Why The World Has Loved Sperry Since 1935


Since I was young we have always had a cabin in Northern Minnesota on a beautiful lake.  With the cabin came the boats we’ve had over the years; we’ve had fishing boats, speed boats, old boats and new boats, but the one thing that never changed was the shoes my grandpa wore on the water.  For as long as I can remember he has always had a pair of classic Sperry’s , tan and leather (like the ones pictured above.)

I never thought anything of it, I just assumed this is what all men wore, especially while on the water.  They looked right at home, whether we were taking the boat to a nice restaurant on the lake for dinner or he was teaching me how to filet a fish, his shoes just looked right.

As I got older I realized not all men make sure great decisions and I see far too many wearing flip-flops places other than the beach, and even there, I’d still vote Sperry’s.

We know it’s still cold outside, but here’s to get you thinking of summer.  This is our review, thank you letter and proclamation for Sperry Top-Sider, the king of all boat shoes.

The History of Sperry Top-Sider


Paul Sperry was an innovator, a slippery-boat-deck-life-saver, and most of all, a man of impeccable style.  As an avid sailor who once came close to losing his life due to a slippery deck, Paul Sperry spent years trying to make the perfect shoe to help you keep your feet on the ground while hitting the big waves.

In 1935 while trying to perfect his latest shoe design, Paul Sperry witnessed something that would change the shoe game forever: he watched his dog run effortlessly across the ice.  This small, but very important, thing was what gave Mr. Sperry the idea to add some grooves to the rubber soles of his boat shoes.  This was the day the official Sperry Top-Sider shoe was born.


Sperry quickly gained recognition and became the top shoe amongst sailors in the US, and was named the official shoe of the navy during World War II.


While the shoes had been popular amongst sailors for years due to practical reasons, in the 1960’s Sperry gained even more notoriety.  However, this time people cared less about the non-slip features and more about the polished look of a Nautical man.  After JFK made Sperry’s part of his iconic style, the trend took off and has (thankfully) never quite died down.


The shoes continued to grow in both popularity and function as time passed, and by 2007 Sperry was known as the #1 selling men’s shoe in US department stores.  Whether it’s the style or the purpose you need them for, you are in good company.

Which Sperry Boat Shoe Suits You Best?


The Authentic Original Boat Shoe is by far the best known and my personal favorite.  But not everyone loves brown leather, especially on the water.  For those who want to add some color to their feet Sperry has more models of boat shoes than anyone could ever need.

Whether you are looking for furry camo or neon bottoms, Sperry’s got you covered.  Here are a few of our favorite boat shoes.

Color Pop Gore Boat Shoe, $90.


Color Pop 2-Eye Boat Shoe, $59.99


Anchor Tattoo Canvas 2-Eye Boat Shoe, $90.


Authentic Original Burnished Boat Shoe, $69.99



Authentic Original Navy Boat Shoe, $85.

Authentic Original Boat Shoe, $85.

Camo Barrel Lace Boat Shoe by Jeffrey, $74.99


More Than Just Boat Shoes…


We love Sperry first and foremost for their boat shoes, but we love them for more than just that.  Sperry also has great boots, casual sneakers, oxford lace-ups and loafers.  They really are your one stop-shop for all footwear occasions.  Here are some of our favorite boots, shoes and other things this iconic brand has been able to woo us with.

Cold Bay Duck Boots, $140.

Gold Cup Authentic Penny Loafer, $150.

Cloud Logo Canvas Harbor Oxford, $90.

Salt Washed Twill Striper CVO Sneaker, $60.

Sperry Coupons, Sales and Promo Codes


Sperry Top-Sider regularly offers sales, promo codes and coupons to help you save a little money.  While the coupon above is a little outdated, new promotions roll around regularly, so if you see a pair you want just keep your eyes peeled for the next time Sperry offers a little discount.

However, if you don’t feel like playing the waiting game, there is always the sale section along with numerous other websites that offer great discounted deals on Sperry’s.  Click here to check out the Sperry Sale Section or check out our links below for some great sites that will save you some cash.

6PM.com:  If you have never heard of 6pm.com, it is a great bargain site to find amazing deals on shoes.  Pictured below are just a few of the sale prices we found, click here to see their entire assortment.


Zappos.com is always a great place to find a good deal.  Shopping for Sperry’s is no exception.  Below are a few of the great deals we found at Zappos, click here to see the rest!



Our Final Review of Sperry Top-Sider


We here at Life, Tailored have been fans of Sperry shoes since we put on our first pair years ago, and we will continue to be fans until we’re too old to walk.  Classic style is always classic, and these amazing shoes aren’t going anywhere.  If you are one of the few that has never owned a pair of Sperry’s, don’t let another summer go by before you learn what you’ve been missing.

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