Remember those Ralph Lauren boat shoes I wrote about a while back? They are cool and all, but as I said back then, fashion denim doesn’t exactly cut it if you need footwear sturdy enough for, you know, an actual boat.

The two most well-known examples of legitimate boat shoes are Sperry Top-siders and Sebago Docksides. Need help deciding which is best for you? Read our comparison here!

UPDATE (05/17/16): Just got some cool new Cooper boat shoes from Jack Erwin! Read the review here!

Sperry Top-siders are the “original” boat shoe (according to Wikipedia), created in 1935 with heavy-duty leather uppers and grooved rubber outsoles to stand up in the harsh, wet conditions of country club cigar rooms across the country. Thank goodness they go great with trousers and herringbone jackets!

No really, they were first originally meant to provide durability and traction on the slippery decks of sailboats. Somewhere along the way, though, they caught on as an upscale casual form of footwear for the elite. Rich people are crazy.

Sebago came on the scene just over 10 years later (Wikipedia), also eventually gaining popularity for their fashionability rather than their functionality.

What is the appeal of these strange shoes? Perhaps it is their rugged-yet-refined sense of fashion – tough and outdoorsy, yet not childish like sneakers. They can (and should) be beaten up – and many think they look better that way.

They also offer simplicity, comfort, and convenience – you can slip them on easily, with or without socks (preferably without), and they pair well with casual trousers, jeans, and even SHORTS! WHAT?!

Comfort

I find the Sperry Top-siders heavier, stiffer, and more cushioned, while the Sebago Docksides are more flexible and closer to the ground. This translates to the Docksides being lightweight and loose-fitting, but also having a harder “step” than the Top-siders, which can cause tired feet after a long day of heavy walking. For casually beating around town, though, the less restrictive feel of the Docksides can’t be beat. Verdict: DRAW!

Fit

I am usually a 10.5 US in sneakers and a 9 or 9.5 in dress shoes. Both brands in 9.5 fit me perfectly!

Construction

Both brands’ uppers as well as interior linings are made from heavy-duty leather, with metal eyelets for the rawhide laces. Outsoles are rubber (in contrast with “manmade” soles which are made from cheap crappy plastic). Verdict: DRAW!

Appearance

The Sebago Docksides look EXACTLY like the Sperry Top-sider A/O shoes. The Top-siders pictured here are the Cup boat shoes, which are shaped a little differently (slightly rounder toe), have a textile insole (instead of leather), and a more sneaker-like outsole. Sperry makes other boat shoes in just about any style and color combination you can imagine. I got a pair of Bluefish Top-siders for Yoselin that amalgamates black suede, patent leather, zebra print, and royal blue lacing. They are awesome.

Both brands’ versions of the classic boat shoe look virtually identical, but Sperry wins for the sheer expansiveness of the rest of their lineup. Verdict: SPERRY!

Cool Factor

There is a good chance you aren’t buying these shoes to use on a yacht. You probably will be wearing these to school or work or a party over the weekend. If you want to go with the original, the Sperry Top-sider A/O is the most recognizable and iconic of all boat shoes. If you don’t care about recognition all that much, the Sebago Docksides are an equally great shoe with just about the same pedigree. Verdict: SPERRY (if you like impressing people with brand names) or SEBAGO (if you like being a little different).

Final Verdict

For unusual colors and designs, go with the Sperry Top-siders. However, if you are going for the classic look, both shoes are pretty much carbon copies of one another; lean toward Sperry if you are a slave to trend, or toward Sebago if you are one of those counter-cultural types. (Sebago’s shoes also tend to be a little less expensive.) And guess what, both companies are owned by Wolverine, so they’re taking your money either way! Hooray!

The truth is, boat shoes float in and out of youthful fashion. On the other hand, they are fairly consistent as a staple in the shoe closet of the quintessential Old Guy Who Kind Of Dresses Up For Work. In any case, having a pair handy all the time will allow you to benefit from its convenience and versatility, and then whenever boat shoes periodically hit the fad train, so much the better for you!

The Sperry Top-siders pictured in this article can be purchased here. You can see their endless selection of other models here.

The Sebago Docksides are here. Although not quite as comprehensive as Sperry’s, their selection is still pretty wide; view them here.

Which of the two brands is your favorite? Let us know in the comments!

UPDATE (05/17/16): Just got some cool new Cooper boat shoes from Jack Erwin! To see how they hold up against these, read the review here!