Rolling Khakis With Boat Shoes: The Perfect Summer Look

Boat shoes are a popular choice of footwear for many, but what about pairing them with khakis? And should you roll up your khakis when wearing boat shoes? Well, it turns out that this combination is entirely possible, and even recommended by some. The key to pulling off this look is all in the cuff. A simple single or double cuff will do the trick, but be sure to avoid excessive rolling that could turn your pants into clam diggers. The aim is to show off the distinctive detailing of your boat shoes, so make sure the cuffs graze the tops of your shoes. As for the socks, it's best to avoid visible socks with this combination. No-show socks or sock liners are your best bet to maintain the casual elegance of this look. So, if you're thinking of pairing your boat shoes with khakis, roll up your pant legs and get ready to set sail in style!

Cuffing your khakis

There are two main ways to cuff your khakis: the single or double cuff. For the single cuff, simply fold the bottom of your trousers once, upwards and towards your knee, creating a thick horizontal cuff just above your ankle. For the double cuff, fold the bottom of your trousers once more, in the same direction, to create a second, thinner cuff.

The single cuff is a more casual look, whereas the double cuff is more formal. If you're going for a smart-casual vibe, the double cuff is probably your best option. However, if you're wearing boat shoes, you're probably aiming for a more casual look, so the single cuff might be preferable.

When cuffing your khakis, it's important to avoid overdoing it. You don't want to create a look that's trying too hard. One or two rolls will do the trick. Anything more will make your trousers look like capris.

Additionally, make sure your trousers are the right fit. Boat shoes tend to work best with slim or regular-fit trousers. Avoid skinny trousers or anything too loose around the calf.

Choosing the right socks

When it comes to choosing the right socks to wear with boat shoes and khakis, there are a few options to consider. Firstly, it is important to note that boat shoes are typically considered casual footwear, and the general consensus is that they should be worn without visible socks. This is because wearing socks with boat shoes is associated with a lack of style consciousness and can detract from the overall aesthetic of the shoe.

However, this doesn't mean that you should forgo socks altogether. No-show socks, which sit below the line of the shoe and are invisible, are a popular choice. These socks serve a functional purpose, providing comfort and helping to prevent blisters and irritation. They also help to keep your feet dry and can reduce odour—a common issue with boat shoes. When selecting no-show socks, opt for neutral colours such as white, black, or grey, to ensure they remain discreet. Silicone grips on the interior of the sock can also help to keep them in place and prevent slippage.

If you want to wear visible socks, it is important to choose the right type and colour to complement your boat shoes and khakis without drawing too much attention. Crew-cut socks in muted, pastel colours are a good option. Light brown and grey tones, as well as classic white, can work well. Avoid athletic socks at all costs, as these are too casual for boat shoes and will detract from the overall look.

When wearing socks with boat shoes and khakis, it is also important to consider the length of your trousers. The distinctive detailing of the boat shoe should be visible, so opt for a slightly higher break that skims the tops of your shoes. If your trousers are long, you can roll them up a little, but avoid rolling them too high, as this can look untidy.

Styling with jeans

Boat shoes are a great addition to any outfit, and they look particularly good with jeans. Here are some tips on how to style jeans with boat shoes:

• Cuff your jeans: For a more effortless, nautical look, try cuffing the hems of your jeans. This will complement the look and draw attention to your boat shoes.
• Keep it casual: Boat shoes are casual footwear, so they look best with a polo shirt, button-down shirt, short-sleeve henley, or guayabera on top.
• Choose the right jeans: Boat shoes pair well with tailored, straight-leg, or tapered jeans. Avoid wide-leg jeans, as they can look funny with the small moccasin toes of boat shoes.
• Contrast colours: Choose a darker shade of boat shoes than your jeans to create a contrast. This will make your boat shoes stand out.
• Break out the blazer: You can even wear boat shoes with a blazer for an interesting twist on business casual. Just make sure to dress down the rest of your outfit.
• No socks: Boat shoes are typically worn without socks. If you're concerned about sweat or odour, opt for no-show socks or a terry cotton liner.
• Beige blazer, blue jeans, and beige leather boat shoes.
• White crew-neck t-shirt, blue jeans, and dark brown leather boat shoes.
• Brown shawl cardigan, blue jeans, and dark brown leather boat shoes.
• Beige corduroy shirt jacket, blue jeans, and dark brown leather boat shoes.
• Multi-coloured plaid long-sleeve shirt, blue jeans, and dark brown leather boat shoes.

