Mens Summer Style: Boat Shoes

Boat shoes are a men’s summer style classic and dare we say it, essential. From the shores of Sicily to the college campuses of California, to the backstreets of Bondi – everyone’s got a pair. But boat shoes are also a statement. They convey a certain air of privilege and preppy style that no other shoe can match. While this might not be an image every man cares to convey, you can’t deny their absolute versatility, and ability to be dressed up or dressed down, making the Boat shoe a key part of men’s summer style.

The History of the Boat Shoe

The moccasin/loafer-styled fashion staple didn’t start its commercial life on the feet of affluent holiday-goers. It was 1935 when Paul Sperry noticed his pup’s ability to not slip while running on ice. This budding curiosity birthed an international sensation. Sperry took a small knife and began to cut grooves into the bottom of his shoes and to his satisfaction, he had more traction when walking on slippery surfaces – such as the surface of a boat deck.

Early Sperry advertisements emphasised safety and versatility.

Soon after, retailers Abercrombie & Fitch began distributing the shoe. Utilising the product’s non-slip application, the U.S. Navy negotiated the right to manufacture Sperry’s shoes for its sailors. As a result, Sperry became synonymous with boating footwear and the brand became a household name.

The Sperry Legacy

What is particularly interesting is the boat shoe’s translation to the affluent. It’s an odd train of thought, but one worth indulging.

In its early days, the Sperry shoe usually meant wearers had a practical use for the shoe. That practical use is in the traversing of boats owned for purely pleasure-based pursuits. Therefore, a pair of Sperry’s meant money.

It wasn’t long before people began taking to this idea, and sailors and non-sailors alike were donning the shoe. Nowhere was this more evident than in the image-obsessed dorms of colleges across America.

The Boat Shoe Today

Sperry now shares a competitive market with larger companies like Timberland and more niche businesses such as Rancourt & Co. and Quoddy. Nevertheless, the tradition of the original is alive in all boat shoes.

Two main trends are inclusive when wearing boat shoes:

  • Rolling up the cuffs of trousers.
  • Not wearing socks.

These customisations are a throwback to the origin of the shoe – you don’t want your cuffs or socks getting wet when sailing through the Pacific Islands. Boating or not boating, these rules should be observed at every opportunity.

After finding that the original shoe’s black sole was staining the deck of his customer’s boats, Paul Sperry decided to use white instead.

The Men’s Gold Cup 2-Eye is the most traditional and safe form of the boat shoe.

Minus the gold cup, this is a warmer answer to the original navy/white combination.

Finally, the all-white Nautical Boat Shoe pays homage to the brand’s nautical roots with accents of blue, red, and white.

Quoddy made-to-order styles are about as good as boat shoes can get. The Blucher offers a different spin on the above and includes a 3-eye lace style and a leather cover. The degree of customisation and lasting quality are worth the price increase.


Though versatile, the boat shoe is the core of a broader summertime uniform. Specific pants, shirts, and accessories are essential to completing the look.


You have two strong contenders in this domain: The Polo or the floral.

Much like Sperry, Polo’s branding is synonymous with the relaxed, affluent lifestyle that democratic capitalism has afforded us. Though there are many to choose from, the original navy-blue Polo is difficult to overlook and matches well with the original navy/white Sperry’s.







MORE: ‘Excellence Embodied: 50 Years of Ralph Lauren’

The second contender is the floral: a timeless summer favourite and a more relaxed approach to the overall look. Like the boat shoe, the floral will continue to be dominant across many 2018 summer styles. Luckily for you, we recently published a comprehensive piece on this type of shirt. Gianetto Portofino’s Blue Flower Field is a not-too-casual winner in this instance.


The boat shoe versatility extends beyond the foot and up the leg. Will you wear slacks or shorts? Here are two good options.

Mens Summer Style ChinoBeginning once again with intended tradition, we have the stone, khaki or tan coloured chinos; popular in the mid-1950’s and popular now. A quick roll of the cuff will provide a more casual appearance, as will a bolder colour like a red or dark green. Ralph Lauren is a go-to in the chino department, as are Paul & Shark. For something a tad more affordable, both MJ Bale and Country Road offer a good selection.

Most of the Australian summertime fashion calls for shorts. Venroy’s linen offering has become an Australian men’s summer style must have, however, they do lack formality. Whatever you choose make sure they site well above the knee.


Kangaroo Leather BeltDepending on your level of casual-ness, your shirt may or may not be tucked. In both cases, a trusty brown belt is the obvious option here and will match well with most boat shoes, regardless of colour. Woven belts tend to be an icon of men’s summer style. Step your weave up a notch with a belt from Kangaroo Belt Co.


A Panama hat doesn’t just serve a practical purpose, they also elevate your aesthetic significantly. Check out our coverage of the Panama Hat Co, located in Sydney.


Continuing with light-brown accents and white tones to compliment your look, let’s finish off with a casual dress watch. The MeisterSinger No 01 won’t take too much attention away from your shoes, but still makes a humble statement.

RELATED: ‘Top 10 Watch Brands For First Time Buyers’


Paul Sperry combined true practicality in pleasure in creating his coveted boat shoes. Alongside several other men’s summer style staples, the boat shoe will be the shoe of choice for many summers to come.


Jay is a writer and content producer for The Versatile Gent.

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