Boat Shoes: Too Preppy Or Still Fashionable?

Boat shoes have been a staple in men's footwear for decades, but their association with preppy fashion has sparked debate. While some view them as a timeless classic, others find them too preppy or even plain bad. This article will explore the history of boat shoes, their role in fashion, and how to style them without looking like a sailor.

Boat shoes, also known as deck shoes or top-siders, were originally designed for boating due to their grip on slippery boat decks. Paul Sperry created the modern boat shoe in the early 1930s, inspired by his dog's ability to grip ice. The shoes gained popularity among sailors and were even adopted by the U.S. Navy. Over time, they transitioned from purely utility wear to a classic piece of footwear for both men and women.

In the 1980s, boat shoes became synonymous with preppy style, particularly after the publication of The Official Preppy Handbook by Lisa Birnbach. This association has endured, with some considering boat shoes a staple in their wardrobe while others find them too stereotypical or exclusive.

Today, boat shoes are experiencing a resurgence, with designers and fashion insiders debating their return. Some attribute this comeback to the 20-year trend cycle, while others note the influence of old money aesthetics and Gen Z's interest in ironic fashion.

For those who want to embrace the boat shoe trend without looking like a sailor, stylists recommend skipping the classics and trying more modern or budget-friendly options. Pairing boat shoes with feminine or masculine outfits that include denim, blazers, and classic preppy pieces can help create a chic look. Additionally, no-show or ankle socks can be worn for comfort without breaking the visual line on the leg.

Boat shoes: too preppy or not too preppy?

Boat shoes have long been associated with preppy style, but opinions vary on whether they are too preppy or not. Some people believe that boat shoes are indeed too preppy and should be avoided if you want to avoid looking like a "beer-bellied" suburban dad. Others argue that boat shoes can be worn in a variety of ways and are a classic, versatile shoe that can be dressed up or down.

The boat shoe, also known as the deck shoe or top-sider, has gone from being purely work/utility wear to becoming a classic piece of footwear for both men and women. The shoe's unique design and construction, with its moccasin-style toe and 360-degree lacing system, make it ideal for boat decks and the perfect footwear for the summer months.

Some people suggest that the key to wearing boat shoes without looking too preppy is to avoid pairing them with nautical-themed clothing, such as striped shirts or pants with nautical button details. Instead, they recommend pairing boat shoes with more feminine or urban outfits, such as a mini skirt and blazer, straight-leg jeans and a button-down shirt, or dark jeans and a t-shirt.

Additionally, the choice of sock can also impact the overall look. Going sockless with boat shoes is a popular option, especially in the summer months. However, no-show socks or ankle socks can also be worn to provide comfort and prevent blisters without breaking the visual line of the leg.

In recent years, boat shoes have been creeping back into fashion, with luxury brands like Miu Miu and Dior offering their own takes on the classic style. This resurgence may be due to the 20-year trend cycle, a nostalgia for old money style, or a desire to reinterpret classic pieces in a more inclusive and less status-focused way.

Ultimately, whether or not boat shoes are considered too preppy may depend on personal style and how they are styled. They can be a versatile and comfortable option for those who want to stay stylish in relaxed settings.

Boat shoes: the perfect summer dress shoe?

Boat shoes have long been associated with preppy style, but are they too preppy? The answer is nuanced. While boat shoes may have originated as utilitarian footwear for sailors and boatmen, they have evolved into a versatile wardrobe staple that can be dressed up or down. With the rise of relaxed dressing, boat shoes have shed their exclusively preppy connotation and are now embraced by a diverse range of individuals seeking comfort and style. So, are boat shoes the perfect summer dress shoe? Let's explore the arguments and some styling tips to pull them off without looking like a sailor.

The Case for Boat Shoes

Boat shoes, also known as deck shoes or top-siders, offer both functionality and fashion. Designed to provide grip on slippery boat decks, they are ideal for casual boating excursions. The distinctive siped soles of boat shoes, inspired by a dog's paw, provide excellent traction on wet surfaces. Additionally, their unlined leather construction ensures comfort and flexibility. Boat shoes are also versatile. They can easily replace your sneakers or loafers and pair well with a variety of outfits, from jeans and a t-shirt to a linen suit or light-wash jeans.

Styling Tips to Avoid Looking Like a Sailor

If you want to embrace the boat shoe trend without channelling a nautical theme, here are some styling tips from fashion experts:

• Skip the classics: Opt for more modern or on-trend variations, such as suede boat shoes with an elongated toe.
• Play with juxtaposition: Try pairing boat shoes with something more feminine to create an interesting contrast.
• Avoid nautical stripes or pants with nautical button details.
• Choose classic, somewhat preppy pieces to create a cohesive look without veering into costume territory.
• Go sockless: Boat shoes are meant for boats, so going sockless makes sense. If you need socks for comfort, opt for no-show or ankle socks.
• Embrace understated trends: When trying out a new trend, it's best to keep it understated. Look for timeless pieces with subtle on-trend details.
• City appropriation: To make boat shoes feel more urban, style them with straight-leg denim, a classic button-down, and a statement belt.
• Edge it up: For a bolder look, pair boat shoes with a mini skirt, a tank top, and an oversized blazer.
• Avoid linen: Instead, gravitate towards cool denim and slightly masculine tops, such as a boxy tee or an oversized blazer.

