Boat Shoes: Back In Vogue Or Sinking Style?

Boat shoes are back in style, but not as you remember them. Once a symbol of wealth and status, these shoes have been reinterpreted through the lens of inclusivity and irony. This time around, they're being styled with wider, pleated shorts, knit polos, camp collar shirts, and ribbed tanks. Boat shoes can even be dressed up with white trousers, a striped tee, and a navy blazer for a nautical cocktail party look.

The resurgence of boat shoes can be traced back to runways such as Miu Miu, Prada, and JW Anderson, as well as their popularity among old money style-obsessed Gen Zs on TikTok. While some still associate them with exclusivity and privilege, others view them as a classic, all-American shoe. Love them or hate them, boat shoes are here to stay.

Boat shoes: a brief history

Boat shoes, also known as deck shoes or top-siders, have gone from being purely work/utility wear to a classic piece of footwear for men and women. They were first created for sailors in the early 1930s by Paul Sperry, an ardent sailor who wanted to solve the problem of slipping on boat decks. He noticed that his dog, a cocker spaniel named Prince, had no trouble running across ice. Upon closer inspection, he noticed tiny grooves in the dog's paws, which gave him grip. Sperry then used a penknife to cut grooves, or "siping", into the rubber soles of his shoes, providing additional traction.

The first of Sperry's shoes, introduced in 1935, had black soles, which left unsightly marks on the boats. To solve this problem, he switched to white rubber soles, and the modern boat shoe was born. Sperry scored a contract with the US Navy to make Top-Siders for sailors, and the shoes became increasingly popular. In 1979, Sperry sold his company to US Rubber, which then passed to Stride Rite.

It wasn't until the 1980s that boat shoes became trendy. They were featured in the influential "The Official Preppy Handbook", and their popularity exploded. They became a staple of East Coast preppy style in the summer, and their appeal spread beyond sailors to non-boaters too. They are now worn by both men and women, and their functionality and aesthetic appeal make them popular casual footwear worldwide.

How to style boat shoes

Boat shoes are back, but how do you style them?

First, a quick history lesson. Boat shoes were originally made for sailors and boaters to prevent slipping on boat decks. But it didn't take long for people outside the boating world to notice their perks, including their practical non-slip rubber sole and unique hand-sewn upper design. Today, they are commonly used by boaters and non-boaters alike, both for functional and aesthetic reasons.

Now, onto the styling tips. Here are some dos and don'ts to help you master the boat shoe look:

Do:

• Wear them to the beach or for other maritime activities.
• Wear them when travelling—they're comfortable and easy to get on and off.
• Wear them to the office, as long as the environment is business casual.
• Wear them on a date—they're a great conversation starter and will show your date a bit of your personality.
• Wear them with jeans. For a more effortless, nautical look, try cuffing the hems of your jeans.
• Wear them with colourful chinos. Just make sure the colour of your pants contrasts with the colour of your boat shoes. For example, pair bold red or green chinos with neutral-coloured shoes.
• Wear them with shorts, especially in the summertime. Again, make sure they balance each other out—pair a detailed, attention-grabbing boat shoe with plainer shorts.
• Wear them without socks or with no-show socks. Visible socks are a big no-no and will make you look like a newbie when it comes to style.
• Wear them with dark wash denim and a blazer for an interesting twist on business casual.

Don't:

• Wear them in the winter. They will look out of place and you risk getting them wet.
• Wear them to a fancy occasion. Boat shoes are meant for more casual and laid-back events.
• Wear them with suits. Boat shoes don't fit this formal look.

So there you have it! Boat shoes are a classic casual shoe option that can be styled in a variety of ways. Just remember to keep the look preppy and effortless, and you'll be good to go.

Boat shoes: fashion do's and don'ts

Boat Shoes: Fashion Dos and Don'ts

The Do's

If you want to style boat shoes, it's important to know the context in which they are appropriate. Boat shoes are a casual shoe, perfect for the beach, travelling, and the office (if it's business casual). They are also a great conversation starter for dates.

When it comes to what to wear them with, boat shoes are very versatile. They can be worn with jeans, colourful chinos, shorts, and suits (although this is more controversial). If you're going for jeans, try cuffing the hems to draw attention to the shoes. For chinos, make sure the colour of your trousers contrasts with the colour of your shoes. For example, if you're wearing red or green chinos, opt for a more neutral-coloured shoe, like brown.

