5 Fabulous Ways to Style Denim Bermuda Shorts

I have always liked long denim shorts but I am especially excited about the ways I am seeing them styled this season. The denim Bermuda shorts trend is ideal for women over 40 and here’s why. First, the longer length shorts can hide any issues you may have with your upper legs (including a few extra bumps and bulges, crepey skin and veins). Second, they are casual and chic and come in a variety of styles from oversized and distressed, to sleek and fitted. So you are bound to find a pair that will work for you. And last but not least, you can style them a lot of cool ways, just like your favorite jeans.

How To Style Denim Bermuda Shorts

I am thrilled Net-a-Porter is back up and running again, because it is my go-to site for sophisticated styling. I am also impressed with H&M for how they put together their looks. So between the two, I found 5 fabulous ways to style denim Bermuda shorts for women over 40. And I’ll show you how you can style the looks substituting some of the pieces with looks for less.

white denim bermuda shorts with jacket
FRAME Le Vintage Bermuda frayed denim shorts, $200

1. Long Jacket + Bermuda Shorts

My absolute favorite way to wear denim Bermuda shorts this season is with an oversized jacket. We saw bike shorts with menswear jackets in 2019, but only fashion models or 20 year-olds could pull off that look. This is where slim-cut Bermudas can come in and take the place of bike shorts for a similar look. Note how Net-a-Porter kept the base of this white FRAME denim shorts outfit look clean with a white tank top. Slip on some slides and grab a white bag and you are good to go! Shop my looks for less below.


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white t-shirt dsitressed bermuda shorts fountainof30
GRLFRND Beverly distressed denim shorts, now $126

2. Basic Tee + Distressed Shorts

You love the look of a white t-shirt with your jeans, so top off a pair of distressed denim Bermudas like these from GRLFRND (now on sale) with one of your (unstained) favorites. Try a basic oversize tee or one with cap sleeves or strong shoulder as shown above. Keep the accessories neutral and wear this basic hue with gold jewelry for a fresh summery look. See more shopping options for less below.


all black bermuda shorts and silk blouse
FRAME Le Vintage Bermuda frayed denim shorts, $200

3. Monochrome Blouse + Bermuda Shorts

An all-black ensemble of an oversized blouse with slim black Bermudas shorts is so simple and elegant! You can do this with any other solid color as well. However this all black look is perfect for casual cocktail attire. French tuck (tucked in only at the front) the silky blouse (no belt needed) and slip a shiny crocodile embossed handbag under your arm. High heel t-strap sandals will elongate your legs too. Shop the look for less below.


rolled denim bermuda shorts white shirt fountainof30
H&M Embrace High Bermuda Shorts, $29.99

4. Oversized White Shirt + Denim Bermuda Shorts

This pair of cuff hem Bermuda shorts from H&M are only $29.  I adore the easy-going styling with an oversized menswear shirt and black strappy mid-heel sandals. Wear the shirt out or with a French tuck. Shop the look below.


denim bermuda shorts with Balenciaga flat shoes fountainof30
Citizens of Humanity Claudette frayed organic denim shorts, $200

5. Bermuda Shorts + Ladylike Flats

You can wear just about any shoes with long denim shorts (including slides, flat sandals and sneakers). I like the surprise element of a pair of point toe slingbacks with these Citizens of Humanity frayed charcoal grey shorts. You don’t have to get Balenciaga logo-embellished flats (of course unless you want to) because you can find similar shoes for less. See my selections below.

How To Get the Best Fit

Denim Bermuda shorts are similar to a pencil skirt in that they flatter many women. Find a length that looks best on you, usually just above the knee or allow them to hit the middle of the knee. The looser styles are great for hiding imperfections, much like pair of boyfriend jeans. If you wear one of the loser distressed styles, just be sure that they are not too baggy or sloppy and keep holes to a minimum.

Can you cut a pair of jeans you own to get the look?  Yes, but be sure to start with a pair of high-waist jeans to get the look, and always measure before you cut! Cut them an inch or two longer just in case! You can always cut them shorter but you can’t grow them back!  See more Bermuda shorts styling tips here.

Are you going to try the Bermuda denim shorts trend this season?

Carol Calacci

You may also like to read more of Carol’s style posts for women over 40 like How To Shop Walmart Designer Fashion and Save Money and How To Style A Patio Party Maxi Dress High Or Low.

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