Preppy Style’s Return Calls For Sperry Boat Shoes (2024)

FAQs

Are boat shoes preppy? ›

“I think we are seeing a return to preppy,” explained Matt Powell, an advisor at Spurwink River consultancy. “And boat shoes are the epitome of preppy.”

Fast-forward to today, and the preppy trend is making quite the resurgence in the fashion scene. And of course, the style set is hopping on the wave quickly with pieces like pleated miniskirts, polo shirts, and—yep, you guessed it—Sperry boat shoes.

Are boat shoes in style? For sure! If you're looking for timeless shoes that are perfect for adding to a capsule wardrobe, then these are a no-brainer. A summer wardrobe staple for many men, boat shoes stay on trend year after year thanks to their versatility, comfort and style.

Sperry Shoes Are Originals

Their hand-sewn Tru-Moc, full-leather construction makes them a more stylish alternative to canvas sneakers or your regular walking shoes.

Color. Boat shoes come in a wide variety of colors these days, but it's best to go with a darker brown. It's the most handsome, classic, and versatile color and will go with nearly everything.

Boat shoes are designed to be comfy and airy without socks, and most people keep their ankles bare for the classic maritime look – preferably with no-show socks. If you're going for an 80s preppy look, however, socks and boat shoes are definitely part of the uniform.

Cons: They look like sneakers, support your foot, and feel like sneakers. You might even be tempted to go for a run in them. Don't. The hard bottom, which provides the traction, doesn't give your foot much flex, meaning blisters are bound to appear.

Looking for the short answer? Yes, you should wear socks with Sperrys. For enhanced comfort, your personal health (more on this below) and to extend the life of your shoes, it is recommended to wear socks with Sperrys.

Sperry ceased to exist in 1986 following a prolonged hostile takeover bid engineered by Burroughs Corporation, which merged the combined operation under the new name Unisys. Some of Sperry's former divisions became part of Honeywell, Lockheed Martin, Raytheon Technologies, and Northrop Grumman.

Unlike many casual shoes, Sperry Topsiders have mostly unlined leather uppers with minimal seaming and and leather sockliners, which means it is reasonably comfortable to wear them without socks, and they will not immediately begin to smell skan*y. Especially in warm weather, that is very desirable.

Do you wear dress socks with boat shoes? ›

Wearing dress socks with boat shoes will provide a slightly more formal look while still staying relaxed and casual. Beyond no-shows and dress socks, there really are not any other styles of sock that can appropriately be worn with boat shoes. Under no circ*mstances should you wear athletic socks with boat shoes.

In the 1980s through to the early 1990s, they became a fashion trend and returned in 2007–2008 and the 2010s. They were worn with every day and dress wear by boys, girls, men and women. The fashion was widely popular from upper elementary to college age in many countries.

No, in fact, Sperry boat shoes tend to run big, specifically in terms of length. Sperry top-siders are usually roomier in the part of the heel but true to size in the forefoot for average wearers.

But for some of us, loafers and Sperrys never seem to "break in", and they slip and/or rub blisters onto our heels every single time we wear them. Either our feet don't develop thick enough calluses to protect our skin, or the shoes simply aren't able to conform to our feet.

These non-marking rubber-soled shoes are used for wet conditions, making it easier to find grip on a slippery deck. The rubber tread is cut in a siping pattern, which means it has small grooves cut across larger tread elements, similar to tires.

Since boat shoes are ideal for warm weather, they look great with a pair of shorts. You can dress them up by wearing a pair of shorts with a button-up shirt. For a more casual look, wear them with a tank top or T-shirt.

The 'Classic Evening Gent'

It's no secret that the boat shoe is more of a casual lifestyle form of footwear. It's made to last and to be put through the tests of life on board a boat, but when the evening comes and you're more relaxed, this shoe really offers a second aspect perfect for evening attire.

A boat shoe is also appropriate, especially if the wedding is beach-bound; they will look great with tailored chinos. Suede driving shoes are also a popular option, as they're stylish and comfortable, and instantly elevate any smart-casual look.

You Plan on Hiking - Boat shoes are just fine for walking the piers and streets of town. Or the back yard or office for that matter. But under no circ*mstances should these shoes be used for hiking out in the woods or in rocky terrain. While boat shoes have ok traction, the traction isnn't ideal for hiking.

Don't… Wear them in the winter: Not only do you risk them getting wet, but they will look out of place. Save them for the warmer environment they were made for. Wear them for a fancy occasion: Boat shoes are not meant for black tie affairs.

Can you wear Sperrys with dresses? ›

While you may know them for their classic “boat shoes”, they have so many styles available for women, men and kiddos! As you can see, a pair of Sperry's can be worn with just about anything from casual denim to feminine dresses + skirts!

These are a classic, and perfect for walking. Sperry boat shoes are made of high quality leather and great for slipping on without socks. They have a padded foot bed and water resistant finish to keep you comfortable.

If your office has a smart casual dress code, then do your feet a favor with a pair of Sperry leather sneakers—some of the best sneakers for standing all day.

While Sperrys aren't technically waterproof, they are water-friendly and it's more than OK to get them wet (they were created for slippery boat decks, after all). Your Sperrys can handle water and will eventually dry, with a patina that looks even better than they did pre-soak (in our humble opinion).

When sweat gets trapped inside your shoes, bacteria begin to form in the moist environment, which can result in an odor. The trick to fresh feet is keeping your shoes free of moisture by using antiperspirant, powder and letting your shoes dry properly after each wear.

Arrived on time and fit exactly as expected. Very durable, long lasting casual shoe to wear with shorts or jeans. I've owned Sperry Topsiders for 50 years. They're long lasting and durable, and look good whether you are on a boat sailing, striding through a park in your shorts, or walking through an airport in jeans.

