Verdict from 97 user reviews

6 reasons to buy

  • Some reviewers claimed that the Sperry Captain’s 2-Eye is constructed with top-notch Sperry quality and craftsmanship.
  • Lots of purchasers appreciated the affordable price of this Sperry shoe.
  • The majority of buyers reported that this shoe fits true to size both in width and length.
  • At least half of the reviewers noticed the moderate arch support of the Captain's 2-Eye.
  • A couple of reviewers stated that they like the style of this Sperry shoe. It is perfect to wear with casual outfits like shorts, according to them.
  • Several colorways of the Captain’s 2-Eye are available.

3 reasons not to buy

  • Although relatively comfortable on foot, several disappointed users commented that the Sperry Captain’s 2-Eye not as comfortable as other Sperry shoes they’ve owned.
  • Several reviewers commented that the interior seams in the heel part rub on their feet when they first wore this Sperry shoe.
  • A couple of wearers felt that the support of the Captain’s 2-Eye shoe is minimal.

Bottom line

Combining a boat shoe’s style with sneakers’ functionality and comfort led to the Sperry Captain’s 2-Eye. Although not as sporty-looking as most lifestyle sneakers, this Sperry low-top’s aesthetic gained approval from most buyers for its style that suits casual outfits.

Aside from being visually pleasing, the Captain's 2-Eye sneakers are built with superior quality and durability. It fits true to size, which is another factor liked by the buyers. However, in terms of comfort, this shoe is claimed by many as not that comfortable because of the stiff heel part.

Tip: see the best sneakers.

Good to know

These low-top sneakers from Sperry Top-Sider is a fusion of boat shoe and sneaker. Buyers have options to cop a pair in sizes ranging from US 4 to 13 in Medium or Standard width. The fit is true to size for most wearers.

The Captain’s 2-Eye from Sperry features a 360-degree lacing system that ensures a secure and personalized fit. While its low-cut structure permits ankle mobility and flexible foot movement, the shoe gives additional support through its cushioned insoles and sturdy rubber outsole.

The original Sperry boat shoe design from 1935 received a makeover with modern comfort through the Sperry Captain’s 2-Eye sneakers. These hybrid low-top kicks feature a sailor-approved appearance and a comfort level of a sneaker. The 360-degree lacing system of a classic boat shoe is utilized, but the upper flaunts a canvas material. Wear these in style with chinos or jeans for a casual look.

While the Captain’s 2-Eye sneaker model follows the design details of a classic boat shoe, its materials nevertheless allow wearers maximum comfort. The upper is constructed with a breathable canvas material instead of the usual leather used on original boat shoes. This hybrid sneaker also features a 360-degree lacing system with rustproof eyelets, which is not common in most sneakers today. Further, the rubber outsole is equipped with the brand’s Wave-Siping technology for superior traction on any surface, wet or dry.

Popularly known for its top-notch boat and deck shoes, Sperry has been in the footwear industry since 1935. It was founded by Paul Sperry, an adventurer and innovator who came from a family of sailors. The first ever Sperry shoe came to life when Paul’s dog Prince gave him the idea of creating a wave siping pattern on rubber outsoles for superior grip even on wet surfaces. This shoe was the Captain's Circular Vamp Oxford or simply Captain's CVO.  

The CVO led to more and more iconic Sperry shoes that the brand eventually expanded its product line to include lifestyle sneakers as well. The Captain’s 2-Eye is released recently to join Sperry's lineup of lifestyle footwear models. It is a hybrid model between a boat shoe and a sneaker. Among its features are canvas upper, 360-degree lacing system, removable insoles, and a rubber outsole equipped with Sperry Wave-Siping technology. Available colorways include Grey, Navy, Navy/Red, and White. Each pair initially retails for about $60.

  • The Sperry Captain's 2-Eye sneakers have removable full-length contoured footbeds for cushioned comfort and abrasion-resistant linings for less break-in period.


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Danny McLoughlin
Danny McLoughlin

Danny McLoughlin is a researcher for RunRepeat covering football, sneakers and running. After graduating with a degree in computer science from The University of Strathclyde, Danny makes sure never to miss a game of his beloved Glasgow Rangers or the Scotland national football team. He has been featured in prestigious publications such as The Washington Post, The Irish Times, Footwear News and the like.