Rolling Pants For Boat Shoes: A Guide To Mastering The Art

Boat shoes are a classic casual shoe trend in the menswear world. They were originally made for sailors and boaters to prevent slipping on boat decks. Over time, they have become popular among non-boaters as well, for both functional and aesthetic reasons. When it comes to styling boat shoes, there are a few things to keep in mind. Firstly, it is recommended to wear them in casual or smart-casual settings, especially during the summer and early autumn. They pair well with jeans, but it is important to avoid excessively tapered or skinny jeans as they can look awkward with the wide-set boat shoe. Cuffed pants or jeans can also complement boat shoes well, adding a summery vibe to the outfit. While boat shoes can be worn with or without socks, it is generally advised to avoid visible socks as they can make the combination look awkward. No-show socks or no-show liner socks are a good alternative to maintain hygiene without compromising style. Additionally, it is important to achieve colour contrast between the boat shoes and the pants to make the outfit more eye-catching and balanced.

Cuff your jeans, but avoid pinrolling

Cuffing your jeans is a great way to show off your boat shoes, but it's important to get the style right.

Firstly, it's best to avoid a pinroll with boat shoes. This is a very specific type of cuff that involves folding the inseam of the leg vertically and then doing a single cuff. It's a great way to show off your shoes, but it's not the best look with boat shoes.

Instead, opt for a simple cuff. Boat shoes are casual footwear, so your jeans should complement this with a casual, nonchalant look. The single cuff is the easiest to master and works with most types of jeans. Simply fold up the leg outwards once, about 5 centimetres (2 inches) above the hem. This works well if your jeans are already the right length, and it can be adapted to look neater or more casual.

The double cuff is another option, but be careful not to make the cuff too big. This involves doing a single cuff and then another, taking off more length.

The mega cuff is a large single cuff of more than 10 centimetres (4 inches). This is a tricky one to pull off and is not recommended for shorter people as it makes your legs look shorter.

The Japanese cuff is another option. This is a big single cuff of 8-10 centimetres (3-4 inches), followed by a smaller single cuff on top.

The summer cuff is ideal for a casual look, and it's meant to look a little messy. Roll the jeans two, three, or even four times in an uneven manner. This works best with roomier fits.

The inside-out cuff is one of the least common cuffs, so it's a great way to stand out. Do a large single cuff inwards, and then a single cuff outwards.

When cuffing your jeans to go with boat shoes, remember to keep the cuffs above your ankles and ensure they're not too bulky.

Wear no-show socks

Boat shoes are a classic casual shoe trend in the menswear world. They are known for their wide-set appearance and bright, contrasting colours. When wearing boat shoes, it is important to avoid visible socks as this can ruin the look and make you seem like a newbie. The solution? No-show socks!

No-show socks are cut very low so that they remain hidden when wearing boat shoes. They are a great way to keep your ankles bare while also maintaining comfort and hygiene, especially in the summer. When choosing a pair, make sure they are low enough so that they are not visible. You can find these socks in most clothing stores, as well as online.

When wearing boat shoes with jeans, it is important to avoid skinny jeans or jeans that are too tapered as this can look awkward in comparison to the wide-set boat shoe. Instead, opt for straight-leg, slim-fit, or wide-leg jeans. Cuffing the jeans can also be a great way to complement the boat shoes, adding a summery feel to your outfit. However, avoid pinrolling, as this will create a tapered appearance that will look unbalanced with the wide-set boat shoe.

No-show socks are a great way to enhance your boat shoe game, keeping your feet comfortable and your ankles looking stylish. So, the next time you reach for your boat shoes, don't forget to grab a pair of no-show socks too!

Choose a neutral colour palette

When it comes to choosing a colour palette for your boat shoes and pants, it's best to stick to neutral colours. Boat shoes traditionally come in darker shades of brown, navy, or neutral leather. These colours are classic, versatile, and will go with almost anything. Navy boat shoes, for instance, pair well with burgundy and grey trousers and are decent with khaki-coloured pants. Brown boat shoes are also a good choice, as they are the most handsome, classic, and versatile colour and will complement nearly everything.

