Deck shoes: the acceptable face of practical footwear. They were designed to stop sailors stacking it on wet decks, but somewhere along the way they became a summer staple for the types men who enjoy a well-made Negroni and understand the value of a well-cut suit.
Unlike most technical footwear, they don’t scream about their functionality. They just work. Equally at home with a linen suit as they are with swim shorts and a half-buttoned shirt. And it's not just the summer months they're useful for either. The current proliferation of chunky, commando-sole styles means they'll gladly carry you through the winter months too.
Granted, they’ve had their ups and downs – embraced by the prep movement, hijacked by unruly frat boys – but when done right, they’re one of the easiest shoes to wear. And thanks to the rise of chunky-sole deck shoes, they’re nop longer limited to the confines of the summer months. Here’s how to make them work, followed by the best brands making them in 2025.
What are deck shoes?
Deck shoes have been knocking about since the 1930s, when a bloke called Paul Sperry cut grooves into the soles of his shoes so he wouldn’t go flying overboard. The result: a shoe that offered serious grip on wet decks, with a flexible leather upper that moulded to the foot.
Fast forward a few decades, and they’ve been absorbed into the menswear lexicon – first by Ivy League types, then by Italians, and now by anyone who understands that a good summer shoe needs to be lightweight, comfortable, and easy to wear.
The DNA remains the same – soft leather or canvas uppers, stitched moccasin-style construction, laces threaded around the collar – but the styling has shifted. Modern deck shoes aren’t stiff or overly polished; they’re relaxed, easygoing, and, crucially, should look like you’ve owned them for a while. A classic pair of smart-casual shoes.
How to wear deck shoes
A good deck shoe is a cheat code for summer dressing. It works with almost anything – tailored shorts, pleated trousers, lightweight denim – and sits in that sweet spot between casual and refined.
The best approach? Keep it loose. A relaxed linen shirt and chinos will always work. A slightly oversized blazer and wide-leg trousers? Even better. If you want to wear them with denim, go for something cropped or cuffed – the goal is to keep the silhouette airy, not stuffy.
Most importantly, no socks – or at least no visible ones. If you’re tempted to pair them with ankle socks, go barefoot instead. It’s not worth the risk.
The rise of chunky deck shoes
The past few years have seen a shift towards more substantial footwear. Soles have got bigger, silhouettes have got chunkier, and deck shoes – traditionally a lightweight, low-profile shoe – have followed suit.
It makes sense. A classic deck shoe is great for summer, but as soon as the temperature drops, they start to feel a bit flimsy. By adding a chunkier sole – usually a commando tread for extra grip – brands have taken the deck shoe beyond its seasonal limitations. Now, it’s less about Riviera holidaywear and more about everyday utility.
A style like the Timberland 3-Eye Lug is the perfect example. It takes the familiar shape of a deck shoe but gives it a workwear edge, making it feel more substantial. Paired with selvedge denim or wide-leg wool trousers, it adds structure to an outfit without looking too formal. If you like the idea of deck shoes but want something with a bit more presence, this is the way to go.
The best deck shoe brands right now
KLEMAN
A French take on the deck shoe, which means a little more ruggedness and a little less prep. KLEMAN’s versions are built for durability – chunky soles, vegetable-tanned leather, and an overall feel that’s more workwear than waterfront. If you like your shoes to look like they’ve been places, these are the ones to go for.
Velasca
Velasca operates in that sweet spot between classic and contemporary. Its deck shoes come in full-grain leather and supple suede, with a slightly vintage feel that makes them an easy alternative to loafers. If you like the idea of a deck shoe but want something that leans more Riviera than Rhode Island, this is a solid option.
Oliver Cabell
This brand takes a modern approach to deck shoes, blending traditional craftsmanship with contemporary styling. The result? A hybrid between a loafer and a slip-on, made from Italian suede and finished with a cushioned footbed for all-day wearability. Think of these as deck shoes for people who like the idea of them but don’t want to look too nautical.
John Lobb
If you want to take the deck shoe into full-blown luxury territory, John Lobb is the brand to know. Think fine-grain leather, hand-stitched detailing, and the kind of craftsmanship that justifies the price tag. They’re a little too refined for anything resembling actual boating, but if your summer plans involve long lunches rather than setting sail, they’re a strong choice.
Sperry
The original. Paul Sperry’s eponymous brand more or less invented the deck shoe, and it’s still one of the best places to find the classic, no-frills version. This is the quintessential East Coast prep shoe – slim, lightweight, and built for effortless summer dressing. It’s the kind of thing that works best with a relaxed oxford shirt, tailored shorts, and a sense of insouciance.
Sebago
Sebago is another brand with serious deck shoe credentials, but it leans more European in its execution. The construction is still traditionally American – hand-stitched leather, siped soles – but the designs have a slightly sleeker edge, which makes them an easy choice if you like your deck shoes to feel a little more considered.
Timberland
Most people associate Timberland with its chunky, wheat-coloured work boots, but the 3-Eye Lug deck shoe is arguably just as iconic. Taking the classic deck shoe silhouette and slapping a big, commando-style sole underneath, it’s bulkier, grippier, and built for more than just leisurely walks along the pier. Wear them with raw denim and a boxy chore jacket for a look that feels more workwear than waterfront.
Yuketen
If you’re into American heritage footwear, you’ll already know Yuketen. The brand makes some of the best hand-stitched moccasins around, and its deck shoes are no exception. Made in small batches from thick, full-grain leather, they’re built to last and only get better with age. These aren’t deck shoes for sipping rosé on a yacht – they’re for people who like their shoes to look and feel substantial.
Next up: The complete guide to smart casual shoes.
