Bermuda shorts have officially made their comeback—and this time, they’re not just for your dad on vacation. Sleek, tailored, and surprisingly versatile, the 2025 version of Bermudas is all about elevated ease. Whether you’re pairing them with an oversized blazer, a crisp tank, or even a leather jacket, the key to making this trend feel modern (not awkward) comes down to one often-overlooked detail: the shoes.
Yes, the wrong footwear can throw the whole vibe off—too chunky, too flat, too casual—and suddenly you’re giving “lost tourist” instead of “cool girl on the move.” But the right pair? That’s where the magic happens.
In this guide, we’re breaking down exactly what shoes to wear with Bermuda shorts to keep your outfit feeling intentional, current, and effortlessly chic—from kitten heels to sporty sandals and everything in between. Let’s style it out from the ankles up.
1. With Printed Ballet Flats
This look is proof that Bermuda shorts can be boardroom-appropriate without sacrificing style. The structured khaki Bermuda shorts are sharply tailored and paired with a crisp white button-down—classic, clean, and elevated. But it’s the snake-print loafers that bring the fashion-forward edge, anchoring the outfit with personality and polish.
The bold yet refined choice of footwear adds just enough texture and print to break up the minimalism, while still feeling completely intentional. A tan top-handle bag and oversized frames finish the look with authority, giving off “CEO on-the-go” energy. This pairing shows that when styled right, flat shoes with Bermudas can look luxe—not lazy.
2. With Pointed-Toe Pumps
This look is a masterclass in high-low styling—and the pointed-toe pumps are doing all the heavy lifting. Paired with frayed, light-wash denim Bermuda shorts, these sleek cream-colored heels add unexpected elegance and structure to an otherwise casual piece.
The dramatic, tailored blazer and oversized flower pin push the outfit into fashion-editor territory, but it’s the shoes that seal the deal—elongating the legs and creating a streamlined silhouette. The contrast between sharp heels and laid-back denim gives the outfit just the right dose of tension and cool. If you’re dressing up Bermuda shorts in 2025, pointed-toe pumps are a power move.
3. With Heeled Mules
This look is peak minimalist sophistication—with just the right amount of sultry polish. The tailored dark charcoal Bermuda shorts are smart and structured, creating a strong foundation for the relaxed tucked-in blue button-down. But it’s the brown heeled mules that really elevate the entire outfit—literally and stylistically.
The open-toe design keeps things breezy, while the heel gives height and confidence without competing with the tailored silhouette. Perfect for drinks, dinners, or a dressed-up day in the city, mules bring the soft femininity that tailored Bermudas love. In 2025, this shoe pairing proves you can do powerful and pretty in one step.
4. With Kitten Heels
This outfit nails the balance between prim and playful, and the burgundy kitten heels are the unsung heroes. The classic khaki pleated Bermuda shorts are styled with a voluminous, retro-inspired blouse featuring a dramatic sailor collar, giving the look a nod to vintage elegance.
Enter the patent leather kitten heels—pointed, strappy, and rich in color—which ground the outfit with a feminine, fashion-forward edge. The heels add just the right amount of height without taking away from the ease of the shorts, making this an elevated daytime option that doesn’t feel try-hard. This is how you do statement styling in 2025: crisp, clever, and carried by the right shoes.
5. With Strappy Sandals
This all-cream Bermuda short suit is effortlessly chic—but it’s the strappy heeled sandals that give it that editorial punch. The tailored ensemble, featuring a boxy blazer and knee-length shorts, walks the line between masculine and feminine, so the delicate crisscross straps of the heels are the perfect contrast.
They add structure and sensuality, softening the sharper tailoring while keeping the look light and summer-ready. The tonal matching makes the legs look even longer, enhancing the clean lines of the outfit. In 2025, this is how you do head-to-toe tailoring without feeling too buttoned-up: let your shoes add the vibe shift.
6. With Minimalist Heels
This look is the epitome of modern minimalism—and the black minimalist heeled sandals are what tie it all together. The neutral belted Bermuda shorts and matching structured blouse bring a utilitarian edge, softened by clean lines and monochrome ease.
Enter the delicate, barely-there sandals: they balance the longer hemline without adding bulk and instantly make the look feel more elevated and intentional. The small heel offers just enough height to lengthen the leg, while still keeping it daytime-appropriate. Paired with oversized sunnies and a suede tote, this outfit says “I don’t try hard, I just know what works.”
7. With Over-the-Knee Boots
Forget everything you thought you knew about Bermuda shorts—this look flips the script. The faded, frayed denim shorts are intentionally oversized and paired with an equally relaxed white button-down, creating an ultra-casual base. But then come the structured black knee-high boots, and suddenly the whole outfit shifts from basic to editorial.
The boots add drama, edge, and a sleek vertical line that balances out the boxy silhouette. Topped with oversized shades and a delicate neck flower, this pairing is not just about following trends—it’s about setting them. For fall layering or fashion-week vibes, tall boots with Bermudas are pure power styling.