From Street Style To Staycations: How To Wear Bermuda Shorts Without Looking Frumpy

Bermuda shorts are having a serious moment, and not just on resort runways or throwback Pinterest boards. Once dismissed as dowdy or too practical to be cool, they've made a roaring return to the fashion circuit, this time with edge, attitude, and a refreshing versatility that suits every lifestyle.

These knee-length staples may conjure up school uniforms or tourist clichés, but with a few clever styling tricks, Bermuda shorts can transform into the ultimate wardrobe chameleon. Whether paired with polished tailoring or dressed down for laidback lounging, they strike that elusive balance between comfort and confidence. And yes, they're the ideal piece for everything from high-street adventures to seaside staycations.

So, what's the secret to pulling them off without looking frumpy? Let's unpack the style strategies that'll have Bermuda shorts working overtime in your wardrobe.

From Street Style To Staycations: How To Wear Bermuda Shorts Without Looking Frumpy
Photo Credit: Pexels

1. Find The Perfect Fit, Say Goodbye To Saggy Silhouettes

The cut makes all the difference when it comes to Bermuda shorts. Ill-fitting pairs can overwhelm your shape, making the whole look feel a bit… meh. Instead of grabbing the first baggy pair off the sale rack, take time to find a cut that flatters your figure.

Opt for a mid-to-high rise to define your waist and elongate your legs. Tailored Bermudas with a slight taper or a structured finish offer a cleaner silhouette, think more ‘smart-casual' than ‘lazy Sunday'. Avoid overly stiff fabrics or excess pleating, which can add bulk in all the wrong places. A crisp cotton blend or soft linen with a hint of stretch keeps the look sleek without compromising comfort.

When trying them on, check that the hem hits just above the knee or slightly below; this subtle tweak can instantly sharpen the look. Think of them as trousers that decided to have a bit of fun.

2. Balance Is Key, Pair With Slim Or Cropped Tops

Styling Bermuda shorts is all about proportions. Since they offer more coverage on the bottom, the trick lies in creating contrast up top. A billowy blouse or oversized jumper may sound cosy, but when paired with longer shorts, the effect can veer into sack-of-potatoes territory.

Try fitted tank tops, tucked-in tees, or cropped shirts to show off your waist and add some structure. A sleek bodysuit is a game-changer, streamlined, supportive, and perfect for layering. If you're after a breezier feel, opt for a boxy crop or lightweight linen shirt with rolled-up sleeves and a half-tuck.

When done right, this balance creates a clean, contemporary silhouette that looks intentional rather than accidental. Think of it as fashion's version of harmony, loose meets fitted, long meets short, and frumpy gets the boot.

3. Dress Them Up With Blazers And Heels

Need to level up your Bermudas for brunch or a gallery date? Enter the power combo: Bermuda shorts, a tailored blazer, and a pair of block heels or strappy sandals. It's the kind of look that feels effortlessly put together but not overly done.

Go monochrome for a sleek finish, black on black, beige on beige, or even white with ivory for a touch of coastal chic. The blazer adds polish while the heels elongate your legs, balancing out the extra fabric of the shorts.

Feeling bold? Try a printed or pastel blazer for a pop of personality, paired with gold accessories and a woven bag. Whether you're heading to a rooftop bar or a smart-casual office, this pairing is your shortcut to sophistication, minus the stuffiness.

From Street Style To Staycations: How To Wear Bermuda Shorts Without Looking Frumpy
Photo Credit: Pexels

4. Keep It Casual With Trainers And Graphic Tees

Bermuda shorts can do cool-girl casual just as easily as they can do boardroom sharp. For those days when you want to keep it laid back but still look like you made an effort, reach for a pair of white trainers and your favourite graphic tee.

The key here is attitude; go for bold prints, quirky slogans, or vintage band tees to give the look an off-duty edge. Tuck in the tee or do a little front knot to avoid drowning your frame. Throw on a denim jacket or utility shacket for added layers and you're good to go.

This outfit is a weekend warrior's dream, perfect for markets, coffee runs, or just pretending you're in a coming-of-age film set in Hackney. Bonus points for topping it off with tinted sunglasses and a messy bun.

