The Original Boat Shoe: Sperry Top-Sider

Sperry top siders

The perfect shoe for summer

Imagine having a shoe that's as easy and comfortable to wear as a flip-flop, can be dressed up or down, and has a rich history in American culture. Enter the Sperry Top-Sider – the official shoe of summer.

Whether you're running errands, hitting the beach, or attending a backyard BBQ, there are few shoes better suited to get you through summer than a boat shoe.

And while there are tons of boat shoes to choose from, none is more recognizable than the Sperry Top-Sider, the patriarch and originator of all boat shoes that followed.

History of the Sperry Top-Sider

As with most important advancements, boat shoes were born out of necessity. And as the name hints, the boat shoe has its roots in nautical environments.

After almost losing his life on the deck of a boat, the founder of the Sperry shoe company, Paul Sperry, was determined to make a more slip-resistant sole for himself and his seafaring brothers.

On a cold Connecticut day in 1935, Paul Sperry had a moment of inspiration as he watched his dog run effortlessly across the ice-covered snow. Looking at the pad of his dog's paw, he noticed the multi-directional grooves.

Paul then rushed home and hand-carved a herringbone pattern into a piece of gummed rubber then tested its traction on a piece of polished metal. To his amazement, it stuck like glue.

sperry top sider siped sole boat shoe

Next, he ground the treads off a pair of regular sneakers and glued on his handmade soles. The first Sperry Top-Sider was born.

As you can imagine, a design with such practical implications was soon embraced by all who spent significant time on the water.

In 1939, the U.S. Navy adopted clogs with Sperry's sole design as their unofficial shoe. Sperry even produced five-buckle rubber arctic boots with the same herringbone sole for increased grip on ice.

After prominent individuals, including the Kennedy family, were photographed wearing them while on vacation, the Sperry Top-Sider was brought to the general public's attention.

The launch of Sail Magazine and the Jaws franchise helped bolster America's appetite for nautical style and brought the boat shoe mainstream. Being endorsed by The Official Preppy Handbook solidified the boat shoe as a staple of classic American style.

Boat Shoe Characteristics

While all boat shoe manufacturers produce something a little different, styles get updated, and category lines blur, you can typically expect the following traits in your boat shoes:

Uppers – Boat shoes have a moc-toe design and are traditionally made of leather, although other materials such as cotton are used today. The first Sperry Top-Sider was brown leather, but now a mind-boggling array of colors are available.

Laces – Sticking to the original design, you'll commonly find boat shoes equipped with leather laces. Though some are now available with cotton or synthetic laces.

Eyelets – Two to three eyelet designs are the norm for the Sperry Top-Sider, but single-eyelet versions are available.

Adding more eyelets would bring the tongue of the shoe up too high on the foot, making them less slip-on and warm weather friendly. There are versions like this available, but they're simply labeled as boots.

Wrap-around laces – The Sperry Top-Sider and other quality boat shoes will have a functional 360-degree lacing system. This gives the wearer the ability to cinch the shoe's collar for better security on the foot. You'll find that lower quality boat shoes have non-functional wrap-around lacing in place, just for cosmetic purposes.

Soles – As mentioned in the history section, the calling card of a boat shoe is its grooved or siped sole that's employed to increase traction on wet surfaces. If it doesn't have this sole, it's not really a boat shoe. As far as color, white or off white non-marking soles were the original, but many colors are available now that they're used for casual wear.


sperry top sider boat shoe


sperry top sider boat shoe patina worn

Boat shoes are highly functional, casual wardrobe items and look best when care is approached from a non-fussy angle. In other words, they look better with a little patina.

As you can see from the Before and After photos above, these shoes have to potential to evolve drastically over time. The top image shows my Sperrys after six months, and the bottom their current state three years later.

If you want, you could condition them when new to help with the break-in process. However, I wouldn't use any type of polish, as it'll seem out of place on such a casual shoe.

There's no need for shoe trees with these either. If they do get completely soaked, just stuff them with a little paper towel or newspaper to help speed the drying process.

They're truly the ultimate no-fuss shoe.

How to Wear

In a word, sock-less. If the leaves are on the trees, my ankles are feeling the breeze. Part of the allure of boat shoes is their effortless cool personality.

They're perfect for those days when you're rushing out the door. They slip-on hands free and go with just about any summer attire, with the exception of suits (and even that can work on some occasions).

I have two pairs of Sperry Top-Sider that I wear consistently from early spring until late fall. After the first 60-degree day, it's like I can't go back to pulling on socks and lacing up shoes anymore. It doesn't matter if I'm wearing denim, linen pants, or shorts, some sort of slip-on is my go-to all summer.

NOTE:  Boat shoes are a summer shoe originally intended to be worn without socks. The reasoning is, if it's too cold to go sock-less, it's too cold for summer shoes.

While I do respect tradition, I also wear socks with my boat shoes occasionally. If you aren't comfortable going sock-less, you can opt for no-shows or even wear something with an interesting pattern. It's all up to personal preference.

