How to Wear Bermuda Shorts Without Looking Frumpy

Greetings, friends! Happy Friday and cheers to the weekend! Today we’re wrapping up 21 Days of Summer Fashion, and I’m talking about how to wear Bermuda shorts without looking frumpy.

I’m actually going to have a bonus summer outfit tomorrow because I have the pictures, and what I’m featuring is on sale this weekend, but today I want to share an outfit with Bermuda shorts.

How to Wear Bermuda Shorts Without Looking Frumpy: Many women over a certain age don’t want to wear short shorts, but Bermuda shorts can skew frumpy, so I have some tips to help you choose and style these longer shorts to create a look that is stylish and flattering.

Many women over a certain age don’t want to wear short shorts, but cropped pants can be hot, and let’s face it, we don’t always want to wear dresses, so they often opt for Bermuda shorts. But Bermuda shorts can skew frumpy, so I have some tips to help you choose and style these longer shorts to create a look that is stylish and flattering.

My first tip is to compare inseams. A lot of Bermuda shorts are 10 or 11 inches long. That is reeeeally long on some of us. Of course, it depends on your height, but at 5’5″, shorts with an 11″ inseam come all the way to the tops of my knees.

These denim Bermuda shorts have a 9″ inseam, so they’re still long enough to cover most of my thighs, but they end an inch or two above the knee, which I feel is a little more flattering. It makes the leg line look a little longer, just enough to keep me out of the frump-zone.

The other thing to note is that these shorts fit my thighs really well. You want your shorts (this goes for any length) to follow the line of the leg and keep a slender silhouette. You don’t want them to be tight enough to pull across your thighs, but you also don’t want them to stick out from your leg, especially at the leg opening — that creates visual weight and a boxy silhouette.

See how when you look at this outfit straight-on, I look balanced, and you can see an hourglass shape. The shorts taper just enough to follow the line of the leg, and the shirt fits well too — we’ll talk more about that below.

How to Wear Bermuda Shorts Without Looking Frumpy: Many women over a certain age don’t want to wear short shorts, but Bermuda shorts can skew frumpy, so I have some tips to help you choose and style these longer shorts to create a look that is stylish and flattering.

These are obviously denim shorts, and you can see they have a cuff. This doesn’t bother me personally, but it does draw attention to that area of the leg. You want to make sure you’re okay with that.

So next, let’s talk about shoes. Your shoe choice is key when styling Bermuda shorts.

I chose gold flat sandals that are strappy and delicate. These disappear for all intents and purposes when you look at my overall outfit. Because of that, they make my legs look longer, which is really important when wearing longer shorts. If I wore shoes with a higher shaft (meaning the front part of the shoe comes up higher on the foot, it shortens the line of the leg and can make your legs looks stumpy.

If I wanted to wear a sneaker with these, I’d stick with the Converse Shoreline in a light color. The Shoreline has a slighter shorter shaft than the regular Converse that come up right to the ankle, and help elongate the leg a bit more. Even an inch helps.

A heel would also help this look — a wedge sandal in a light neutral is always a good choice with Bermuda shorts, but I wanted to keep this look casual and practical — something you may wear to run errands or watch the grandkids.

How to Wear Bermuda Shorts Without Looking Frumpy: Many women over a certain age don’t want to wear short shorts, but Bermuda shorts can skew frumpy, so I have some tips to help you choose and style these longer shorts to create a look that is stylish and flattering.

On top, I wore a simple white v-neck tee. There are a lot of reasons why this top looks good with these shorts — and why it looks good on me in general.

First, the neckline. Knowing your body type is really important when choosing basic wardrobe pieces like t-shirts. A v-neckline is far more flattering than a crewneck on women with a short neck, wide shoulders, and/or a large bust. I have all three, which is why I’m so fond of V-neck tops! I also like how a V-neck or scoop neck features the thinnest part of a woman’s body — her collarbones.

If you have a smaller bust, long neck, narrow shoulders, and/or short hair, a crewneck will visually shorten the length of the neck and widen the shoulders, so that’s a good choice for you. That doesn’t mean you can never wear a v-neck, but it’s something to keep in mind when choosing tops and putting outfits together.

This tee in particular is one of my favorites, and I think the shape of the V is perfect — not low enough to be immodest, but it elongates the neck and draws the eye in and down towards my waist.

I also like the slub cotton material — it’s more modern looking than pima cotton tees — and the length of the sleeves is nice too. It is a little boxy, but the material has a nice drape so it lays against the body (as opposed to billowing out and creating visual weight.) Then a little front-tuck action gives it some shape though the waist, and that also shortens it enough to give the overall look balance.

