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!

More Bermuda Shorts Options

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