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Sperry vs. Sebago vs. Hey Dude vs. Timberland: Which Makes the Best Boat Shoes?

Sperry vs. Sebago vs. Hey Dude vs. Timberland: Which Makes the Best Boat Shoes?

    Good boat shoes can help you stay comfortable and stylish as you do different activities on the boat. The ideal boat shoes also prevent you from slipping or leaving shoe prints on the deck. There are a variety of high-quality boat shoes on the market. They have a lot of similarities with a little differences from each other. When it comes to seaworthy style, Sperry, Sebago, Hey Dude, Timberland are the most recognizable boat shoes brands. They are known for their quality, simple and unique features.Which one is the best? Is Sperry A good shoe brand? Are Sebago shoes good quality? Why are Hey Dudes so popular? What is the difference between Sperry and Sebago? Today, I compare these four boat shoes brand to help you make choice before you buy!



1. Sperry 

Brand History and Origin

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. 

The Sperry Top Sider was designed by Sailor Paul Sperry after he had a terrible fall that almost claimed his life on a boat. In order to proffer a lasting solution Paul Sperry drew inspiration after watching his dog glide through a slippery surface on ice. The Sperry "Top-Sider" boat shoe that was introduced and featured a canvas upper, herringbone siping, and a white outsole to prevent the shoe from leaving dark scuff marks on a boat's deck.  The Commonwealth Shoe and Leather Co. later partnered with Sperry on a design using specially tanned water-resistant leather, which became the familiar Sperry "boat shoe". 

Today the Sperry brand is owned by Wolverine World Wide and is headquartered in Waltham, Massachusetts. Since 2021, Sperry has opened 2 specialty stores and 40 outlet stores across the United States.


Sperry Men's Authentic Original Boat Shoes

The one that started it all, the Authentic Original Boat Shoe is a tried-and-true icon of prep style. True to heritage, they' re still hand-sewn using time-honored craftsmanship, with premium materials and the wet/dry traction that made them legendary. Effortlessly setting the bar for what a real boat shoe should be, seafarers love the A/O's capability; street-farers crave its classic cool.

Official Price: $94.95

Colors: sahara leather, tan, oatmeal, amaretto, black, brown buck, classic brown




  • Sperry's most iconic silhouette, inspired by the sea and made for all walks of life.

  • Full-grain leathers and moccasin construction feature rawhide laces and rust-proof eyelets with  360° Lacing System™ for a customized fit.

  • Ortholite® cushioning ensures all-day comfort, while a non-marking rubber outsole features signature Sperry Razor-Cut Wave-Siping™ for ultimate wet/dry traction.

  • Genuine hand-sewn moccasin construction conforms to your foot for durable, broken-in comfort.

  • Lightweight and highly flexible.

  • The 2 eye boat designs makes it stand out among other shoes. In recent times , the sperry boat shoe is being destined to fit in to the contemporary style trend for men.

  • With nearly 30 options to choose from, you’re bound to find a top-sider catered to your taste. Remember that a Sperry shoe will often stretch a wee bit.


  • The actual shoe color is lighter than the one displayed on the website

  • It requires some break-in time as most boat shoes do.

Where to Buy Sperry Shoes for the Cheapest? (5-7% cashback) (5.5-7% cashback)

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2. Sebago 

Brand History and Origin

Sebago is an American Maine-based company creating boating and deck shoes, as well as dress shoes. Sebago was founded in 1946. An owner of five independent shoe stores in Maine was determined to keep his stores stocked. So, in the true spirit of New England ingenuity he partnered with two local businessmen and created a handsewn footwear factory. 

With avid sailors running Sebago in the late 60's, they looked to create a functional, handsewn leather boat shoe. The Docksides was launched in 1970 to meet that need, and has grown to historic status. Shortly after that, Sebago expanded to the production of women docksides which has been making waves locally and internationally. It is still being handsewn and finished the same way but new materials and colors have evolved the Docksides to casual shoe status. 

During the 1980s, the Sebago "Docksides" become a fashion trend at universities and high schools across the United States, as it was mentioned in The Official Preppy Handbook. In 2017, BasicNet acquired Sebago from Wolverine World Wide.


Sebago Docksides Boat Shoes

Constructed to be the perfect nautical footwear, these long-lasting boat shoes are made of a unique piece of unlined full-grain leather,  pull-up leather,  or soft and comfortable suede and hand-sewn with the finest craftsmanship.

Official Price: $150-$215

Colors: Blue Navy, Blue-Petrol-Violet-Mustard, Indigo, Blue Tones, Blue Navy - Brown Dk Ocra, YellowGold-Cognac-White, GSage-Taupe-Camel, Navy-DkGrey-MdGrey, Dk Red,  Beige Taffy, etc.




  • Sebago docksides is a nautical footwear. Boasting that classic deck shoe look that never goes out of style,  it features moccasin construction.

  • Handsewn moc construction is beautifully complemented by an around-the-collar rawhide lacing.

  • Non corrosive brass eyelets, and  leather sock lining.

  • The moc toe stitching is beautifully complemented by an around-the-collar rawhide lacing.

  • 360° rawhide lace system and non-marking antislip siped rubber soles to offer stable grip in all weather conditions.

  • Made with unlined full grain leather.

  • Unique Leather sock lining.

  • Non marking anti slip rubber soles for balance.

  • New materials and colors have evolved the Docksides to casual shoe status. Sebago docksides fits into field and office use. 

Cons: It requires some break-in time as most boat shoes do.

