5 Boat Shoes for the Tail End of Summer


The afternoon shadows are beginning to get a little long in the tooth, so to speak. The tail end of summer is upon us, but that by no means suggests it is time to trade in your boat shoes for your dessert chukkas. In fact, the late summer is one of the best times to rock these shoes – and these are our top five favorites for the end of the Summer (and start to the Fall).

Jack Erwin


This brand is still new to us, but we have been nothing but impressed with their presentation, service, and craftsmanship. This Jack Erwin boat shoe is stitched out of 100% leather, with extra tough outsoles and extra cushy microfoam insole. It is ‘urbanized’ more than the traditional boat shoe, which means it is prepared for the ravages of the typical urban landscape, including hot tarmac, gum, and city rash. These also feature an extra touch of class, so you can wear them to the office just as easily as out to the pub.

Get them here.

Sperry Billfish


Sperry is a staple for boat shoe aficionados and these Billfish 3-Eyes are the real deal. These feature their classic leather top, slip-resistant rubber sole, extra cushioned footbed, and a two-tone appearance package that gives these a touch of finesse, similar to the racing stripes on a Shelby GT-350. A lot of Sperry’s are a little dated for some guys taste, but these find a happy medium by combining the classic style with some notable modern style upgrades.

Get them here.

Rockport Ports


It it a boat shoe, casual shoe, or a dress shoe? Yeah, exactly, we think that almost anything goes with these leather Rockport Ports which feature a classic “nautical flair” which will still be stylish for decades to come. We’ll let you in on a secret, these have been around longer than the first Xbox console, and they only seem to become classier the older they get. These are a bit chunkier and cut higher than the typical classic style, but if you like to rock your boat shoes with socks (and some of us do), these will give you that option without looking out of place.

Get them here.

Reef Deckhand Low


Do you prefer your shoes built for speed or comfort? Well, unlike some other topics we won’t mention, these Reef Deckhand Low’s are built for both speed and comfort. They accomplish this by mating the flexible canvas and supportive cushioning of a sneaker with the comfort and profile of a classic boat shoe. While these may be a bit more on the casual side, we have no doubt that these could be dressed up a with a slim fitting suit or all the way down with just a pair of swim trunks and a beer.

Get them here.

And don’t be afraid to stretch most of these out for a good portion of the Fall season, as these are not your grandpa’s summer boat shoes. These are sleek, sporty and modern and therefore they don’t have to play by the same rules as most other boat shoes.


About Pamela Causfield

I'm a digital nomad and story teller that writes for Urbasm and a few other websites on men's interests, style, relationships and whatever tickles my fancy. In my spare time I like to play the field in search of my prince, travel, and consider myself an artisan of sarcasm at times.