Which iconic men’s shoe style was once considered the epitome of preppy leisure wear and is now a staple of relaxed summer dressing? You might have guessed it, it’s boat shoes for men. As trends evolve, so do the dilemmas surrounding this classic, from how to wear them to whether they’re still popular in 2026.
How Did Boat Shoes Become a Preppy Summer Staple?
The nautical-meets-collegiate shoe was created 90 years ago by the sailor Paul Sperry after he slipped off his boat, but noticed his dog Prince, whose paws were naturally non-slip, didn’t. A few years after their invention, men’s deck shoes were adopted as the official footwear of the U.S. Navy. And when President John F. Kennedy wore them casually in the 1960s, they cemented their place as a preppy wardrobe, often worn off the boat as a symbol of coastal style, casual sophistication, and summer ease.
Now that we’re in 2026, boat shoes for men are as popular as ever. They are worn in a variety of everyday settings beyond marinas and yacht clubs.
Are Boat Shoes a Must-Have on Deck?
Although not strictly necessary, boat shoes for men are highly recommended for safety and etiquette on deck. With their non-marking, slip-resistant rubber soles, they protect both you and the deck. The upper material (usually leather or canvas) can hold up well against water, salt, and other marine conditions without compromising its integrity.
Many models feature small perforations or drainage channels, allowing water to escape swiftly. This feature ensures your feet stay dry, minimising discomfort and the risk of slipping due to waterlogged shoes.
Traditionally, boat shoes featured a 360-degree lacing system to lock the foot into the shoe, ensuring a firm grip in rough waters. Nowadays, the lacing at the sides and back is decorative and separate from the functional laces.
If your time onboard is minimal and mostly social, they’re not essential, but they still offer a classic and polished look for relaxed summer settings. Plus, their timeless style makes them easy to pair with casual outfits on land.
Do You Wear Them with or Without Socks?
Boat shoes are traditionally worn without socks. However, how you wear them comes down to your personal style and taste. If you have comfort or hygiene concerns, you can wear them with socks, but it pays to get them right. A pair of multicoloured socks can make the outfit appear less mature and clash with the shoe’s traditional, preppy and relaxed style. Black dress socks can make the look too formal, but a pair of no-show or ankle socks is always a smart move.
How to Style Them?
How you style this versatile shoe staple depends on the look that you want to achieve. For a casual look, pair them with tailored shorts that sit just above the knee in neutral colours or classic prints of madras or seersucker. This look works great for weekend activities, summer dinner parties and beach getaways.
If you want to look more formal, pair them with an Oxford shirt and chinos. Brown, classic navy, and burgundy leather boat shoes pair well with olive, navy, khaki, and stone-coloured chinos.
Lightweight linen and cotton pants are another excellent combination for warm weather. These lightweight fabrics can complement the casual tone of boat shoes but are still sophisticated enough for smart-casual occasions. Design-wise, stick to simple patterns that won’t compete with the classic appearance of the shoes.
Denim can work with boat shoes, too. However, you need to give it some thought. Dark straight-leg or slightly tapered-cut jeans work better than baggy or highly distressed ones. The key is to maintain clean lines and avoid overly casual denim that might clash with the clean look of these shoes.
What Are Some Casual Alternatives to Boat Shoes?
Minimal leather sneakers are a versatile alternative to boat shoes. Unlike bulkier sneakers, minimal designs feature clean lines, low profiles, and neutral colours such as white, tan, or navy, making them easy to pair with summer wardrobe staples like shorts, chinos, and casual jeans.
Slip-on canvas shoes are another casual alternative. Lightweight, breathable, and convenient, they are perfect for summer days. Canvas shoes come in a wide range of colours and patterns, from classic neutrals to playful prints, giving you room to express personal style without looking overdone. Although they don’t have the traditional preppy vibe of boat shoes, their simplicity and comfort make them a stylish choice.
Finally, hybrid water shoes are a sporty alternative for those who want practicality alongside casual style. Designed for quick-dry performance, flexible soles, and excellent grip, they are perfect for boating, beach days, and light hiking near water.
Although they look more athletic than preppy, hybrid water shoes protect your feet, provide traction, and dry quickly after exposure to wet surfaces. Many modern designs feature muted colours and sleek lines, making them acceptable for casual outings beyond strictly sporty settings. They pair well with activewear, offering a blend of comfort, safety, and low-maintenance styling.
