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Shoes Men's Casual

Best Men's Sperry Boat Shoes

Jennifer Manfrin
Written by Jennifer Manfrin

Jennifer has a decade-plus of experience testing the best products on the market, leading her neighbors to ask if she ever stops vacuuming.

Updated March 2024
Bottom line
Pros
Cons
Best of the Best
Sperry Gold A/O 2-Eye
Sperry
Gold A/O 2-Eye
Customer Favorite

In spite of a few minor issues, these Sperrys are off the charts when it comes to handsome style, lasting quality, and superb comfort once you break them in.

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Customer Favorite
Bottom Line

In spite of a few minor issues, these Sperrys are off the charts when it comes to handsome style, lasting quality, and superb comfort once you break them in.

Pros

Garners praise for stylish looks, durable structure, precise cushioning, reliable traction, and extended-wear comfort. Leather feels supple. Versatile look for dressy and dress down occasions.

Cons

Expensive for Sperry. Not very breathable. Breaking them in may take a while.

Best Bang for the Buck
Sperry Bahama II Boat Washed Sneaker
Sperry
Bahama II Boat Washed Sneaker
Bargain Pick

A must-have for men who love the looks of Sperry and sneakers, as this pair combines the best of both for a price that's a bit lower than most shoes by the brand.

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Bargain Pick
Bottom Line

A must-have for men who love the looks of Sperry and sneakers, as this pair combines the best of both for a price that's a bit lower than most shoes by the brand.

Pros

Lightweight. Attractive boat sneaker. Ideal for warm weather. Textile and canvass construction offers breathable comfort. Ideal for casual wear.

Cons

Sizes run somewhat narrow. May fit tightly on wide feet. Not the best choice for dressy events.

Sperry Billfish 3-Eye Boat Shoe
Sperry
Billfish 3-Eye Boat Shoe
Most Stylish

Whether your are boating, fishing, or dressing for a casual dinner, these traditional boat shoes are comfortable for extended wear and fashionable for many summer-inspired activities.

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Most Stylish
Bottom Line

Whether your are boating, fishing, or dressing for a casual dinner, these traditional boat shoes are comfortable for extended wear and fashionable for many summer-inspired activities.

Pros

Classic boat shoe look. Durable leather. Breathable mesh upper panels, mid-sole and tongue padding – features that equal both style and comfort. Short break-in period.

Cons

Size runs narrow on some men. Likely to require a break-in period.

Sperry Authentic Original
Sperry
Authentic Original
Classic Design

If you are looking for classic topsiders, this is the pair to get – they are easy to slip on, comfortable to wear, and come in several color combinations that look great with almost any warm-weather or nautical style.

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Classic Design
Bottom Line

If you are looking for classic topsiders, this is the pair to get – they are easy to slip on, comfortable to wear, and come in several color combinations that look great with almost any warm-weather or nautical style.

Pros

One of the more classic pair of boat shoes by the brand. Complements most warm-weather attire from casual to dressy. Leather construction earns praise for all-day comfort and longevity.

Cons

Runs large. May rub and cause a few blisters during the short break-in period. Blisters and rubbing occurs more if worn without socks like most men prefer.

Sperry Mako 2-Eye Canoe Moc
Sperry
Mako 2-Eye Canoe Moc
Simple Yet Solid

Choose these boat shoes if you prefer a style and build that's a bit more substantial – an ideal shoe for extending your summer activities into the autumn months.

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Simple Yet Solid
Bottom Line

Choose these boat shoes if you prefer a style and build that's a bit more substantial – an ideal shoe for extending your summer activities into the autumn months.

Pros

More structure than comparable topsiders. Combination of padded foot bed, interior cushioning, and dual-density bottom provides excellent support. Versatile for casual and dressy wear.

Cons

Leather isn't as soft or breathable as some others in the Sperry family. Feel somewhat stiff. Some owners gripe about the leather dye rubbing off on socks. Size discrepancies – may run too small or too large.

Why trust BestReviews?
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We only make money if you purchase a product through our links, and all opinions about the products are our own. About BestReviews  
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We only make money if you purchase a product through our links, and all opinions about the products are our own. About BestReviews  
BestReviews spends thousands of hours researching, analyzing, and testing products to recommend the best picks for most consumers. We buy all products with our own funds, and we never accept free products from manufacturers.About BestReviews 
HOW WE TESTED

We recommend these products based on an intensive research process that's designed to cut through the noise and find the top products in this space. Guided by experts, we spend hours looking into the factors that matter, to bring you these selections.

Click here for testing insights
First Reviewed
January 20, 2022
33
Models
considered
8
Hours
researched
Category cover
The team that worked on this review
Our Top Picks
Sperry
Best of the Best
Sperry
Gold A/O 2-Eye
Bottom Line
In spite of a few minor issues, these Sperrys are off the charts when it comes to handsome style, lasting quality, and superb comfort once you break them in.
Shop Now
Sperry
Best Bang for the Buck
Sperry
Bahama II Boat Washed Sneaker
Bottom Line
A must-have for men who love the looks of Sperry and sneakers, as this pair combines the best of both for a price that's a bit lower than most shoes by the brand.
Shop Now
Sperry
Top Pick
Sperry
Billfish 3-Eye Boat Shoe
Bottom Line
Whether your are boating, fishing, or dressing for a casual dinner, these traditional boat shoes are comfortable for extended wear and fashionable for many summer-inspired activities.
Shop Now
Sperry
Top Pick
Sperry
Authentic Original
Bottom Line
If you are looking for classic topsiders, this is the pair to get – they are easy to slip on, comfortable to wear, and come in several color combinations that look great with almost any warm-weather or nautical style.
Shop Now
Sperry
Top Pick
Sperry
Mako 2-Eye Canoe Moc
Bottom Line
Choose these boat shoes if you prefer a style and build that's a bit more substantial – an ideal shoe for extending your summer activities into the autumn months.
Shop Now
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