Bermuda shorts have a story as fascinating as the way we style them today. What started as a clever military solution in the sweltering Bermuda heat has become a fashion staple that refuses to leave the spotlight. These shorts keep reinventing themselves every season. At Dapper Diary, we are here to help you style them to perfection. It doesn’t matter if you’re a fan of Bermuda shorts, men’s styles, playful Bermuda short shorts, or lightweight Panama shorts; there’s a look here for everyone.
You’ll be surprised to know that your favorite pair of Bermuda shorts comes with quite a bit of history attached to it. We have to take a trip back in time. It’s 1916, World War I is raging, and soldiers stationed in Bermuda are melting under the hot island sun. Their wool uniforms don’t mix with tropical heat. Therefore, the troops all take a pair of scissors to their trousers and cut them down to knee length. That bold move gave birth to the first pair of Bermuda length shorts.
We did a little digging and found out some fun facts. Some credit Mason Berridge of the Bermuda Garrison for these stylish yet comfortable shorts. While others say Nathaniel Coxon, a tea room owner, was the original genius. The Bermuda shorts have made their way back, and we all see them as a cultural icon. They were once shaped by the island’s British style, but now you find them in every other shop. These shorts are now available in an explosion of color: pink sands, turquoise seas, pastel homes, and vibrant costumes.
Traditional Bermuda shorts followed strict rules. The hem of a good Bermuda short cuts right off above the knee. Therefore, it’s not too tight. You can pair it with dark socks, hard-sole shoes, a blazer, and a button-down shirt. Rebecca Singleton of TABS later broke barriers, creating Bermuda and shorts collections for both men and women, modernizing cuts and fabrics. These shorts have proven they’re more than just a summer fling. The best part is that these shorts are flattering for all shapes!
Anyone can style Bermuda shorts! The cat’s out of the bag. You might think we are pulling your leg, but these shorts are the easiest garment to accessorize. No matter what your style might be, these shorts will adapt. Now, if you’re wondering, “How do we make shorts and Bermudas work for different settings?” Here’s our personal styling guide from our stylists at Dapper Diary:
All fashionistas know that it’s not just what we wear, but when we wear it. Bermuda shorts aren’t just for summer. We are going to tell you that you have to layer your Bermuda shorts for all seasons.
We don’t have to look far to see how style icons influence us. Here are a few celebs showing us how it’s done:
✩ Rihanna: The billionaire pop icon likes to pair her Bermuda short shorts with oversized blazers and denim shirts.
✩ Pharrell Williams: He is known for pairing Bermuda shorts men’s styles with preppy sweaters and sneakers.
✩ Hailey Bieber: Always the flawless fashion icon, Hailey tends to style her casual Panama shorts with crop tops and chunky sneakers.
✩ David Beckham: If you want a more formal look, then David is your man. His formal look with crisp shirts and tailored Bermuda length shorts is definitely inspiring for men.
✩ Zendaya: She likes to play with textures, mixing leather Bermuda shorts with structured coats.
If they can make it work on the red carpet or in street-style snaps, so can we!
Accessories can take your outfit from basic to breathtaking. Here’s how to style it right:
At the end of the day, Bermuda shorts are a comfortable and stylish addition to your wardrobe. They’ve gone from a wartime necessity to a fashion staple spotted everywhere. You can find them everywhere, from boardrooms to beaches, from Bermuda to Paris runways. Bermuda shorts adapt to us, not the other way around. At Dapper Diary, we love looks that are easy to pull off and are easy to achieve. Therefore, the next time you’re wondering what to wear, remember: Bermuda shorts are never out of season. These shorts are just waiting for your unique twist!
➥ Why are they called Bermuda shorts?
They got their name because the style was created and popularized in Bermuda as a cooler alternative to trousers. We see them as a blend of island practicality and timeless fashion that spread worldwide.
➥ What is the difference between shorts and Bermuda shorts?
Regular shorts usually end mid-thigh, while Bermuda shorts reach the knee or just above. You’ll notice Bermudas are more tailored and versatile, perfect for casual and semi-formal looks.
➥ What body type looks good in Bermuda shorts?
The beauty of Bermuda shorts is that they flatter every shape when styled right. You can balance the proportions with fitted tops or flowy blouses, making them work for all of us.
➥ Are Bermuda shorts still in style?
Yes, they’re a major trend in 2025, seen on runways and styled by top celebrities. We love them for their mix of comfort, sophistication, and endless styling options.
➥ Are Bermuda shorts frumpy?
Not if you style them correctly. Balance is the key, and you have to understand that fit and proportion matter most. When you pair them with chic tops, sleek shoes, or blazers, Bermuda shorts look anything but frumpy.
Lena lives for bold fits, viral looks, and saying what everyone’s thinking in a way that resonates. A style-savvy Gen Z queen with a soft spot for streetwear and red carpet drama, Lena only has one rule: “Serve every day like it’s Fashion Week.” Catch her dropping truth bombs, style inspo, and outfit slays at Culture Club and Slay Report!
