Do You Wear Sperrys with Socks?

Do you wear Sperrys with socks

People hold many differing opinions on what to wear and what not to wear; what fits and what does not fit; what matches and what does not match.

However, it is important you know and wear what matches or suits you in a particular situation to avoid trading your comfort for fashion.

This is because your dressing tells your level of comfort, confidence, status, sense of fashion, and mood. So read along if you’re asking whether you should wear Sperry boat shoes with socks.

Read Also: Do You Wear Crocs with Socks?

Do You Wear Sperry Shoes With Socks?

In the beginning, Sperry shoes were designed for boating, to enable sailors to maintain balance on the deck and avoid slipping. So, at that time, they were worn without socks to prevent the socks from getting soggy and making them uncomfortable.

But these days, Sperry shoes are not only worn for boating. It can be worn for any occasion, as long as it does not rid you of your comfort and confidence. This may require you to match it with socks.

When John Legend, Paul Sperry’s Global brand Ambassador was asked for his opinion about wearing Sperry shoes with or without socks, he said, “It depends on the cut and fit of your pants, and how cool you are.”

In a nutshell, the kind of trousers you put on and your comfort influence your choice of wearing Sperry shoes with or without socks.

Therefore, you can never go wrong when you wear your Sperry shoes with or without socks. The choice is yours; there’s no rule of thumb to that.

Related: 7 Best No-Show Socks to Wear with Sperrys

Read Also: Do You Wear Hey Dude Slip-on with Socks?

Why You Should Wear Sperry Shoes with Socks

To some people, it looks weird to wear Sperry shoes with socks. While to some, it is a fascinating and amazing experience.

It is a perfect idea for you to wear your Sperry shoes with socks for one or all of the following reasons:

1. Durability

Unlike what you have in Crocs, boat shoes are airtight with no holes for ventilation. This causes the accumulation of sweat produced by the sweat glands of the feet. The accumulated sweats cause a buildup of moisture that can lead to odor, discoloration, and peeling of the insole and outsole. This amounts to the extra cost of trying to change the whole sole.

No one loves to spend unnecessarily on things that could have been avoided. That is why wearing Sperry shoes with socks is highly recommended because socks help to absorb sweat on the feet and keep the shoe dry. Thereby preventing odor and increasing the durability of the shoe.

2. Warmth

Socks help to keep the feet warm during cold or low temperatures. This helps to reduce the risk of frostbite, an injury that occurs on the skin during extreme cold weather conditions.

During the cold weather, a thick black or dark-colored sock helps to radiate and absorb heat, thereby keeping the feet warm.

Also, during summer, a light-colored pair of socks helps to keep the feet cool by reflecting heat.

Therefore, having the appropriate type of socks makes it perfect for both seasons.

3. Comfort

Since Sperry shoes are made of leather material, they could sometimes cause discomfort when worn without for a long time. Socks provide a layer between your feet and the shoes. This reduces internal friction and prevents blisters on your ankle. Wearing socks with Sperry generally provides your feet with some level of comfort.

4. Health Purpose

For the reasons mentioned above, wearing socks with Sperry shoes helps to prevent skin injuries and diseases like blisters, frostbite, athlete’s foot, and bacterial and fungal infections that could result from the accumulation of sweats.

Not still sure whether to wear your Sperry shoes with socks? It might be worth it considering the benefits above.

Read Also: 4 Amazing Benefits of Using Shoe Horn

How to Choose Socks for Sperry Shoes

As earlier said, Sperry shoes could be worn both in spring, summer, and almost any other season. Your choice of socks for Sperry shoes can be influenced by these weathers.

For instance, thick dark-colored socks are considered during cold weather because it absorbs and radiates heat and keeps the feet warm. While thin light or bright-colored socks are best for hot weather because it reflects heat and keeps the feet cool.

Another factor that influences your choice of socks with Sperry shoes is the color of your outfit.

You wouldn’t want to look like a village masquerade with poor fashion sense in color combination. So, it is ideal that you pick colors of socks that compliment your outfits.

Besides the factors mentioned above, here is a list of socks for you to wear or not to wear with your Sperry shoes:

1. No-Show Socks

As the name implies, no-show socks are invisible when your shoes are on. The sockless appearance looks fashionable and is ideal for summer. The no-show socks are comfortable with grips at the back that keep them from removing from your feet. These socks and Sperry shoes can go with any pants — long or short.

They come in different colors and patterns, but basically in neutral colors like black and white. Low-cut ankle socks can also be used.

Buy No-Show Socks on Amazon

2. Dress Socks

Unlike the no-show socks, dress socks are visible. If you must wear visible socks, opting for dress socks with your Sperry shoes is a good idea. Unlike some other visible socks like athletic socks, dress socks are thinner and finely woven to give you that comfort you need between your feet and the shoes.

Dress socks with Sperry shoes and shorts may look awkward, but you can always pull through by wearing them with your trousers of any material. Dress socks are also ideal for winter to provide warmth.

Buy Dress Socks on Amazon

NB: Do not wear Sperry shoes with athletic socks!

From a fashion standpoint, wearing Sperry shoes with athletic socks does not compliment in any way. Athletic socks are meant to be worn with athletic shoes and other casual shoes.

Now you can go rock your Sperry shoes stylishly with the appropriate socks.

How to Style Sperry Shoes

Do You Wear Sperrys with Socks?

Ever wondered how you will look when you wear your suit with Sperry shoes? Old-fashioned!

Generally, Sperry shoes are casual footwear that require casual outfits to complement them.

Their simple and smart design makes it possible for them to match with almost all types of pants like culottes, baggy pants, bell-bottoms or flared pants, punk pants, stirrup pants, cargo pants or carpenter pants, fatigue trousers, toreador pants, Jodhpur pants, cropped pants, dungarees and so on. And of course, with the matching t-shirt, polo-shirt, sleeveless blouses or top.

For men, Sperry shoes can be paired perfectly with jeans, chinos, and shorts. While the women can pair them with cropped denim, shorts, khakis, casual dresses, and skirts.

Related: Best Styles of Shoes to Wear with Khaki and Polo Shirt

1. Sperry Shoes with Jean

This is a perfect stylish combo that gives you the casual look you want. You can even cuff the hems of your denim for a more nautical appearance and also to draw attention to your shoes.

Sperry shoes with jeans blend perfectly with dress socks. Unless the hem of the jeans is cuffed, then, no-show socks will be ideal.

2. Sperry Shoes with Chinos

This combo is recommended when you neither want the absolute casual look nor too dressy look.

It is ideal that the color of the chinos contrasts and compliments that of your boat shoes.

For instance, if you put on bright blue chinos, it will be best if you match them with neutral-colored boat shoes.

3. Sperry Shoes with Shorts

This is a matching pair perfect for summer. Of course, this should go without socks or no-show socks.


There is no hard and fast rule as to whether you should wear your Sperry shoes with or without socks.

However, if you choose to wear it with socks, invisible socks (also known as no-show socks) are best rocked or, at most, dress socks when opting for visible socks.

Being aware of the numerous benefits of wearing Sperry shoes with socks, you should rock your Sperry shoes with socks.

In the end, it will not be a question of what matches or not. It all boils down to your comfort and confidence.

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