The Bottom Line

Boat shoes have transcended their preppy origins and are now a classic footwear option for anyone seeking comfort and style during the summer months. By following the styling tips above, you can rock boat shoes without looking like a sailor or falling into the "too preppy" trap. So, are they the perfect summer dress shoe? The answer is yes, as long as you know how to style them to suit your personal taste and lifestyle.

Boat shoes: how to style them without looking like a sailor

Boat shoes are back in style, but how do you wear them without looking like a sailor?

Boat shoes have long been associated with preppy style, but they are now in increasing demand by everyone who wants to stay comfortable and stylish in relaxed settings.

If you're new to the boat shoe trend, stylists recommend skipping the classics and trying a more on-trend option, like a suede shoe with a slightly elongated toe. For those looking for a more budget-friendly option, try a distressed leather offering. Pair any trend with items you know and love and feel comfortable in.

To avoid looking like a sailor, steer clear of nautical stripes or pants with nautical button details. Instead, choose classic, somewhat preppy pieces to give the outfit a cohesive look without feeling like a costume.

When it comes to socks, you can't go wrong by going sockless with a boat shoe—after all, they're meant for boats. But if you need socks for comfort, no-show socks will always work, and ankle socks can look very cool and edgy.

Boat shoes can be worn with straight-leg denim, a classic button-down, and a cool statement belt—the perfect way to make them feel more city-appropriate. For a little more edge, pair them with a mini skirt, tank top, and slightly oversized blazer.

And if you don't want to go too nautical, gravitate towards pairing boat shoes with cool denim and a slightly more masculine top, like a boxy tee tucked into denim or an oversized blazer.

Boat shoes: the best options for those on a budget

Boat shoes have long been associated with a preppy aesthetic, but they are also a practical shoe for seafarers and landlubbers alike. If you're looking for a budget option, there are plenty of choices that won't break the bank. Here are some of the best boat shoes for those on a budget:

Dockers Beacon Boat Shoes

A handsome and classically designed alternative to the OG Sperry. These shoes feature leather uppers, rubber soles, and neutral colors that will pair well with anything from linen button-downs to t-shirts. The best part? They won't make a big impact on your wallet. The only downside is that they have a faux 360-degree lacing system, so if functionality is important to you, you may want to opt for a different pair.

Timberland Classic 2-Eye Boat Shoes

Sturdy, rugged, and classic, these boat shoes are built with comfort in mind. With nearly 4,000 5-star reviews on Amazon and over 70 years of manufacturing experience, these traditional deck shoes will last you for years. While some may not like the prominent logo on the uppers, these shoes are a cozy and well-constructed option.

Sebago Portland Waxed Boat Shoes

Sebago, another pioneer of classic American footwear, offers water-resistant, full-grain leather uppers and linings for cloud-like comfort. The 360-degree lacing system and siped rubber soles provide safety and longevity. These shoes come in a variety of colors, from traditional muted tones to bolder standouts. However, they do have a longer break-in period, and even the wide sizes may not be wide enough for all.

Sperry Bahama II Sneaker

A summer-ready classic, these Sperry boat shoes feature handsome, breathable, and accommodating uppers. If you can get your hands on a pair in white, they'll go perfectly with navy chinos, a braided belt, and a pop of color in your henley or linen button-up. While canvas shoes may not provide enough cushioning for some, this can easily be fixed with a good pair of insoles.

Sail Leather Premium Boat Shoes

Crafted with fine leather, a cushioned footbed, and hand-sewn details, these slip-on wonders are perfect for a ride on the sea or an impromptu stroll by the shore. They are also non-marking and slip-resistant. You can set sail in style and comfort with these budget-friendly boat shoes from Target or Lands' End.

Boat shoes: the best options for those willing to splash the cash

Boat shoes are back in vogue, but how can you wear them without looking like a sailor?

Boat shoes are making a comeback, according to Vogue and The New York Times, but this time it's not about the nautical look. Instead, it's about pairing these classic shoes with chic, contemporary ensembles. So, if you're looking to invest in some boat shoes, here are some tips on how to wear them in style.

Choosing the Right Boat Shoes

If you're new to the boat shoe trend, stylists recommend skipping the classics and opting for a more on-trend option. For example, the Miu Miu suede boat shoe offers a sleek, elongated toe and a lived-in feel that blends old and new. It retails for around $950. For a more budget-friendly option, try the distressed Mango leather boat shoe for $179.

Styling Boat Shoes

When it comes to styling, the key is to pair your boat shoes with items you know and love to create a cohesive look. To avoid looking like a deckhand, steer clear of nautical stripes or pants with nautical button details. Instead, opt for classic, somewhat preppy pieces.

For a unique twist, consider pairing your boat shoes with something more feminine to play with juxtaposition. New York City-based stylist Jordanna Sharp suggests styling boat shoes with straight-leg denim, a classic button-down shirt, and a cool statement belt for a city-appropriate look. For a more edgy approach, pair them with a mini skirt, tank top, and an oversized blazer.

The Great Sock Debate

As for socks, boat shoes are meant for boats, so going sockless is always an option. If you need socks for comfort or to prevent blisters, no-show socks can provide coverage without breaking the visual line on the leg. Ankle socks, similar to those worn with loafers, can also add a cool and edgy touch to your ensemble.

Boat Shoes for All

While boat shoes have been associated with a particular aesthetic, they are versatile and can be styled in various ways. As designer Todd Snyder puts it, "There's always been a bit of that thing, looking in your dad's closet and how you interpret it." So, whether you're going for a classic or contemporary look, boat shoes can be a great addition to your wardrobe if you're willing to splash the cash.

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