Styling Sperry Boat Shoes: A Guide To Looking Sharp Afloat

Sperry boat shoes have become a staple in every wardrobe since Paul Sperry created the boat shoe in 1935. The shoe's evolution from a practical shoe for sailors and boaters to a style icon for any occasion is a testament to its iconic status. With its quality materials, hand-sewn design, and slick shape, Sperry boat shoes offer both functionality and aesthetics. Whether you're attending spring races, casual get-togethers, weddings, or just spending the afternoon at the pub, here's a guide on how to style your Sperry boat shoes to elevate your look.

Wear with jeans

Boat shoes are a versatile footwear option that can be dressed up or down, depending on the occasion. When it comes to styling them with jeans, here are some tips to consider:

Choose the Right Jeans

Select a pair of well-fitted, tapered or straight-leg jeans in a darker wash. Avoid wide-leg styles as they can look disproportionate with the small moccasin toes of boat shoes. Dark denim, such as a dark blue or black wash, will help elevate the overall look and make it more polished. Cuffing the hems of your jeans can also complement the shoes and draw attention to them.

Consider the Occasion

Boat shoes are casual footwear, so they pair well with a casual outfit. For a smart-casual look, opt for a polo shirt, button-down shirt, or a short-sleeve henley. You can also layer with a blazer, but remember to keep the rest of the outfit more casual to balance the look. Boat shoes are not suitable for formal events or occasions that require a tie.

Play with Colours and Textures

When wearing boat shoes with jeans, consider the colour and style of your outfit. For a classic and versatile look, choose a darker brown pair of boat shoes as they will go with almost everything. Navy is another good option, but it doesn't pair well with denim. Avoid wearing light-coloured boat shoes with light-coloured jeans, as the contrast will be minimal, resulting in a less stylish ensemble.

Know Your Socks

Traditionally, boat shoes are worn without socks. If you prefer to wear socks, opt for no-show socks that won't be visible. Visible socks can detract from the overall aesthetic of the boat shoe and are generally considered a fashion faux pas.

Break Them In

Boat shoes may take some time to break in, so start by wearing them for short periods and gradually increase the duration. They will eventually conform to your feet and become more comfortable.

Location and Weather

Boat shoes are typically considered a spring and summer footwear option and are best worn in warmer weather. They are perfect for coastal towns, beach trips, and locations with a casual dress code.

In summary, when styling boat shoes with jeans, opt for a well-fitted pair of dark-wash jeans, and pair them with a casual or smart-casual outfit. Choose a darker colour for your boat shoes, and avoid visible socks. Boat shoes are a versatile and comfortable option for many occasions, adding a touch of nautical elegance to your wardrobe.

Wear with colourful chinos

Sperry boat shoes are a versatile option for any wardrobe, and they can be dressed up or down depending on the occasion. If you're looking to style your boat shoes with colourful chinos, here are some tips to help you create a stylish and well-balanced outfit:

Firstly, it is important to consider the colour combination. The key to pulling off this look is to ensure that your chinos and boat shoes are contrasting colours. For example, if you choose bold-coloured chinos such as red or green, it is advisable to opt for a more neutral-coloured shoe, like brown. This will create a harmonious look that is not too overwhelming.

When it comes to the fit of your chinos, it is recommended to go for a more tailored style. Avoid wide-leg trousers as they can look out of proportion with the small boat shoe silhouette. Instead, opt for a pair of chinos with a tapered or straight-leg cut that complements the shape of the shoe.

The length of your chinos is also important. Ideally, the hem should fall just above the ankle, skimming the tops of your shoes. This will showcase the unique details of your boat shoes, such as the laces and rubber soles. If your chinos are too long, consider rolling them up a little, but avoid rolling them too high, as this can detract from the overall aesthetic.

In terms of styling, you can experiment with different ways to tie your shoelaces. The traditional rawhide laces can come undone easily, so consider trying a different knot, such as the barrel knot, which will give your shoes a more preppy look. You can also play with texture and pattern by pairing your colourful chinos with a knit polo shirt or a camp collar shirt.

