Boat shoes reemerged on the fashion scene after appearing on Miu Miu’s spring 2024 runway and quickly spread to collections from major designers like JW Anderson, Jacquemus, The Row, Burberry and Prada. While the initial hype in early 2024 was mostly confined to the fashion world, recent retail data shows the trend is finally translating into sales: in the first quarter of 2025, boat shoe sales grew by 24 percent year-over-year, marking the category’s first measurable growth in a decade.

In the spring 2025 collections presented during Milan and Paris Fashion Week, top designers like Loewe and Burberry also reimagined this classic silhouette for a new era. The runways showcased boat shoes in updated shapes, unexpected color palettes — including soft pastels, bold reds and vibrant greens — and innovative materials such as soft suede, technical canvas and sustainable leathers.

These modern interpretations featured both traditional moccasin stitching and inventive details like oversized proportions, visible contrast stitching, and color-blocked soles, making boat shoes a versatile staple for both men’s and women’s wardrobes.

The trend’s resurgence signals that boat shoes are now embraced as a stylish, seasonless choice that easily transitions from coastal to city settings. However, the loafer style, also known as deck shoe and top sider, has been around since 1935.

What is the classic boat shoe?

The classic boat shoe features standard elements, including rubber soles with enhanced gripping properties, water-repellent and stain-resistant uppers often made of leather or canvas, a moccasin-like silhouette and thick leather laces. 

Often made from soft leather or canvas, the boat shoe became a preppy-style staple throughout the decades, proving to be a comfortable choice for summertime footwear. Traditionally, boat shoes have brown leather uppers with three or two eyelets and white rubber soles with herringbone patterns carved into them.

The rubber soles are arguably the most distinctive feature of a boat shoe. The soles help prevent slips and falls around wet floors. 

When were boat shoes invented? 

The story reportedly starts with a New Yorker named John F. Sipe. Although his profession is still up for debate — some believe Sipe worked in a slaughterhouse while others describe him as a sailor — the fact is that he would often slip on wet floors due to his job. 

Looking for a solution for his slipping problem, Sipe decided to cut slits in the soles of his shoes. In 1923, he patented his idea. However, Sipe applied his invention to automobile tires and forgot about shoes. 

The sailor and his dog 

A decade after Sipe’s invention was patented, a sailor from Connecticut named Paul Sperry noticed that his dog had no problem walking across the ice on a cold day. According to the brand Sperry, its founder discovered that the cracks on his dog’s paws created a herringbone-like pattern, enhancing his grip. Just like that, he decided to cut paw-like slits into the bottom of his rubber soles, creating the first boat shoe. 

Sperry quickly learned that black-soled shoes could leave marks on boats’ decks. He then started working with white soles to minimize the problem. In 1935, Sperry launched the Top Sider shoe.

Sperry’s first clients were the members of the Cruising Club of America. In 1939, the U.S. War Department ordered Top Sider shoes for each one of its sailors, naming the style as one of the official shoes of the U.S. Navy.

In 1940, Sperry sold his business to the U.S. Rubber Company, which invested in marketing the Top Siders throughout the country. In 1946, the company released new styles of boat shoes.

In the 1960s, John F. Kennedy popularized the preppy summer style. Different brands are still reimagining his New England-inspired wardrobe to this day. JFK was also one of the first celebrities to sport Sperry’s shoes in public.

During that time, Californian surfers also began wearing canvas Sperry shoes to the beach. Later, in the 1980s, “The Official Preppy Handbook,” written by Lisa Birnbach, named Sperry’s boat shoes as an “icon of preppy style.” 

In 1979, the U.S. Rubber Company sold Sperry to the Stride Rite Corporation. In 2007, Payless ShoeSource acquired Sperry and, in 2012, the brand was sold to Wolverine World Wide and Blum Capital Partners. In 2009, Sperry was named the Brand of the Year by Footwear News. 

Are boat shoes still cool?

Boat shoes were always in and out of fashion. Currently, they are experiencing a comeback moment, with many celebrities embracing the style, including Prince Harry, David Beckham, Ryan Reynolds and Andrew Garfield. 

Joining the preppy revival in fashion, Sperry has invested more in collaborations, creating collections in partnership with Rowing Blazers, Brooks Brothers and singer John Legend.

Other brands are also famous for their boat shoe styles, such as Sebago, L.L.Bean, Eastland Shoe and Timberland.

In February 2023, Italian luxury company Loro Piana opened a new factory to meet the “ever-increasing demand” for its footwear, particularly the nautical-inspired White Sole shoes.

Once a symbol of coastal leisure and preppy style, boat shoes have made a remarkable comeback to the fashion spotlight. Their resurgence reflects a broader trend of revisiting and reinventing heritage styles to fit modern tastes and values, blending nostalgia with innovation. Whether worn on deck or downtown, boat shoes now embody a new era of effortless, inclusive style.