How to Wear Bermuda Shorts Without Looking Frumpy: Many women over a certain age don’t want to wear short shorts, but Bermuda shorts can skew frumpy, so I have some tips to help you choose and style these longer shorts to create a look that is stylish and flattering.

A white tee and jean shorts is as basic as it gets, but my jewelry levels up this casual look and keeps it looking fresh. I love this 3-disc necklace for filling a v-neckline. As you know, I wear it a lot.

Since I’m bigger busted and have a short neck, I’ve never been a fan of statement necklaces. They add bulk in an area I’m trying to open up, plus they’re just heavy and uncomfortable in my opinion!

The delicate, layered look of this necklace is flattering (plus it’s a hot trend at the moment!) and it adds interest without overwhelming the simple outfit.

I also added these fun white hoop earrings. White earrings draw attention to your face, and in this case, they repeat the white from the t-shirt too. Unfortunately they were discontinued, but there are lots of great options available that will achieve the same effect.

How to Wear Bermuda Shorts Without Looking Frumpy: Many women over a certain age don’t want to wear short shorts, but Bermuda shorts can skew frumpy, so I have some tips to help you choose and style these longer shorts to create a look that is stylish and flattering.

I also wore my Alex and Ani charm bracelets. They’re my go-to for casual outfits when I’m wearing gold. I like the casual vibe, and again, they have that delicate layered look that I find appealing.

The handbag options for this look are virtually endless, but you can’t go wrong with a cognac bag when you’re wearing white and denim with gold accessories. I love the warm neutral against the cool color palette of the white and blue. Of course, a pop of color or print would totally work as well and be fun with this outfit. If I’d had my red tote at the time, I probably would have carried that instead.

I can also see wearing wedge sandals with this outfit and carrying a fun clutch to go out to eat with friends in the summertime.

Anyway! I hope it was helpful to dissect why this outfit works and how to wear Bermuda shorts without looking frumpy. At the end of the day, we all have to dress for our unique bodies — no one outfit formula will work for everyone, but with these tips, hopefully you will feel more confident as you put your summer shorts outfits together and determine what works best for you.

How to Wear Bermuda Shorts Without Looking Frumpy: Many women over a certain age don’t want to wear short shorts, but Bermuda shorts can skew frumpy, so I have some tips to help you choose and style these longer shorts to create a look that is stylish and flattering.

white tee // 9″ denim Bermuda shorts // gold sandals (option) // 3-disc necklace // bracelets // similar hobo

photo credit: Alison Cornell

Be sure to visit Cyndi and see the summer outfit she’s styling today!

In life events, we settled on our new house yesterday, and I’m super excited about that! We’ll be over there today, cleaning and getting the backyard space set up. I’ve been sharing a little bit every day in my daily emails, so if that’s of interest to you, make sure you’re signed up!

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60 Responses

  1. I have never once thought of Bermuda shorts as frumpy, but the total opposite;  especially if they are in a fabric other than denim.  They look so much more dressed up than regular short shorts.  I wear all lengths of shorts, but lately I have been drawn to Bermuda’s more and more because I think they are more dressy.  Your tips are fabulous though.  Maybe it is all about the inseam and the cuff.  

  2. Thank you for this post it is so useful – it is amazing what a difference footwear and accessories make! Good luck with your move!

  3. So excited for you ….I close
    Monday morning and look forward to
    seeing your new home!
    Great info on how to choose shorts…
    I will be getting rid of a few of mine
    didnt realize how they really fitted.

      1. Movers coming Monday afternoon….weird time to move.
        Closing in the morning …moving to my new retirement
        Condo.  Praying for God to lead me in this new
        Stage of my life.
        Saw your new house beautiful!,,,Can’t wait to see
        how you decorate! I love the open floor plan and of 
        Course the deck and 🏊‍♀️ pool!

  4. Thanks so much for sharing your knowledge on the do’s and dont’s of wearing Bermuda’s. It was really helpful with great tips! I’m excited for you as you decorate your new home and loved your instsagram story. 

  5. So excited for you and your new house!  We just got moved into our beautiful new house this week and it’s wonderful to only have one house to worry about 😍.  
    Please send some of your rain down here to  Arkansas!  We are dry and burning up down here with temps in the high 90’s.  
    Thank you for your posts!  I feel like you are a good friend 💗. Have a great weekend!

