We spent 6.5 hours reading reviews from experts and users. In summary, this is what sneaker fanatics think:

8 reasons to buy

  • Heaps of shoppers have raved about the Sperry Sailor’s super level of comfy.
  • The pair is very budget-friendly.
  • Lots of users say they can wear the shoe all day long without hurting their feet.
  • Many customers express that the Sperry Sailor looked absolutely cute.
  • The use of colorful satin ribbon laces as shoe strings has delighted plenty of women.
  • More than a couple of reviewers recommend the Sperry Sailor.
  • Several women share about getting compliments whenever they put on the shoe.
  • An ample amount of wearers have noted that the Sperry Sailor matches well with many outfits.

3 reasons not to buy

  • Some users find the pointy toe box a bit narrow.
  • The shoe’s bottom feels very flat before they’re broken in, according to a few users.
  • At least one user has expressed having trouble keeping the leather upper clean.

Bottom line

With its slim, low profile, pointy toe box, and satin ribbon laces, the Sperry Sailor showcases a cute and chic look, which a lot of women liked. However, it was the shoe’s superb comfort that has collected the most number of positive feedbacks from its users.

Sperry offers the sneaker at a budget-friendly price. Packed with great overall features, the Sperry Sailor proves to be good, wise purchase.



A top rated sneaker
A top rated Sperry sneaker
It has never been more popular than this May

Expert Reviews

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The Sperry women’s Sailor Shoe has a low-top profile that gives the ankles more freedom of movement. A 360-degree saddle lacing system, run by satin laces, locks the feet in with custom fitting.

Looking smart, sophisticated, and laidback at the same time, the Sperry Sailor can be easily dressed up and down. Women can pair this shoe with bright-colored loose-fit jeans paired with a sleeveless shirt wrapped in a washed-blue cardigan. Then top it off with a hat or cap of choice for that casual springy or summery look. For semi-formal wear, the Sperry Sailor also compliments shorts, skirts, and dresses all too well.

The Sperry Sailor is offered in a small variety of plain colorways, in Grey, Ivory, Lilac, and Mint.

The Sperry Sailor Boat Shoe has a soft pastel nubuck upper, which is secured by a 360-degree lacing system with ribbon satin laces. Its non-marking rubber outsole has the famous, patented Razor-Cut Wave-Siping design that provided countless sailors sure-footed traction on wet decks. All this gives the shoe the classic Sperry look.

Paul Sperry produced his first Top-Sider boat shoe in the mid-1930s: the Canvas Circular Vamp Oxford. The CVO was a thing of sheer simplicity and utility. The upper was made of a single piece that wrapped the whole foot, lined with cotton for a quick dry. The rubber sole was vulcanized to the upper. Such a simple combination made for stable, comfortable footwear.

An adventurer and innovator, Sperry kept on improving the quality of the Top-Siders. He knew he could still make a more durable leather version of the shoe. So he devised a new tanning method that conditioned leather to be tough enough to sustain prolonged exposure to salt and water without crumbling to bits.

Finally, in 1937, Sperry released the leather Top-Sider, the Authentic Original (AO). It was the first shoe to have the classic moccasin toe stitching and 360-degree saddle lacing. Many sailors found the improvements to be effective. The AO was an instant success.

In the 1960s, subcultures begin to embrace the Sperry sneakers. Surfers liked their casual, laidback looks. Tennis players wore them in the courts. College students saw them as casual, pretty, and fashionable—perfect to pair with chinos, madras shorts, oxford shirts, and loose blazers. Throughout the decades, this preppy style, as it was called, hit the mainstream.

After years of making a living in the seas, the Top-Siders had evolved and successfully stepped on land. The brand continues to do so until now, innovating their designs while paying homage to the signature Sperry style.

Among the brand’s latest releases, the Sperry Sailor style is a hybrid of the classic Sperry boat shoe silhouette and a sneaker’s outsole. Its toe box takes on the elegant almond-toe shape, and instead of rawhide laces, ribbon satin laces fastened the upper, giving the Sperry brand a new, fun look.  

  • The shoe has a full-length Memory Foam footbed for all-day underfoot support.
  • Its upper is made of an easy-wearing “broken-in” leather, which helps the foot feel cool.
Danny McLoughlin
Danny McLoughlin

Danny is a sneakerhead turned sneaker industry expert that believes a good outfit begins from the feet up. His aunt currently isn't speaking to him for wearing a pair of kicks at his cousin's wedding. He spends most of his time trying to keep on top of the latest releases, hitting up his contacts and doing what needs to be done to secure his next pickup. Danny has been featured in prestigious publications such as The Washington Post, The Irish Times, Footwear News and the like.