The preppy look

Boat shoes are a staple of the preppy look, but it's important to style them right to avoid looking like a "guy who just got kicked off his college campus". Here's how to achieve a preppy look with boat shoes and rolled-up khakis:

Choose the Right Boat Shoes

Boat shoes are moccasin-like shoes with a low cut, hand-sewn construction, soft white non-skid rubber soles, and distinctive lacing. When choosing a pair, opt for leather over canvas as it's more durable, snazzier, and can be paired with slightly dressier clothes. Go for a darker brown colour, as it's the most classic and versatile option.

Roll Your Khakis Appropriately

When wearing boat shoes with khakis, make sure your pants break a little higher than normal, just skimming the tops of your shoes. This way, you showcase the distinctive detailing of the boat shoes. If your pants are on the longer side, you can roll them up a little, but avoid going overboard and entering clam-digger territory. Remember, a little roll goes a long way, especially when you're nowhere near the dock.

Complete the Preppy Look

The boat shoe is a preppy staple, so feel free to pair it with chinos and a polo shirt. However, to avoid looking like a stereotypical frat guy, steer clear of pastel colours, embroidered belts, and Croakies. Keep it simple and sophisticated, perhaps drawing inspiration from the likes of JFK. You can also add a blazer, but make sure to dress down the rest of your outfit to maintain the smart casual aesthetic.

Additional Tips

• While boat shoes are traditionally worn without socks, you can opt for no-show socks to avoid the issue of sweaty feet and odour.
• Play around with different ways to tie your laces. Rawhide laces can come undone easily, so consider using a different knot for both functionality and a change in style.
• Boat shoes are best worn in warmer weather and with lightweight pants or shorts.
• Boat shoes are casual footwear, so pair them with nicer casual clothes such as polo shirts, button-down shirts, or henley shirts.

Boat shoes and formality

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. However, their practical non-slip rubber sole and unique hand-sewn upper design soon drew attention from all kinds of shoe wearers. Today, boat shoes are commonly worn by boaters and non-boaters alike, both for functional and aesthetic reasons.

When it comes to formality, boat shoes are considered casual footwear. They are not meant for black-tie affairs or very formal events. Instead, they are perfect for business casual environments, dates, beach trips, travel, and casual occasions. Boat shoes can add a touch of style to your outfit without going overboard.

In terms of pairing, boat shoes are quite versatile. They look great with jeans, especially if you cuff the hems for a more effortless, nautical look. Boat shoes also go well with colourful chinos, as long as the colours contrast to balance things out. For example, pair bold red or green chinos with a more neutral-coloured shoe, like brown.

Boat shoes are also a perfect combination for summertime wear with shorts. Just make sure the shoes are not too attention-grabbing, as you don't want the look to be overwhelming.

One important consideration when wearing boat shoes is to avoid visible socks. This is a big no-no and can ruin the look. However, no-show socks or ankle socks can be worn for comfort without being seen.

Boat shoes should also be avoided with suits, as they don't fit the formal look. If you want to dress them up a little, opt for dark wash denim and a blazer for a business casual twist.

In terms of colour, boat shoes come in various options, but it is recommended to go with a darker brown as it is the most classic, versatile, and handsome colour. It will go with almost everything. Navy is a close second in terms of versatility and can look great with burgundy and grey bottoms.

When it comes to rolling up khakis with boat shoes, it is generally considered proper to cuff the khakis. This adds a touch of casual elegance to the outfit. However, some may prefer flat-front khakis without cuffs, especially in more modern or urban settings. Ultimately, it is a matter of personal preference and style.

In conclusion, boat shoes are a versatile and casual shoe option that can add style to your outfit. They are perfect for a variety of occasions, from beach trips to business casual environments. Just remember to avoid visible socks and pair them with the right trousers or shorts to complete the look.

Frequently asked questions