Boat Shoes: More Than Just Sailing Footwear

They are a must-have!

Are boat shoes a must-have on deck, do you wear them with or without socks, what makes them special, and why have sea lovers been wearing them on the boat deck and in everyday life for 90 years since they were first made?

They are not sneakers, not loafers, not just for boats, not just for casual outfits… Some call them boat shoes, some deck shoes, some preppy footwear, and some derby chic… In fact, they are a comfortable model of summer shoes with a nostalgic design that is all of that!  

It has been exactly nine decades since passionate yachtsman Paul Sperry made the first boat shoes in New Haven (Connecticut) that remain current without major changes in design and materials to this day. We couldn't help but notice them in the recently aired hit series "Succession," on the Instagram profiles of many fashion girls, on fashion runways, and on the feet of casually dressed men… As their name suggests, boat shoes were created with the idea of being worn on the deck of a boat, to be non-slip and water-resistant.

Below, we bring you the fascinating story of boat shoes: the journey from purely practical (non-slip) footwear to a statement piece of men's and women's shoes worn by all generations.

What defines boat shoes?

1. Boat shoes have a more robust front part, unlike their first "cousin," the moccasin
2. Traditionally, they come with a 360-degree lacing system that ensures a perfect fit to the foot. Models with side laces also provide security when moving on the boat deck, as well as ease of putting on and taking off
3. Unlike other types of footwear, boat shoes are stitched with leather strips, often in white as part of the nautical style
4. Boat shoes have the iconic white rubber sole that leaves no marks and does not slip thanks to the indented grooves that create a unique pattern, most often a herringbone pattern
5. The interior of the shoe is refined with soft insoles and arch supports to reduce foot fatigue and strain.  Given that it is a shoe that has a lot of contact with water, boat shoes are made from quick-drying materials such as canvas and oiled leather.

Sailing Shoes Through Time (and Fashion)

1935. The first sailing shoes

Like all stories about beginnings and great inventive achievements, this one is already legendary – it's a story about a fall into the cold Atlantic, a dog, a man, and a vision. In short, American sailor Paul A. Sperry slipped off the deck of his boat in 1934 and fell into the water. His dog Prince, as Sperry noticed, never slipped - thanks to the grooves on his paws that firmly grip the surface. Inspired by this, he developed the first boat shoe with rubber soles featuring grooves. Thanks to this, sailors and seafarers received a functional and comfortable shoe with non-slip soles, significantly reducing the risk of falls on the slippery deck of a boat. The first Sperry Top-Sider boat shoe was made from medium to dark brown leather upper adorned with leather laces, and the soles were made of white rubber with a herringbone pattern on the insole.

1940. The U.S. Navy

During World War II, the U.S. Navy had a great need for non-slip shoes for sailors. Thus began the large-scale production of Sperry boat shoes. Sailors were thrilled with these comfortable and functional shoes, which they continued to wear after the war as part of their everyday attire. Thus, sailing shoes transitioned from purely functional footwear to fashion items, especially popular among sailors. Alongside Sperry boat shoes, the Sebago shoe company also began producing boat shoes during those years.

1960. The political elite

In the early 1960s, the media was flooded with captivating photographs of the Kennedy family sailing, sunbathing, enjoying the boat with their children, and having a great time. In most pictures, John F. Kennedy and Jackie, as you might guess, were wearing boat shoes. This is considered the beginning of the so-called Preppy style, an aesthetic that first took shape on the campuses of Yale and Princeton and began to spread as an image of a young and casual version of success. Thus, boat shoes became known as attire associated with an advanced, optimistic, and dynamic socioeconomic class.

1980. The preppy style

In the early 1980s, the book „The Official Preppy Handbook” declared boat shoes as one of the key details of the so-called preppy (a term referring to American preparation for elite universities) style of the wealthy elite. The rest is fashion history. Boat shoes became a timeless classic available to everyone: footwear that serves a practical purpose in the lives of sailors and sailing enthusiasts, as well as those who love an elegant, casual style of everyday dressing. During the 1980s, Timberland boat shoes rose to the fashion throne.

Boat footwear since 1990

Boat shoes lost their place on the fashion scene but gained prominence in the nautical world. Numerous brands such as Timberland, Bally, Sebago, Dubarry, Musto, Ralph Lauren, and Loro Piana celebrate nautical adventures with their versions of boat shoes.

Today, boat shoes are a fashion staple

When American influencer, entrepreneur, and model Emma Chamberlain released a video in early 2024 predicting a major comeback of boat shoes on the fashion scene, we couldn't have imagined that these comfortable casual shoes would once again become a fashion statement. Thus, fashion brands like Miu Miu, Fendi, and Loewe "boarded" the trend wave alongside specialized brands for making boat shoes. With the first days of 2025, one of the bigger trends crystallized: the "fisherman" aesthetic in dressing, but also in the general approach to life. Thus, the good old casual style of dressing made a grand entrance, and with it, boat shoes returned to everyday fashion. Boat footwear have been and remain one of the most comfortable shoes, worn – besides on the deck of a boat – to business meetings paired with marine-cut trousers and, say, a striped cotton shirt.