ICONIC, preppy and more than a little bit nautical: if you're looking for a classic bit of maritime footwear, the boat shoe has it all.
Sailing down the Med may seem unlikely at the moment, but that's not to say you can't bring some suave Riviera style to your wardrobe this winter. Boat shoes work just as well with jeans and an overcoat as they do with a chino short and a crisp Oxford shirt—plus they're undeniably comfortable and easy to dress up or down.
Originally dreamt up by one Paul Sperry in Connecticut after he noticed the non-slip grooves in his dog's paws, his boat shoes were first introduced in 1935—giving sailors some much-needed foot traction on slippery decks.
Four years later, Sperry was manufacturing his 'Top Siders' for the U.S. Navy, but it wasn't until the 80s that they really took off as a full-on trend, thanks to a mention in Lisa Birnbach's influential 'The Preppy Handbook.'
They may not have had the 'coolest' of reps since then (no offence, dads) but fashion, as we know, is nothing but a fickle beast, and these bad boys have come round full circle again—appearing on runways from the likes of Miuccia Prada and officially reaching cool Instagram status.
Below, we've rounded up the best versions that are fresh off the boat and available to shop now.
This article and featured products have been independently chosen by Sun journalists. It contains links which are ads, and if you click a link and buy a product we will earn revenue.
1. Best brown leather boat shoes: Timberland Men's Classic 2 Eye Boat Shoes
Timberland's Classic 2 Eye Boat Shoes are available in a range of 11 colours and styles, but we have to say we're loving the timeless rugged appeal of 'Brown Sahara'.
With a leather outer, gum rubber sole and lace detailing, it's a strong choice for anyone looking for a boat shoe—and reviewers are impressed with the quality too, commenting on the 'durable, soft leather' and 'bang on' design.
- Shop all boat shoes at Amazon here
2. Best boat shoes for style cred: Kickers' Lennon Boat Shoe
- Kickers Lennon Boat Shoe, £56 (was £80) from Kickers - buy here
Kickers has brought back a classic here, with an all-new Lennon boat shoe reimagined from the archives.
Crafted from leather and with chunky rubber soles, these are ideal for wintry walks, while the cushioned ankles provide maximum comfort.
Featuring the iconic red and green Kickers tabs to finish, these look set to trend: we've already spotted photographer, stylist and model Michael Sabuni rocking a pair on his Instagram.
3. Best for heritage style: Barbour's Stern Leather Boat Shoes
- Barbour Stern leather boat shoes, £100 from Selfridges - buy here
If you're going to do a classic shoe, you can rely on a heritage brand to deliver—and Barbour hasn't disappointed with this chunky iteration of the traditional boat shoe silhouette.
Crafted from smooth leather and trimmed with signature lacing, you'll find embossed branding at the side and a rich navy colourway that makes a great alternative to black or brown.
Treat these well and they'll last the distance.
4. Best for casual wear: Next's Navy Canvas Stag Boat Shoes
- Navy Canvas Stag Boat Shoes, £30 from Next - buy here
If laidback and casual is more your style, a non-leather boat shoe lends a more dressed-down look—while still being slightly more formal than trainers.
If that sounds good to you, then Next's canvas boat shoes are a solid choice. They still have all the boat shoe trimmings including that classic lace-detailing contrast soles, with a blue canvas upper that was made for sunny park days.
5. Best designer pair: Christian Louboutin's Paqueboat Suede Deck Shoes
- Paqueboat suede deck shoes by Christian Louboutin, £625 from Matches Fashion - buy here
If you're looking for easy-wearing, it doesn't get much more effortless than a slip-on pair of boat shoes.
We've turned to shoe design stalwarts, Christian Louboutin, who've pulled out all the stops with the Paqueboat boat shoe.
Described as a hybrid between moccasins and trainers, these are crafted from soft brown suede, with stitch detailing and a chunky sole that makes them perfectly relaxed.
Finished with the inimitable logo-embossed red sole—if you've got cash to splash, these are definitely for you.
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