    1. Congrats on YOUR new house!!! No rain here, and it’s hot at hades, but the kids have been having a blast swimming in our pool, and our best friends came over last night and all the kids were in there swimming. It was awesome. 🙂

  6. Okay…outfit is great, as usz.

    But SO excited for you on your house!!!  Busybody me loved your IG tour.  The yard IS beautiful and super private…you will LOVE that!!!  We were working on that from day one so how great not to have to worry about that!   
    Love your house layout.  Although ours is somewhat  different, we have similar features, so I am looking forward to seeing what you and your designer decide.  We are always in progress here…  

      1. You’re so nice!

        I Home Dec like the blind squirrel who occasionally finds a nut.   But I do blog about my adventures figuring it out.

        We’re outside now, ripping apart  our back yard again.   

        “Real” bloggers for inspo:  if you’re into Uber traditional, check out Laurel Bern.   Colorful and creative, Kristi at Addicted2Decorating.  I tend to like to borrow from each.  

        All the best to your fam!

  7. Thanks for posting about this. I am not a short shorts person. All of mine are Bermuda shorts, and I do worry about looking frumpy or aged in them, so this was very helpful
    for me. Enjoy your new bome!

  8. I bought a pair of the WHBM denim shorts when you featured them earlier. So cute and comfy! Thanks!!! One of my girlfriends liked them so much she bought a pair too. Oh, and your sizing info was very helpful, since I was shopping online. Thanks again. I doubt I would have tried these shorts if I hadn’t seen how nice they look on you!

  9. THANK YOU, THANK YOU, THANK YOU!  This is a very helpful post for this almost 62 year old.  I will explain.  I really like the Kim Rogers Bermuda shorts I have, but I don’t love them, and now I know why.  The legs are too full!  Until I can find a white and tan pair to replace them, I will have to wear them.  I do struggle selecting a top from my closet that looks good with them.  The W&W bermuda cuffed jean shorts have the right fit on my legs, but they are a smidgen too long because they come to the top of my knees.  You would know that I placed an order with Target last night, spending enough for free shipping.  I am going to order the Universal Thread bermuda jean shorts today, since I love the other Universal Threads items I’ve purchased.  Question:  Do you have to wear a tank under the white tee you have on in this post?  I have it ready to wear now, but it looks see thru to me.  Thanks!

    1. Yes, especially if you have thinner legs (which I think you have said you do) finding shorts that fit close to the thighs is key to a streamlined, slender look. 🙂 Let me know how you like the Universal Thread bermuda jean shorts. And I do not wear a tank under this tee. I just wear a nude bra, and I don’t feel it’s too see-thru.

  10. I learn so much when you discuss the why’s and why not’s of an outfit! Please do more of these educational posts in the future. While Bermuda shorts have never been my favorite, I now feel equipped to possibly give them a try. So happy for you all and your new house! Have fun!

  11. Jo-Lynne, thank you so much for these valuable tips!  I have been struggling for years to style Bermuda shorts in a flattering way.  I have since given up and accepted that shorter shorts look better on me and flatter my legs best…even though I am over 40, I stopped caring about my shorts being too short and have embraced that my legs are my best asset and I will show them off if I like!  However, that being said, sometimes longer shorts are more practical and I keep one pair of Bermuda denim shorts for when I need them…I think I will pull them out again and see if I can’t follow your tips and create a flattering outfit for myself.  Thanks for the inspiration!


    1. I’m with ya, Shelbee, most of us do look best in shorter shorts. Not necessarily “short shorts” but a nice mid-length. But yeah, sometimes it’s nice to have a longer pair.

  12. You have encouraged me greatly to get back into my shorts… I’ve picked up three new pair so far. I’m still on the hunt for a denim pair which I have never owned at any age… strange right? But I always felt for me the denim too hot and uncomfortable but I’d like to find a lighter weight denim pair if I can( you and Cyndi make them look so good).. Maybe for the cooler days:). I’ve tried Bermuda shorts and at 5’3 it’s not been pretty lol 😂 my leg disappears and my knees get bigger uggh no way!!… definitely the inseam should be my focus. Thanks again and enjoy your new house this weekend can’t wait for the pics😀 you look nice in the Bermuda shorts but with your legs you can definitely rock the shorter ones:)

    1. Yeah, at 5’3″ this is probably not a great length of short for you. If you found a 7″ inseam, it might look similar to how these look on me. But I still maintain that a 4″ or 5″ is the most flattering length on *almost* any woman. At least those of us who are average height or shorter.