Leather will stretch over time. If the boat shoes are made of synthetic materials, stay true to size—these won't stretch, as they're constructed to hold their shape. Keep in mind, the break-in of your new boat shoes will only affect the width (not the length).

Sperry or Sperry Top-Sider is an American brand of boat shoe designed in 1935 by Paul A. Sperry. Sperrys, or Top-Siders, were the first boat shoes introduced into the boating and footwear markets.

Subject to the exclusions and limitations detailed below, Sperry Instruments provides a limited lifetime warranty on products of its manufacture will be free from defects in materials and workmanship under normal use and service.

What does Sperry stand for? ›

a person who uses scientific knowledge to solve practical problems. artificer, discoverer, inventor.

Performance is always important in a quality boat shoe, but you don't have to sacrifice comfort and looks with these boating shoes. This Sperry Authentic Original is made out of rich genuine Sahara Leather, with a color-contrasting outsole, so they will look good even on dry land.

It does not use fur, wool, down, exotic animal skin or exotic animal hair. It uses leather. Sperry is rated 'Not good enough' based on information from our own research.

These water-resistant styles are ready to take you anywhere no matter what the weather brings. They'll keep your feet dry, warm, all-while keeping your style on point.

First up, boat shoes look great on men when paired with jeans, chinos or shorts. For women, these shoes work well with cropped or cuffed denim but also can be worn with skirts, casual dresses, shorts and khakis, too.

It would be a wise choice to opt for a plain t-shirt, paired with some denim jeans and, of course, your boat shoes. Remember to avoid bold print t shirts as this doesn't generally suit the style of the shoe.

Deck Shoe Characteristics

They traditionally feature a 360° lacing system. This gives the wearer the ability to clinch the shoe's collar for better security on the foot. The laces are made from the same material as the uppers (leather). Leather uppers are treated to repel water and to be stain proof.

Paul Alling Sperry (December 4, 1895 – November 7, 1982) was an American inventor, businessman, photographer, screen printer, sailor and outdoorsman. He designed the first boat shoe and founded Sperry (formerly Sperry Top-Sider), a sportswear company now headquartered in Waltham, Massachusetts.

Yes, Sperry's shoes are business casual.

Originally designed as boat shoes for deckhands, the brand Sperry has evolved its shoes to incorporate many styles, most of which would be considered business casual.

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What makes boat shoes different? ›

Boat shoes are a cousin of the men's loafer, but with one big difference: laces. Boat shoes, also known as deck shoes, top-siders or sailor shoes, often have 360-degree laces, where the laces actually thread around the heel of the shoe.

Sperrys are one of the most trusted and widely-worn brands of boat shoes in the world. Since they're built for boating, a little water won't hurt them, and they'll usually air dry just fine on their own in 12-24 hours.

Unfortunately, they're not as simple as your average sneaker, and they require a bit of work to break in and keep clean.

You can purchase the shoes with a white sole to prevent scuffing and marking up the boat. Maintaining a clean boat is good for the environment, safety, and longevity of the boat. Shoes with darker soles tend to leave visible marks on the deck, which means more work to keep it clean.

Rinse the soles out well and let them air dry, not exposed to any heat to avoid shrivelling. Replace and make sure you deodorize them often. These shoes are NOT designed to go into the washing machine, so take good care of them and you'll have your Sperry shoes last you for years.

Avoid wearing them with formal attire.

Boat shoes pair well with semi-formal outfits, such as a pair of slacks and a blazer. They do not, however, pair well with a tuxedo. Choose a lightweight loafer if you are looking for a shoe to wear for a summer wedding or other formal occasion.

In 1935, Paul Sperry, invented the modern boat shoe to offer a new option to those who enjoy the open seas. These non-marking rubber-soled shoes are used for wet conditions, making it easier to find grip on a slippery deck.

Wear them to the office: As long as you work in a business casual environment, boat shoes are more than appropriate. They add some style to your outfit without going overboard. Wear them on a date: Wearing a pair of boat shoes is not only a great conversation starter, but will show your lady a bit of your personality.

Today, this mid-height outdoor boot originally developed by L.L. Bean for hunting has grown past its practical origins into a preppy staple.

Looking for the short answer? Yes, you should wear socks with Sperrys. For enhanced comfort, your personal health (more on this below) and to extend the life of your shoes, it is recommended to wear socks with Sperrys.

Can I wear sperrys for business casual? ›

Yes, Sperry's shoes are business casual.

Originally designed as boat shoes for deckhands, the brand Sperry has evolved its shoes to incorporate many styles, most of which would be considered business casual. Here are some of the different kinds of Sperry's shoes that are considered business casual: Boat shoes.

Boat shoes (also known as deck shoes) are typically canvas or leather with non-marking rubber soles designed for use on a boat.

Rain, sleet, snow—they're all manageable conditions as long as you have the right all-weather shoes on hand. That's why we always stock Sperry's no-slip boots in our closet. Not only can these shoes manage any terrain—everything from a snowy mountaintop to a slick parking lot—but they're easy to style.

Sperry boots don't just work well in the damper, cooler environment of fall. As the season changes into winter, you'll find they're also comfortable to wear in the snow. There are many different styles and colors, making them perfect for the cool fall weather, snowy winter weather, and even the wet spring weather.

The best part of duck boots is that they can be worn whether you're trekking through snow or puddles on a rainy day. They're waterproof, so no snow or rain will get your socks wet, and some are even flannel-lined, making them even more ideal for a snowy day.

Fashion. Bean Boots are considered to be part of prep fashion due to their classic design and use at elite prep schools in New England.