Boat Shoes Style Guide

Boat shoes have rubber soles with grooves to ensure they are slip-proof and have either leather or canvas upper. The sailor Paul Sperry came up with the idea for the deck shoe in 1935 when he noticed that his dog didn’t slip when walking on ice. This inspired Sperry to carve the bottom of a shoe to gain the same stability when sailing. Around the 1970s, boat shoes became popular on land as well, and nowadays, they’re a part of both casual and smart attire. 

Unlike trainers, men’s boat shoes are stylish enough to wear to the office, thanks to their leather build. But at the same time, they are informal enough to pair with shorts while on holiday. They are the true definition of versatile. And unlike popular belief, you don’t have to store them away when the weather gets chilly. This article will give you our top suggestions for stylish boat shoe outfits.


Do I wear socks with boat shoes?

Before we jump into the style guide, we have to talk about the most burning question when it comes to boat shoes - socks or no socks? 

The classic way to wear this footwear is without socks. Since canvas and leather boat shoes are usually for summer, this makes them extra breezy. Also, a sock draws attention away from the fine details of the shoes.

You can always wear no-show socks for extra comfort, as long as the ankle stays bare. But this rule is not set in stone. For a more preppy, 1980s look, you can wear graphic print socks with the boat shoes. But this might be a bit of a bolder statement and harder to pull off.


Summer outfit: Chino shorts and a white tee

When Sperry invented the boat shoes, he had a casual look in mind, one that would match well with a day out on a boat. The chino shorts, with their nautical esthetic, capture that effortless style.

You can pair tan canvas boat shoes with almost any colour of chino shorts. However, we recommend that you don’t go too bright. Khaki or light green will go well, along with a basic white T-shirt to keep it clean. You can throw a denim jacket on top for the evening.


Springtime preppy: Chino shorts and a sweater

The chino shorts can still be a part of your attire during the not-yet-hot spring evening. Wear navy blue shorts with an Oxford shirt and a light grey sweater to keep you warm yet dapper. This could be a good grey boat shoes outfit since the colour is quite casual.

Business casual: Slim-fit trousers and a blazer

Shorts are unsuitable for the office, but boat shoes can still make an appearance. This is as long as you style them to look professional. For a navy blue boat shoes outfit, choose a pair of khaki, beige, or orange (if you’re feeling bold) slim-fit chinos. Make sure you cuff them at the bottom to reveal your ankles.

At the top, you can wear a white T-shirt with a dark blue blazer. For a more formal office, replace the tee with a light blue button-down and add a dark brown leather belt.


Date night: Jeans and a leather jacket

The combination of casual and smart makes this footwear a great choice for a chill night on the town. So it’s no wonder one of the most popular men’s outfits with boat shoes includes jeans.

Wear your tan or brown Timberland boat shoes with slim-fit dark jeans. Once again, don’t forget to cuff the bottom to expose your ankles. Combine that with a casual white button-down shirt and a tan leather jacket to match the shoes and edge up the ensemble.


Cold weather look: bare ankles with a warm sweater

It depends on how cold your locale gets, but boat shoes can also sustain lower temperatures. The leather boat shoes are slip-proof, water-resistant, and can handle some rain. With that in mind, we offer another navy blue boat shoe outfit. Pair the shoes with cropped red chinos to contrast the colour.

At the top, layer a graphic design black and white sweater on top of an Oxford shirt. You can finish it off with a dark grey wool coat. If your ankles can’t handle the cold, you can wear graphic socks that match your sweater.


Women’s boat shoes outfits

Both women and men can enjoy wearing boat shoes. There is no gender restriction. However, with women’s boat shoes, there tends to be a wider variation in colours and styles. As for the outfits, the options are endless, but here are a few of our suggestions:

  • For a light grey boat shoes outfit, pair the shoes with a checkered midi sundress and a cream tote bag. This outfit is great for a beach day or brunch with friends.

  • Wear your navy boat shoes with light-wash mom jeans rolled up. Finish it with a white, oversized t-shirt (tucked in) with a fun, bold print for a casual look for errands. 

  • Wear dark brown boat shoes with white, cropped, wide-legged jeans. At the top, wear a cropped brown sweater. This is a smart outfit that could look good on a night out.

  • Pair your grey boat shoes with grey leggings, an oversized pastel hoodie and a cap for complete comfort.


Complete your wardrobe with a pair of boat shoes

We hope this article inspired you to experiment more with your boat shoes, whether in spring, summer, or autumn. And if you don’t already own a pair of this versatile footwear, why not browse the Timberland boat shoes for men and women? Find shoes that you can use every day, whether out and about with friends or working hard at the office.

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