  13. Great tips as usual! I love bermuda shorts…. Thanks for including them. Good luck with the home decorating. I’m not on Instagram so please do include pics on your blog if you can for those of us who are social media – filled up!😂

  14. OH.MY.GOSH!!!!! I just watched your Insta Story about your new house and I totally LOVE every single thing about it!! You scored!!!!! I can’t wait to see how you decorate it! I am so excited for you and your family! (Makes me want to buy a new house :)))

  15. I love the denim Bermuda shorts and t-shirt look. I am 5’3″ so I wear wedge sandals and just bought a pair of leopard print wedges. You look amazing in the Insta Story of your new house. The house is a dream for sure and your pool and back yard are heavenly. I could hear the birds. congratulations you deserve it all!

  16. Hi — just wanted to share an idea for denim Bermuda shorts. I took an old pair I just don’t wear very often and cut the legs to a 9″ inseam (when cuffed). I use that handy (no-sew) ironing tape to hold my cuffs in place and I still have that cute frayed edge on the top of the cuff. Free shorts!

  17. Love that look 🙂 I’m wearing longer shorts as I get a little older so it helps to see them on your blog and the way you style them. Have a good weekend everyone.

  18. So happy for you about the house! Exciting!! I am sorry but I still think Bermuda shorts look frumpy. The exception for me is if they are a dressier short. Then I can sometimes do it. I think it is because I am so short. They cut my legs right off.

    1. They’re definitely not the most flattering style on many, but I see why some women like them. The important thing is knowing what works for you so you can syphon thru all the info that’s out thtere – including mine. Ha! 🙂

  19. These are great tips Jo-Lynne! I’ve stayed away from Bermuda shorts in the past few years because I’m a lot shorter than you! Maybe, I need to rethink whether I can wear these shorts and do a little investigative shopping. It is amazing how the way a piece of clothing is made or the lines of it in any style can change the way it looks on each of us!


  20. J Crew Factory’s Frankie shorts have worked really well for me – a 9-inch inseam and very tailored look.

  21. That was interesting – thank you!  Those shorts look great on you, but I understand why you prefer yourself in shorter shorts, and you certainly have the legs to carry off whatever length you like.  I struggle with shorts.  I like the idea of longer shorts, but I agree that they can be frumpy.  After reading your post, I wonder if the problem for me is my short legs.  Even though I’m taller, my legs are relatively short, and the long shorts make them look shorter.  Lately, I’ve been trying to find a 6 or 7 inch inseam, which feels like a good compromise (I don’t like myself in short shorts just cuz).  They’re hard to find though – do you think that suggests that they don’t actually look good on anyone…?  Anyway, I also appreciated your insight on tops (with a longer body and neck, and a small bust line, I now get why a round neck is not the worst thing for me (or why the v-necks that look amazing on you sometimes look like they hang on me).  So yeah, really helpful!  And congrats on the house stuff!!

    1. Different lengths flatter different body types so I’m not sure why 6 or 7 is so unusual to find. I feel like I’ve seen a 7″ inseam somewhere but I can’t remember where.

      1. Thanks for the suggestion!  I realized after I sent my comment that what I’ve been having trouble finding is jean shorts without a cuff (with a rough edge) in that length.  Not sure why, but I’ve never loved cuffed shorts on me….I’m probably just being picky.  I love those Old Navy shorts though – I should get over there and try those on.

        1. I don’t think that’s being picky. The cuff cuts off the leg, so if you have shorter legs, it’s probably not the best choice. And yeah, longer shorts with the raw edge are hard to find — but maybe cutting off some jeans or Bermuda shorts would work.

        2. Talbots also carries a 7” short in a bevy of pretty colors with a cute button detail on the leg and they also come in Petite! 

  22. Congrats on your new house! I’m not on instragram so looking forward to seeing your posts and pictures  about your house! I think I have that same rug or something very similar and we have it in our dining room. We recently renovated our kitchen, redid all our hardwoods and repainted the main level and upstairs hallway ( it’s all open concept so had to continue it up the stairs) and got new furniture too so it’s exciting to hear about your decorating! Best wishes! 

  23. Another exceptional post that resonates with many of your readers and it is chock full of information. Thank you, Jo-Lynne! Have a great weekend!

  24. Lots of great tips here! Love this outfit with the pop of gold from your sandals.

    I enjoyed the summer series! Thank you for all of your hard work, especially during such a busy season in your life. 

  25. Hi, I really enjoy your blog. I’m down here in the South and like to read about your hot weather outfits. This has been an interesting summer, too, because my daughter graduated from college and is now on the visual merchandising team at a large Nordstroms. They really put in the hours, even though it sounds like a fun and creative job. I remember that you said Nordstrom is one of your favorites and it is one of mine, too.

  26. Great tips on wearing Bermuda shorts! Do you find the Gorjana necklace tangles a lot? Was interested in purchasing but several reviews said it tangles constantly while wearing.

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