Wearing Socks With Boat Shoes - Best Style Guide for 2020

Boat shoes are a comfortable and casual alternative to the average sneaker. They’ve always been in style, yet this classic look is really popular in 2020. You may already own some, and if you’re wondering, do you wear socks with boat shoes? you’re not alone.

Whether you’re at a rooftop lounge or on the bow of a yacht, boat shoes offer a functional meets laidback style for you to mix up your look. We’ll go back to the very beginning with how boat shoes came to be, guidelines for wearing socks with boat shoes, and which occasions are appropriate for wearing this style of shoe. Let's sail right into this. 

History of the Boat Shoe

A boat shoe is similar in form to a loafer, with a very interesting backstory. Sources say that boat shoes were initially invented by Paul Sperry. Sperry often had trouble slipping and sliding onboard ships. Sperry realized that his dog didn’t have the same problem, and cut slits in his shoes to mimic the bottom of his pup’s paws (don’t we have so much to learn from man’s best friend?). In 1935, mass-manufacturing began for Sperrys.

Boat shoes are built for practicality, often worn by sailors to prevent them from slipping on deck. They’ve become so popular these days, that most people wearing them would have no idea where starboard is or what chock a block means. Their effortlessly casual and functional appeal has risen them to the height of fashion, and you don’t have to know how to raise a sail to rock a boat shoe.

Do You Wear Socks With Boat Shoes? Why You Should

You definitely can, and it’s recommended that you do. If you decide against socks, you better batten down the hatches, landlubber. There are hazards of going sockless with boat shoes. Why do you wear socks with boat shoes? Because if you don’t, any of the following can happen:

  1. Pooling of foot sweat, which isn’t being absorbed by socks
  2. A powerful odor will radiate from your boat shoes
  3. Blisters and chafing around the heel and sides of the foot
  4. Rapid deterioration of the shoe

So, do you wear socks with boat shoes? If you insist on your feet going commando, it’s possible to ward against nasty odors with different types of deodorizing spray or with baking soda. We still think that's gross, though.  

How Do You Wear Socks With Boat Shoes?

The great thing about boat shoes is that they’re versatile. They basically go with every type of sock, provided that you match your outfit correctly. Let’s dive into our top sock picks for boat shoes.

The Pretend Commando: Invisible or Barely There Socks 

If you’re heading to the beach, strolling around in the summer, or in any other warm conditions, you might want to appear sockless, or wear socks that are minimally visible. No show socks, sometimes referred to as loafer liners, only go part of the way up your foot. You’ll barely be able to see them inside your boat shoes. These socks will keep your feet dry and legs nice and airy, plus they’ll pair well with shorts or capris.

Classic and Sleek: Black Dress Socks 

If the weather is a bit colder, or you’re planning on wearing long pants with your boat shoes, black dress socks will work with anything from jeans, to chinos, too khakis. Dress socks are typically designed using a thinner and finer woven material, so your feet and legs will stay warm. The neutral shade of black will work with most outfits, and dress socks will elevate your look (as opposed to crew socks or an everyday sock).

Bright and Bold: Socks to Match Your Personality

You may have come across style blogs and fashion gurus advising against wearing socks that are colorful or patterned with boat shoes. Let us tell you why the rule deserves to be broken. First of all, rules are stuffy. Second of all, why pretend to be anyone but yourself? 

Pair a neutral outfit and boat shoes with a fun pair of socks for a splash of color. That way, you’re not wearing clashing colors, but adding life to your look. If you're even more courageous, complement your bright outfit with matching socks in the same shade. Just prepare for all eyes to be on you, and you're golden.

Subtle Yet Fun: If Bright and Bold Isn’t Your Jam

You’ve got options if you feel like showing some sock, but don’t want to venture too far out of the ordinary. Stripes can help you show off your boat shoes, by drawing the eye straight to them. Try vertical stripes, ideally in a skinnier variety. As a simpler pattern, Polka dots won’t clash with boat shoes. You’ll want to stick to smaller dots, so that you’re not overwhelming the rest of your outfit. 