Lastly, while boat shoes are typically worn without socks, you can opt for no-show socks if you prefer. This can provide added comfort and help prevent odour, especially during the warmer months when your feet tend to sweat more.

By following these tips, you can confidently style your Sperry boat shoes with colourful chinos, creating a polished and well-put-together outfit.

Wear with shorts

Boat shoes and shorts are a perfect combination for summertime. Here are some tips on how to style Sperry boat shoes with shorts:

For a casual, laid-back look, pair your boat shoes with a simple pair of shorts. This will let your boat shoes stand out. Avoid wearing socks with this combination, as it can ruin the look. However, no-show socks can be worn for added comfort. For a more detailed, attention-grabbing boat shoe, opt for a plainer pair of shorts to maintain a balanced look.

For men, Sperry's Authentic Original Boat Shoe in a neutral colour such as khaki, washed blue, or grey, paired with a v-neck tee, is a great choice for a minimalist look. For a bolder statement, go for a pop of colour with a tropical short-sleeve button-down shirt.

For women, the Sperry Sailor Boat Shoe in pastel is a stylish option. The satin laces add a luxurious touch to the shoe, making them perfect for pairing with denim cutoffs or linen shorts. For a more casual look, pair them with chino shorts, a flowy tunic, and sunglasses.

The Sperry Crest Boat Shoe is another excellent choice for women, made with lightweight canvas, moisture-wicking material, and a memory foam footbed. They are perfect for pairing with denim shorts and a graphic tee or a printed tank with drawstring cotton shorts.

When styling boat shoes with shorts, it is important to remember that boat shoes are casual footwear, so the overall outfit should lean towards a casual vibe. Additionally, boat shoes are best suited for spring and summer, so it is recommended to wear them from April to September.

Wear with suits

Boat shoes are a tricky shoe to pull off with a suit. The preppy, casual nature of the shoe can make it difficult to style with a more formal look. However, it is not impossible.

Firstly, it is important to note that boat shoes are a spring and summer shoe. They are not designed for winter and will look out of place in the colder months.

When pairing boat shoes with a suit, it is best to opt for a dark suit. A dark brown boat shoe, such as the Sperry Authentic Original, can work well with a dark suit. This is a good way to bring some flair to a race day outfit or a semi-formal wedding. To add a bit of fun to the look, try a pair of colourful or patterned socks.

If you are wearing a suit, it is best to avoid the full preppy look. Boat shoes are a preppy staple and will work with chinos and a polo shirt. However, when pairing with a suit, it is best to keep it simple. Avoid pastel colours, embroidered belts, and other overly preppy accessories.

When it comes to the suit itself, opt for a shorter length. A pair of cropped trousers that skim the tops of your shoes will work well. This is a more modern look and will help to avoid the "college campus" vibe.

Finally, it is important to keep your boat shoes in good condition. A little wear and tear are fine, but you don't want them to look too worn down. Keep a newer pair for more formal occasions and an older pair for casual events and hanging around the house.

Wear with no-show socks

When it comes to styling Sperry boat shoes, one of the most enduring debates in fashion is whether to wear them with or without socks. While traditionally, boat shoes are worn without socks, you can also wear socks with Sperrys, provided you follow a few style guidelines.

If you want to wear socks with your Sperrys, no-show socks are the way to go. No-show socks are cut low so they won't be seen, but they still provide the benefits of wearing socks, like added comfort and blister prevention. They're especially useful if you're breaking in a new pair of shoes, as they can help mitigate blisters and hotspots. No-show socks can also help prolong the life of your shoes by managing moisture and preventing odour- and fungus-causing bacteria from developing. Look for no-show socks that are designed to fit snugly and stay up all day without sliding off your heel. Boardroom Socks, for example, makes no-show socks with a silicone gripper on the inside of the heel to ensure they stay up. Sperry also makes their own no-show socks that are designed to fit well with their shoes.

No-show socks are the best option to wear with Sperrys and shorts, as calf-length socks with shorts are generally considered a fashion faux pas. If you're wearing long pants, like jeans or chinos, you can also wear calf-length socks with your Sperrys, but make sure they're a subtle, dressy pair, like merino wool or Pima cotton socks.

Frequently asked questions