Back in 2020, after a long stretch of sneaker dominance that saw the global reselling market swell to a value of over £6 billion, people began to ask if things had maybe... gone a little too far. For many, a malaise was spreading across their once-revered shoe rack. Menswear commentators speculated that we were living through the dying days of the trainer, and since then the existential concept of a "post-sneaker world" has been hotly debated on hype sites and podcasts, in newspapers and pubs. Of course they would always have a place, but it was clearly time to experiment with casual alternatives.
For a while, loafers emerged as the obvious winner; they surged in popularity and dovetailed with the prep resurgence and return of classic menswear. But check out the summer lookbooks and collaborations currently being rolled out by brands, and another worthy challenger emerges: the boat shoe.
Needless to say, the boat shoe never actually went away, and three American shoemakers are perhaps most synonymous with the style: Sebago, Sperry, and Timberland. The New England-based brands all have extensive histories, but Sperry was the first to produce a boat shoe all the way back in the 1930s, before Sebago launched the Dockside in the 1970s and Timberland arrived with their version not long after that.
Any talk of the boat shoe's latest moment in the sun should be tempered by their cross-generational appeal and the regularity of their apparent comebacks. The reasons for the boat shoe's long-lasting success are simple: they're really comfortable and they're really versatile. They also answer an important question posed by the post-sneaker world, in that they look good with shorts (they were designed for being on a boat, after all).
Despite all the positive aspects of the silhouette, it has also been guilty by association of being too fratty, too old and too boring. In the UK, they're still a bit Boat Race, a bit weekend at the Henley Regatta. But maybe that's not a problem in 2023. The revived interest in prep and Ivy League dressing - albeit in an updated way - and TikTok's obsession with the "old money aesthetic" (6.2 billion views and counting) mean that those old qualms don't matter as much anymore.
Prep's return, in particular, has been laying the groundwork for boat shoe season. Going back to the 1980s - when the Sebago Dockside appeared in The Preppy Handbook - boat shoes have been a prep staple, and their origins as footwear for boat-owning New Englanders always gave them an Ivy League persuasion. The shoe is perfectly positioned to profit from the prep comeback that began five years ago and shows no sign of slowing down.
More recently, all the aforementioned brands have lent on their prep connections to push the style even further. Sebago announced a collaboration with Drake's few weeks ago, Sperry has worked with New York brands Noah and Rowing Blazers, and the Timberland 3-Eye Lug was reworked by Aimé Leon Dore in 2021 and 2023.
But it's not just prep-adjacent brands that are taking part in the boat shoe's relaunch. A-COLD-WALL* also worked on a Timberland 3-Eye Lug, with designer Samuel Ross focusing on hardwearing materials like ballistic nylon for his interpretation of the silhouette, while Supreme previously constructed the same shoe from woven leather. Palace, meanwhile, dressed Sperry's OG Top-Sider in a branded denim for Summer 2022.
The boat shoe is a five-decade staple for a reason, and new interpretations are showing that the silhouette isn't wedded to its Ivy League heritage. Isn't that reason enough to climb aboard?