When it comes to pants, you can choose from a variety of colours and styles. For a casual look, you can opt for jeans in lighter shades of blue or more unusual and bold colours. If you're going for a smart-casual look, darker colours like dark blue or grey are more appropriate. You can also try out different styles like distressed jeans with little rips, tears, and frills, or acid-washed and stone-washed jeans. Just make sure to avoid excessively tapered or skinny jeans as they can look awkward with the wide-set boat shoe.

Remember, the key to pulling off boat shoes with pants is to create contrast between the two. Avoid choosing boat shoes that are similar in colour to your pants to prevent them from blending seamlessly together. Instead, opt for colours that complement each other and create a well-balanced silhouette.

Avoid skinny jeans

Boat shoes are a classic casual shoe trend, and they can be worn with jeans, but it's important to get the combination right. One of the key things to remember is to avoid wearing skinny jeans with boat shoes. The jeans should not be too tapered, as this can look awkward when paired with the wide-set boat shoe. Instead, opt for wide-leg, straight-leg, or slim-fit jeans.

Boat shoes are traditionally a summer shoe, given their ankle-exposing uppers, but they can also be worn in early autumn. They are perfect for casual and smart-casual settings, such as garden parties, beach parties, bars, and casual restaurants. When wearing boat shoes and jeans to casual settings, you can be more adventurous with colours and styles. Go for brighter, bolder colours with more contrast between the jeans and shoes. You could also try distressed jeans with rips and tears, or acid-washed and stone-washed jeans. For the upper half of your outfit, a vest with an unbuttoned overshirt, or a simple T-shirt would work well.

When wearing boat shoes and jeans to smart-casual settings, it's best to opt for more neutral colours. A pair of brown or navy blue boat shoes with minimal contrast between the tunneled lacing and the leather upper would be a good choice. The jeans should be a darker colour, such as dark blue or grey, and avoid distressed jeans with rips and tears. For the top half of your outfit, a polo shirt or Henley shirt would work, or an Oxford shirt with a blazer or sports coat for a more dressed-up look.

Remember, when wearing boat shoes and jeans, contrast is key. Boat shoes work best when they stand out from the pants, even just a little. This is true for both casual and smart-casual outfits, but you can be more daring with contrast when going for a casual look. Avoid choosing a pair of boat shoes that is similar in colour to the jeans. For example, dark blue jeans with dark blue boat shoes is not a great combination. Instead, try dark blue jeans with light brown boat shoes. When going for a casual look, go for even more contrast, such as light blue jeans with bright red, yellow, or green boat shoes.

Keep the preppy in check

Boat shoes are a preppy staple, so they'll feel at home with chinos and a polo shirt. But the objective is to look like JFK, not your average American frat guy, so it's important to pump the brakes on pastel colours, embroidered belts, and Croakies. Keep it simple.

Boat shoes have a reputation as the footwear of frat boys and snooty WASPs. To avoid evoking this image, you can mediate the shoe's associations with the rest of your clothes. Don't wear a nautical-striped t-shirt, a pastel-coloured polo shirt (with the collar popped), a blazer, shorts, and Croakie sunglasses.

Boat shoes are traditionally worn in the summer, given their ankle-exposing uppers, but they can also be worn in early autumn. They're perfect for garden parties, beach parties, hanging out with friends, bars, and casual restaurants.

When wearing boat shoes and jeans in a very casual setting, you can go for brighter and bolder colours with more of a contrast between them. Boat shoes can be found in very bright and attention-grabbing colours, and these are definitely an option when you're going casual. You could also go for lighter shades of blue or more unusual and bold colours.

When wearing boat shoes and jeans in a smart-casual setting, it's important to go for more neutral colours. A pair of brown or navy blue boat shoes with minimal contrast between the tunneled lacing and the leather upper would be a good option. The jeans should ideally be a darker colour—dark blue or grey. Avoid distressed jeans, as rips and tears may make them look too casual.

When wearing boat shoes, it's important to avoid visible socks. No-show socks are a great option, as they're low-cut and not visible, but they also feel less awkward and more comfortable than going completely sockless.

Frequently asked questions