5. Go Monochrome For A Minimalist Vibe

Monochrome is the cheat code for making Bermuda shorts look effortlessly elevated. Dressing in a single colour, or tonal variations of it, adds cohesion and polish, even if you're just wearing a tee and shorts.

Think beige-on-beige, all-white, or charcoal greys for a timeless aesthetic. Playing with texture keeps it from feeling flat, try a ribbed knit top with linen shorts or a silk cami with cotton Bermudas.

The result? An understated, chic ensemble that feels fresh out of a lifestyle editorial. Add minimalist sandals, a sleek crossbody, and a clean low bun, and you've officially entered quiet luxury territory, without needing a stylist or a five-figure budget.

6. Lean Into Holiday Mode With Breezy Fabrics

Planning a staycation or beachside getaway? Bermuda shorts are made for warm days and casual strolls, especially when they come in airy fabrics. Think light cotton, chambray, or breezy linen that lets your skin breathe and your outfit flow.

Pair them with a flowy camisole, a crochet top, or even a one-piece swimsuit worn as a bodysuit. Add a straw hat, flip-flops or espadrilles, and a tote bag big enough for sunscreen and a paperback. You've just nailed the vacation-core look without even leaving the postcode.

And yes, they also work for post-swim snacks or sunset walks, making them the ultimate multitaskers of the holiday wardrobe. No wrinkled sarongs or wardrobe malfunctions here, just cool, confident vibes.

From Street Style To Staycations: How To Wear Bermuda Shorts Without Looking Frumpy
Photo Credit: Unsplash

7. Edge Things Up With Leather And Statement Accessories

Who said Bermuda shorts had to play nice? If your style leans more rocker than Riviera, there's no reason to ditch your edge. Look for leather or faux leather Bermudas in black or oxblood tones and pair them with an oversized band tee or mesh top.

Layer on some chunky jewellery, a biker jacket, and ankle boots or platform sandals. Suddenly, the same shorts that felt preppy two seconds ago are now full-blown fashion renegades.

This high-low mix adds a streetwear twist to a classic piece, ideal for concerts, late-night cafés, or simply making the pavement your runway. Remember, fashion favours the bold, and Bermuda shorts are more adaptable than they let on.

8. Play With Patterns And Colour Pops

Bermuda shorts don't need to stick to solids to be stylish. When done right, prints and pops of colour can turn your outfit from safe to standout. Think floral, gingham, or abstract designs paired with neutral tops to let the pattern breathe.

Or flip the script, try bright, block-colour Bermudas in coral, teal, or mustard and balance them with a classic white shirt or denim top. It's a quick way to inject some personality without diving headfirst into trend overload.

Patterns also work wonders when the rest of your wardrobe leans neutral. They bring freshness to repeat pieces and spark conversation without screaming for attention. Add a crossbody bag or colourful earrings and let the good vibes roll.

Products Related To This Article

1. Kook N Keech Men Street Style Essential Light Fade Cargo-Style Shorts

2. Kook N Keech Men Everyday Utility Cargo Shorts

3. Glitchez Men Street Touch Below Length Denim Jorts

4. Glitchez Men Un-Plugged Loose Denim Jorts

5. Styli Men Black Oversized Cotton Terry Shorts with Bold Text Print Detail

6. Kook N Keech Men Cargo Shorts

7. DressBerry Women Urban Cool Washed High-Rise Cargo Denim Shorts

8. glitchez Women Flaunting Vibes Typography Print Mid-Rise Loose Fit Shorts

9. LULU & SKY Women Loose Fit High-Rise Shorts

10. glitchez Women Urban Chill Cotton Terry Relaxed Fit Jorts

Gone are the days when Bermuda shorts sat forgotten in the back of the wardrobe, gathering dust and doubt. With the right fit, a dash of styling confidence, and a splash of creativity, they've stepped into the spotlight as one of fashion's most versatile essentials.

Whether you're hitting the high street, lounging on a staycation, or just navigating the unpredictable British weather, Bermuda shorts are your trusty sidekick, comfortable, cool, and far from frumpy. So next time you spot them on the rack, don't walk past them. Give them a second look, throw on your favourite top, and stride out with purpose. After all, style is less about following rules and more about writing your own. Shop now on Myntra.

Disclaimer: The images used in this article are for illustration purpose only. They may not be an exact representation of the products, categories and brands listed in this article.