Canvas Boat Shoes: A Guide For The Over-50S

Boat shoes are a classic wardrobe staple, perfect for the summer months. They are versatile and can be dressed up or down, pairing well with smarter casual clothes such as polo shirts, button-down shirts, short-sleeve henleys, or guayaberas, and tailored shorts or jeans.

When wearing boat shoes, it is best to avoid socks, especially calf-height crew socks, as this can be considered a fashion faux pas. Instead, opt for invisible ankle socks or go sockless, although be aware that this may cause blisters and odour, and can damage the shoes.

When choosing a pair of boat shoes, it is best to select a darker colour such as navy or brown leather, as these are the most versatile and suit the style best. It is also important to ensure a good fit, as boat shoes tend to stretch and get looser with wear.

Boat shoes are a great option for men over 50 who want a casual, yet sharp look for the warmer months.

Wear with jeans, cuffed at the bottom

Cuffed jeans are a great way to show off your boat shoes and complement the nautical look. Cuffing your jeans also helps to emphasise the shoes as the focal point of your outfit. The cuffed jeans and boat shoes combination is a very summery look, so it is best to avoid it in cooler weather.

When wearing boat shoes with cuffed jeans, it is important to avoid visible socks. Boat shoes are designed to show off your ankles, so opt for invisible ankle socks or go without socks altogether. If you do choose to go without socks, be aware that this can cause blisters and odour, and the sweat may damage the leather of your shoes.

When it comes to the jeans themselves, avoid skinny jeans or jeans that are too tapered, as these can look awkward with the wide-set boat shoe. Instead, choose jeans with a slim or regular fit. You should also avoid cuffing your jeans too high, as this can look unbalanced. One or two rolls of the cuff will be enough to show off your boat shoes without looking like you are trying too hard.

Boat shoes typically come in navy, brown leather, or white, and these colours are the most versatile and tend to suit the style best. When choosing a colour for your jeans, opt for a contrasting shade to make your boat shoes stand out. For example, pair light blue jeans with bright red, yellow, or green boat shoes. You can also try to match your upper garment to your shoes by choosing a shade from the same colour family. For instance, you could pair baby blue, stonewashed jeans with red boat shoes and a light red or pink overshirt.

Wear with shorts

Boat shoes are a great option for men over 50, especially in warmer weather. They are a versatile, lightweight, and functional shoe that can be dressed up or down.

When wearing boat shoes with shorts, it is important to consider the style and fit of the shorts. While slim shorts can work, boat shoes tend to benefit from a wider thigh opening. Pleated shorts are also a great option, as they add a bit of shaping and dynamism to the overall look. The length of the shorts is a matter of personal preference, but a good rule of thumb is to choose a pair that ends above the knee.

In terms of colour, navy chino shorts are a classic choice that pairs well with a variety of colours and styles. Beige or tan shorts can also work, but it is important to avoid pairing them with light-coloured boat shoes, as this can create an unflattering combination.

When it comes to styling, a simple white crew-neck t-shirt or a polo shirt can be a great choice to pair with boat shoes and shorts. For a more casual look, a light bomber jacket or a cardigan can be added. It is generally recommended to go for a more relaxed and effortless look when wearing boat shoes with shorts, avoiding overly preppy or try-hard styles.

Lastly, it is worth noting that boat shoes are typically worn without socks. However, if you prefer to wear socks, opt for no-show socks or invisible ankle socks to avoid ruining the look.

Wear with no socks

Boat shoes are a great option for men over 50, offering both comfort and style. They are incredibly versatile, but there are some key things to keep in mind when wearing them without socks. Firstly, it is generally recommended to avoid going completely barefoot in boat shoes, as this can lead to an unpleasant odour and be uncomfortable. Instead, opt for no-show socks, which will help eliminate blisters and irritation while keeping your feet dry and comfortable. These should be in neutral colours, such as white, to match the colour of your boat shoes, but they will remain invisible, maintaining the sockless look.