Choosing Your Sock Colors

We made up a chart that pairs all the most common boat shoe shades with the colors that work best for them. You’re welcome! You can learn more about complementary colors in our wearing socks with Sperrys guide

Boat Shoe & Sock Color Guide
Boat Shoe Complimentary Sock Colors
Brown  Blue, White, Grey, Red 
Tan  Navy, Blue, Purple, Black
Grey Purple, Teal, Turquoise, Yellow
Black  White, Light Blue, Light Purple, Grey, Red

Consider the saturation and shade of the colors while choosing your socks. If your boat shoes are a muted color, you’ll want to choose the same for your socks. And if the colors of your boat shoes are brighter, the same logic applies.

Our Top Socks & Boat Shoes Looks

Lean into the preppy vibe: Think sailing in the Hamptons during a summer that never ends. Try pairing your boat shoes with a polo shirt, khakis, and a leather belt. Slip on your no show socks and you're ready to roll.

Wear them with your jeans: Boat shoes and jeans are a natural fit togetherthe same type of casual classic. With neutral blues like this, you could go with black dress socks, bright or patterned socks, or stick to no show. 

Wear them with cut-off or rolled-up pants to really emphasize the shoes. This clean look is made for no shows. Otherwise you might have an awkward patch of skin between where the socks end and the pants begin.

Wear them for a business casual vibe: to relax your look a bit at the office (if this kind of dress code is allowed, anyway). If you dare, make a statement with some red socks. Otherwise neutral dress socks or no shows would work.

Want more style tips? Check out our guide to wearing socks with Sperrys

Learn Some Suave Ties 

Leaving your boat shoes untied is a hazard. We’re all for effortlessly stylish vibes, but not tying your boat shoes looks careless and you may end up tripping over them and falling on your face. Definitely not the cool you’re going for. You can add flair to your boat shoes, just in how you tie them. Try these out:

  • Stay on theme with a fishtail knot. Start by pulling the laces through the eyelets vertically. Cross the laces, and bring each side over the opposite side, then repeat three times. Tighten any extra, and then stick the ends behind. 
  • Go traditional sleek with a surgeon’s knot. Lay each side over each other so that they overlap, then form a loop. Pass each side through the loop three times. Just pull tight, and you’re finished!
  • Get creative with a barrel knot. To tie a barrel knot, you fold the lace into a loop. Then, wrap the lace around the loop five times. Thread the lace through the loop, and pull it while pushing the knot to finish. 
  • Add some artistry with a chain knot. Make a loop, with the lace pointing to the front. With the other hand, make another loop. Push the second loop into the first loop from the back, pull to tighten, and repeat. After three repetitions, tuck the lace through the knot, then stick the ends of the chains into each other. 
  • Graduate to a tassel knot. Cross your laces into a square knot, and hold one lace to form a loop. Wrap the lace back around the loop, then tuck in the end. 

When Do You Wear Socks With Boat Shoes?

Boat Shoes Q & A

  1. Do you wear socks with boat shoes in the wintertime? The all round answer is no. You don’t want to be the person who wears summer shoes when it’s snowing outside. If you live in a seasonal climate, they’ll have to go on hiatus when off season. 
  2. Can you wear boat shoes when it’s raining? You can, but this will damage them.
  3. Do you wear socks with boat shoes to exercise? Boat shoes and any kind of exercise don’t mix. Even with socks on to absorb the sweat, they’d be falling off during a high intensity workout. 
  4. Can you wear boat shoes to go hiking? Even if it’s a relatively easy hike, you may get blisters. Best stick to runners.
  5. Do you wear socks with boat shoes when you’re wearing a suit? Even dress socks with boat shoes would not be enough to make them formal. No boat shoes with formalwear.

When It’s Always a Good Call Wearing Boat Shoes

Ok, so you can’t wear boat shoes in every situation. Same goes for any of your favorite shoes. You can rock boat shoes on the beach, especially at beach wedding. They're really great for travelling, especially on airplanes. Think any casual location and outdoor activities that aren't strenuous (like talking a stroll down the boardwalk). 

Treat your boat shoes right by wearing them with a great pair of socks. Just switching up your socks can give any outfit featuring boat shoes a new edge.