Do you wear boat shoes with socks? | Timberland (2024)

For years now, boat shoes have been as popular on the high street as on the high seas. They’re something of a summertime staple, giving a relaxed, preppy look to your smart casual outfit, fitting in everywhere from weddings to festivals. But as popular as they are, boat shoes have a way of confounding the average wearer. Just how casual are they? Should you go sockless or proudly socked? Here are all your boat shoe queries answered.

Do you wear socks with boat shoes?

Boat shoes are designed to be comfy and airy without socks, and most people keep their ankles bare for the classic maritime look – preferably with no-show socks. If you’re going for an 80s preppy look, however, socks and boat shoes are definitely part of the uniform.

If you’re worried about the sockless look with leather, try something even more casual, like a pair of light canvas boat shoes. They have an unmistakably laid-back vibe going on, and you’ll be much less self-conscious.

Of course, if you feel totally weird wearing shoes without socks, or just want an extra layer for hygiene purposes, you can always slip on a pair of no show socks or liner socks. Just make sure you roughly match the colour of the outer or lining of the shoe, as they may still be visible from certain angles.

As we’ve mentioned above, there are a few looks that combine boat shoes with socks. The 1980s vibe that’s happening is one example – the socks are prominent against the ankle-length straight pants, and proudly so. A laid-back academic look, with a loose fitting jacket and pants also works with boat shoes and wooly socks. In both cases, just make sure they’re your good socks – an old, well worn pair really won’t cut it.

Should you wear boat shoes with jeans?

Boat shoes and jeans go perfectly together. If you’re aiming towards a nautical look, get shorter jeans or roll up the bottoms to expose the ankles and lower shins. Skinny jeans can work too, giving a smart silhouette that accentuates the shoes.

If there’s one rule about boat shoes with jeans, it’s probably to avoid shiny leather, as it can look a little jarring. With blue jeans, a pair of matt brown boat shoes will always work, but against light jeans, try a pair of blues (unless the jeans are light blue). If you’re in black or dark indigo jeans, you’re best off going for darker boat shoes in black or navy.

Are boat shoes cool?

If you mean cool in the temperature sense, the answer’s yes, especially when worn without socks. If by cool you mean ‘fashionable,’ it’s still a big yes! Boat shoes are a timeless classic that should be in every summertime shoe rack.

Their low sides and flexibility to be worn without socks mean boat shoes are perfect for the summer. The air is free to move around your feet, giving a natural ventilation that’s just what you need when it’s warm. And with every step you take, you’re circulating the air even more.

The look itself is evocative of the good life, thanks to the shoes’ association with sailing, harbourside lifestyles and days spent chilling in the cool coastal breezes. It’s a look anyone can pull off, whether you’re going for a preppy college look or walking that subtle line between formal wear and classy weekend leisure. Pull on a pair of chinos and a polo shirt, throw on a blazer, and that’s it – the look’s complete.

A sea air without the sea legs

You might already be the type of person who’s cool without really trying, but boat shoes just prove your point: you’re ready for summer but you’re not going to let your style standards slip as you dress down. Boat shoes deliver the look on a plate. Just remember to leave your socks at port unless you’re going for a very specific look; and even then, choose the socks well – any old pair won’t do.