Boat shoes also work well with shorts, but make sure they balance each other out. If your boat shoes are detailed and attention-grabbing, pair them with plainer, more tailored shorts. If you're wearing shorts, it's also recommended to go sockless.

Boat shoes can also be dressed up a bit for a smart casual or even a business casual look. Try pairing them with a white or light blue linen shirt, a tan linen blazer, and dark wash jeans. Cuffing your jeans will also add a nice contrast.

The Don'ts

Boat shoes should not be worn in the winter or to a fancy occasion. They are also not meant to be worn with visible socks, although no-show socks are acceptable.

While boat shoes can be worn with suits, they should not be worn with a full suit. If you want to dress them up, opt for dark wash jeans and a blazer instead.

A Brief History of Boat Shoes

Boat shoes, also known as deck shoes or top-siders, were invented in 1935 by Paul A. Sperry of New Haven, Connecticut, as a utilitarian shoe to maintain one's footing in slippery conditions. They are usually crafted from leather, canvas, or suede and feature a moccasin toe shape.

Over time, they became associated with boat ownership and took on a preppy, ivy-inspired reputation. They were popular among fishermen, yachters, and the country club and prep school crowds. However, they also gained a reputation as a try-hard look, particularly among fraternities, and were often mocked in the 2010s.

Despite this, boat shoes have persisted and are now seeing a resurgence, with fashion houses like Miu Miu, Dior, Fendi, and Prada featuring them on the runway.

Boat shoes: a men's fashion staple?

Boat shoes are back, but did they ever really go out of style?

The classic American shoe invented by Paul A. Sperry in 1935 has been a staple for sailors and the sailing-adjacent for decades. But the boat shoe has also been polarising. Critics have dismissed them as slovenly and a marker of privilege.

However, the boat shoe has been popping up everywhere this season, from the runways of Miu Miu and JW Anderson to fashion houses such as Loro Piana, Saint Laurent, and Dior. Crockett & Jones, a firm not known for chasing trends, has also added a boat shoe to its collection. So, it seems the boat shoe is having a moment.

Veteran designer Todd Snyder says the boat shoe is "forever in". He recently dropped a collaboration with Sperry inspired by the white boat shoes he wore in the '80s. "Whether you consider it cool or not, once you hit classic, you're forever in," he says.

But the boat shoe has also been caught up in a revival of old money style, with its associations of wealth and status. The current resurgence is perhaps rooted in nostalgia, cultural cosplay, and irony.

So, how to wear the boat shoe? Well, it's best to avoid wearing them in winter, and they're not meant for black-tie affairs. But they are perfect for the beach, travelling, the office, and dates. They can be dressed up for a business casual look and work well with jeans, shorts, and chinos. Just make sure to avoid visible socks and don't wear them with suits.

If you want to get on board with the boat shoe trend, there are plenty of brands to choose from, including Sperry, Sebago, G.H. Bass, Ralph Lauren, and Timberland.

So, are boat shoes a men's fashion staple? The fact that they are having a moment in the fashion world suggests they are, but their rich history and longstanding popularity also mean they are here to stay.

Boat shoes: the future of this trend

Boat shoes have been described as long-hated and derided, but it seems that this polarising shoe is making a comeback. So, what does the future hold for this trend?

Boat shoes were originally invented as a utilitarian shoe for boating and deck activities, but they have since become a classic casual shoe in the menswear world. They have been adopted by non-boaters for functional and aesthetic reasons and have been described as "the summer's coolest style".

The boat shoe trend seems to be experiencing a revival, particularly among Gen Z, who are embracing old money style. The resurgence of this trend can be attributed to its appearance on the runways of fashion houses such as Miu Miu, Prada, and JW Anderson. It has also been fuelled by collaborations between veteran designers like Todd Snyder and brands like Sperry, as well as the rise of low-profile shoes in menswear.

The future of the boat shoe trend seems to be moving away from its association with "frat-bros" and towards a more inclusive and ironic interpretation. This shift is reflected in the styling recommendations for boat shoes, which suggest pairing them with wider-legged pants, pleated shorts, or a business casual outfit.

While the boat shoe trend may have had its ups and downs, it seems that it is once again gaining traction and evolving to fit contemporary tastes. So, will this classic shoe continue to rebound, or will it sink back into the depths of fashion history? Only time will tell if this trend has smooth sailing ahead.

Frequently asked questions