Where to Buy Sebago Shoes for the Cheapest? (10-12% cashback) (1.5-2% cashback)

3. Hey Dude 

Brand History and Origin

Hey Dudeis an Italian footwear company established in 2008 by Alessandro and Dario in the city of Florence, Italy. The concept of the company was to create and design shoes that looked like contemporary, modern shoes, whilst offering the comfort of slippers. 

By February of 2009, the first Hey Dude shoe had reached the market, after only a year the company was successful enough to open a Branch in the USA, opened up by new member to the team, Daniele.

In June of 2010, Dude was being stocked across the whole world, by expanding markets across Europe and into eastern Asia and south America. By October 2011 - just over 30 months since the company was founded – Hey Dude shoes had sold 1 million pairs, showing the explosive popularity of the lightweight, comfortable, stylish and affordable shoes.

Hey Dude Wally is the most popular style. In 2018 Wendy, the women's version of the ever-popular Wally shoe had been produced and in August 2018 5 million pairs of Hey Dude shoes had been sold.


Source:Hey Dude ins

Hey Dude Wally Sox Classic Shoes

Famed for their comfort and light weight feel, Hey Dude shoes are recognised as one of the top 10 best selling shoe based purchases on internet buying site Amazon.  Hey Dude Shoes are not made to be worn in the water. They are made to be worn as regular shoes, and they come in a variety of colors and styles that are perfect for everyday wear. 

Official Price: $59.95

Colors: Ash, Charcoal, Beige, Jet Black, Brown, Meteorite, Blue, Tobacco, Black. Fog, Came, etc.




  • Flex & Fold Technology.

  • Bi-component stretch-knit upper.

  • Stretch-cotton lining.

  • Easy-On System with elastic laces.

  • UltraLIGHT Outsole -The soles are very soft and flexible, which makes them easy to walk around in.

  • Ergonomic, leather-lined, removable memory-foam insole - The inside of the shoe is also very smooth and soft, which makes it very comfortable on your feet.

  • Machine washable (cold), Air dry.


  • Get dirty easily.

Where to Buy Hey Dude Shoes for the Cheapest? (4-6% cashback)

4. Timberland

Brand History and Origin

Timberland  is an American manufacturer and retailer of outdoors wear, with a focus on footwear, which is often known colloquially as "Timbs." It is owned by VF Corporation.Having introduced the innovative injection-moulding technology to the manufacturing of footwear in the 1960s, Abington Shoe Company revolutionised the industry by creating the first high-quality, mass-produced waterproof boots. The footwear was formally designed as a work shoe not until 1979 when the Timberland company decided to build casual boat shoes.

The newly named Timberland Company increased its product line to include casual shoes, eventually expanding internationally. Now, Timberland shoes are being patronized by hikers in the world, known as one of the best hiking boots globally. While the boots are good for hiking the timberland boat shoes can serve as sporty shoes meant for long walk, leisure strolls, for racing, yacht shoes, office shoes and so on.


Timberland Men's Classic 2-EYE Boat Shoes

Whether lounging on the deck of a boat or strolling through town, you’ll be in perfect nautical style with the Timberland Men's Classic 2-Eye Boat Shoe. Industry-leader when it comes to high-quality outdoor wear, their line of casual boat shoes is a true reflection of the craftsmanship, comfort, and durability Timberland became known for. 

Official Price: $95

Colors: Root Beer, Dark Brown, Navy




  • Full grain and nubuck leather uppers.

  • Better Leather from a tannery rated silver for its water, energy, and waste management practices.

  • Full-length EVA-blend foam insert with an additional layer of Poron® foam under the forefoot.

  • It features hand-sewn premium full-grain and nubuck leather uppers, a foam EVA insert for added comfort and support.

  • A 360° rawhide lacing system for a custom fit, and grippy rubber outsoles for maximum traction on slippery and wet surfaces.

  • Siped rubber outsole.

  • Timberland boat shoe ensures comfort and durability.


  • It requires some break-in time as most boat shoes do.

  • Lack of colors and styles.

Where to Buy Timberland Shoes for the Cheapest? (4-5% cashback) cashback)

  • Conclusion

Sperry vs. Sebago vs. Hey Dude vs. Timberland: which makes the best boat shoes?

1) From the above, we can see that sperry, sebago and timberland docksides have a lot in common. They have nice designs that tie in with different outfits, so it is up to you to choose. Comfort is another name for these dockside, used in all weather conditions both o fits into field and office use n land, boat and ship. 

2) Sebago, Sperry and Timberland are all nautical shoes made of strong leather, with slitted sole grooves to ensure balance. The difference is that some Timberland boat shoes built a bit higher than Sperry and Sebago docksides. And Hey Dude is much more different in material.

3) In terms of color selection in the Sebago Docksides vs Sperry Topsiders vs Timberland boat shoes battle, the Sperry brand offers a wider range. If you want a pop of color, then the Sperry brand is the way to go and if you want neutral colors, Sebago and Timberland are your choice.

4) Hey Dude shoes are particularly popular in the United States, particularly with middle school and high school students to wear during the school day. They are made to be worn as regular shoes, and they come in a variety of colors and styles that are perfect for everyday wear.

5) Due to the use of quality leather, good traction soles, and an appealing design, Sebago is among the best boating shoes in the market. The might take a while to break in but the durability of the shoes is commendable.

I'm sure you have found the one that you want after seeing these reviews! Sign up at Extrabux, then you can enjoy up to 12% cashback on your order! 

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2022-06-07 18:285644