When wearing boat shoes without visible socks, it is best to pair them with shorter-length trousers or rolled-up hems. This can be a more formal look with cotton trousers or jeans that skim the tops of your shoes, or a more casual look with rolled-up trouser hems. Either way, a little roll goes a long way, so avoid rolling your trousers too aggressively unless you're going for a just-off-the-shore look.

Boat shoes are perfect for the summer and are a great choice when travelling, as they are easy to get on and off and comfortable for long treks. They are also ideal for the beach, as they were originally made for sailors and boaters, or for the office if you work in a business casual environment.

To maintain the classic, preppy look of boat shoes, avoid pairing them with suits or other formal attire. Instead, stick to more casual and laid-back events, and pair them with jeans, colourful chinos, or shorts. Just make sure that the colours balance each other out, with plainer, tailored shorts complementing more detailed, attention-grabbing boat shoes, for example.

Finally, keep your boat shoes well-maintained to ensure they stay fresh and clean. Use a protective spray on leather boat shoes and let them dry for 24 hours after spraying. Keep them out of direct sunlight and avoid getting them drenched to prevent discolouration and changes in texture.

Wear with socks, but make sure they're not visible

When wearing boat shoes, it is generally recommended to avoid wearing socks, or at least to avoid exposing them. Boat shoes are designed to be worn without socks, and exposing your ankles is part of the aesthetic. However, going completely sockless can cause blisters, odour, and damage to the shoes from sweat. Therefore, invisible ankle socks, or "sock-ettes", are a good option.

If you do choose to wear socks with your boat shoes, it is important to ensure they remain hidden. Wearing calf-height crew socks with boat shoes is considered a fashion faux pas. If your socks are visible, it takes away from the casual, laid-back style that boat shoes are meant to convey.

Boat shoes are meant to be worn with a relaxed, preppy look. They pair well with chino pants or jeans, but it is important to cuff your pants to show off the boat shoes' distinctive detailing. A simple single or double cuff will do; there is no need to go overboard and cuff your jeans so high that they resemble capri pants.

In terms of colour, it is best to choose dark socks that contrast with the colour of your pants. Dark socks, such as navy or brown, will generally go better with your boat shoes than light-coloured socks.

Wear with a casual shirt and blazer

When wearing boat shoes with a casual shirt and blazer, it's important to strike a balance between smart and casual. Here are some tips to achieve a stylish and polished look:

• Opt for a casual shirt in a solid colour or subtle pattern such as gingham, plaid, or stripes. A button-down shirt or a polo shirt can work well with this ensemble.
• Choose a blazer in a complementary colour to your shirt. A navy blazer is a versatile choice and can be paired with a variety of shirt colours. Alternatively, you could go for a more casual, unstructured blazer in a lighter colour such as beige or light grey.
• Ensure your blazer is well-fitted to create a polished silhouette. A tailored blazer will help to elevate the overall look.
• When it comes to the boat shoes, opt for a darker brown or navy colour as these are the most versatile and classic choices. Leather boat shoes will also add a touch of sophistication to your outfit.
• As boat shoes are typically associated with a more casual style, it's important to balance the formality of the blazer. Consider rolling up the sleeves of your blazer or leaving the bottom button unfastened to create a more relaxed vibe.
• To complete the look, choose a pair of trousers that complement your blazer and shoes. Chinos or khakis in a neutral colour such as tan or beige are a good choice. Ensure the trousers are well-fitted and cuffed to show off the boat shoes. Avoid skinny trousers or bootcut jeans as these can clash with the style of the shoes.
• When it comes to socks, it's best to go for invisible ankle socks or no-show socks. Visible socks can detract from the elegance of the outfit, so it's best to keep them discreet.
• Finally, pay attention to the small details such as your choice of watch or accessories. Avoid anything too flashy or formal, as this may clash with the casual nature of the boat shoes. Opt for more understated pieces that enhance the overall ensemble.

Frequently asked questions