Everyday casual – Upgrade the summer uniform of khaki shorts, t-shirts, and flip-flops by wearing a short sleeve button up, linen shorts, and your boat shoes.

sperry top sider shorts button up

Summer cocktail party – Just because some occasions call for dressing up doesn't mean you have to feel like a sweaty mess. Pair an unlined jacket with summer-weight chambray or linen pants, and boat shoes. Skip the socks and tie.

sperry top sider blazer

Those cooler days – As I mentioned earlier, once I break out my Top-Siders in early spring, they don't go back into the closet until late autumn. So if a day is unseasonably cold, I layer up and wear jeans as needed, but still skip the socks with my summer shoes.

sperry top sider selvedge denim

Sperry Top-Sider buyer's guide


In my experience, these run true to size. I measure a 12D on a Brannock Device and wear that size in Allen Edmonds, Converse, and the Sperry Top-Sider.


I highly recommend that you stick to the classic design I've shown here. There are a lot of modern versions of this shoe available, with features including synthetic uppers, lugged or wedge soles, and mesh panels on the uppers.

But opting for the original design will ensure their wearability in the greatest number of scenarios and help you get the most mileage out of them.


Though slightly stiff out of the box, I was able to immediately wear them without socks and have never experienced any blisters or discomfort in my boat shoes.

In fact, the very first time I wore a Top-sider, there was so much traffic in Chicago due to the Air and Water Show that a taxi driver refused to let my wife and I into his cab. We were forced to hoof it 2.5 miles at a brisk pace to make it to the train station on time.

I was worried they'd tear up my feet, but to my surprise, I got off scot-free.

To this day, my boat shoes are so comfortable that I've almost walked out of the house numerous times in my leather house slippers because I thought I was already wearing them.

Color choices

sperry top sider boat shoe

When searching out the perfect Sperry Top-Sider, you won't be wanting for options. But if the dizzying array of colors leaves you keen for a little guidance, I can help.

My first pair was dark brown. They go with absolutely everything in my closet, an essential quality when building a versatile wardrobe.

For my second pair, I selected a bright green. These can be worn with most, though not all, of my summer clothes. But that's just fine as I have my go-to brown pair to fall back on.

So if you're in the market for your first pair of boat shoes, I recommend brown, tan, gray, or navy to ensure that you get as much use out of them as possible.

And trust me, once these puppies start to get properly broken-in, you'll never want to take them off.

After you have your first pair in a neutral color, feel free to go bold with the second, third, and maybe fourth pair.

I'm serious, you're going to love 'em.

Where to buy

Even though the Sperry Top-Sider fits true to size, it's nice to buy from a company that offers free shipping both ways just in case you decide you don't like your purchase or they don't fit for one reason or another.

Zappos is my number one choice for online shoe purchases. They have excellent customer service and often upgrade your order to next-day shipping free of charge.

So, are you planning on ditching the flip-flops and embracing the boat shoe? Let me know! 

All the best,


You Might Also Like


  • Reply
    Daniel Ndukwu
    June 5, 2015 at 2:34 am

    Nice one Nate,
    another little tidbit about the history. Sperry’s usually have light colored soles so that they do not scuff the deck of boats.
    Timeless shoe steeped in massive amounts of culture.


    • Reply
      June 6, 2015 at 1:10 am

      Very true, Daniel. I think all colors are supposedly non-marking now, but the originals were indeed white.

  • Reply
    July 19, 2015 at 1:19 am

    Bought a pair of Sperry’s last year. They never quite broke-in and I was left with painful blisters. I’ve not worn those shoes again. I’m thinking about getting another pair but I’m afraid I’ll have the same results. I really don’t want to waste any more money (as I’m a student with high tuition), but I need some comfortable (and stylish) shoes in the summer.
    Do you think I should try again?

    • Reply
      July 19, 2015 at 10:25 am

      Sorry to hear that. Are you prone to blisters with most shoes? I haven’t had a single blister and I’ve broken two pairs of Sperrys, both worn without socks. But I’m not really prone to blisters in any shoe. I think that unless there was some defect in the particular pair you purchased that a new pair would do the exact same thing.

      I would recommend getting some sneakers like the Converse Jack Purcell or some canvas slip ons. Good luck!

  • Reply
    July 26, 2015 at 5:23 pm

    Yep, I’ve used moleskin when I used to get blisters from playing tennis.
    I think I’ll get a pair of Top Siders and see how it goes.
    Thanks Nate.

    • Reply
      July 26, 2015 at 9:06 pm

      Good luck, Ramin! Just wear them around the house for short periods to see if there are any sensitive areas.

  • Reply
    January 9, 2016 at 6:19 pm

    Great write up! I bought the Billfish 3 eyelet version of these but I’m going to take your advice and get the plain version with 2 eyelets. I’m seeing a lot more versatility with those.

  • Reply
    July 25, 2016 at 1:26 pm

    Love the ones in the first picture at the top, the brown shoes by the water. Would like to get them for my fiancee but not sure which ones those are. Can you help me with the style name/color in that photo? Thank you!

  • Leave a Reply

    About Me

    Casual Style 101

    Free style guide