at 11:53h, 11 May Reply

      Thank you Maureen! I do prefer dresses, but have some 4 inch denim shorts. I thought these would be fun to dress up a bit. I appreciate your comment! Enjoy your week!

  • Olivia
    Posted at 13:33h, 09 May Reply

    Great article as always, thank you for sharing!!!

    Love and Wellness

  • Kellyann Rohr
    Posted at 05:04h, 09 May Reply

    I love that top Jess! The colors and the halter style are so flattering. I am all about the bermudas lately. IN fact I’m doing a post on Thursday all about them, I just can’t get enough!

    • Jess Jannenga
      Posted at 11:51h, 11 May Reply

      Thank you! I love it too, it was a thrift store find! I look forward to your bermuda post!

  • Lovely
    Posted at 02:47h, 09 May Reply

    This is a beautiful look for summer. The top is lovely, and your earrings are cute!

    • Jess Jannenga
      Posted at 11:46h, 11 May Reply

      Thank you Lovely! I wanted to give the bermudas a go again, just trying something different. I appreciate your comment!

    • Jess Jannenga
      Posted at 11:52h, 11 May Reply

      Thank you! Yes, this time of year I take out my big floral earrings!

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