How to Break in a Pair of Sperry Top Siders Quickly: 11 Steps (2024)

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Co-authored byMoe Draper

Last Updated: October 30, 2021ReferencesApproved

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1. 1

   Fill a spacious container with about 6 inches (15cm) of warm water. The easiest way to do this is to simply run some water into your bathtub as though you were about to take a nice relaxing soak. If your home doesn’t have a bathtub, you could also use a large bucket or a plastic or rubber storage container, so long as it’s watertight.^[1]

   • Whatever container you end up using should provide enough room for you to stand in with both feet comfortably.
   • Assuming you have neither a bathtub nor another suitable type of container at your disposal, you also have the option of searching for a natural body of water to go tramping through, or wetting your shoes thoroughly with a garden hose or faucet.
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   Add some sea salt if you want to give your shoes a more weathered look. The exact quantity you put in will depend on the amount of water you’re working with. Aim to use about 1 tablespoon of salt for every ¹⁄₄ gallon (0.95L) of water in your container. This will give you a salinity of about 3.5%, which is roughly the same as the water in the ocean.^[2]

   • You can pick up a bag of purified sea salt at the supermarket for just a few dollars.
   • Incorporating salt into your soaking water will simulate the conditions of wearing your Top-Siders in and around the sea, which is perfect if you’re going for an aesthetic that’s more veteran seaman than preppy yacht club.^[3]

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   Put on your Top-Siders and lace them up tight. Slip into the shoes and pull as much slack out of the laces to make sure that they’re nice and snug on your feet. The tighter you make them now, the more they’ll loosen up once you get them wet.^[4]

   • Don’t wear socks with your boat shoes (unless you enjoy the feeling of soggy feet).
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   Stand in the water with your shoes on until they’re wet all the way through. Canvas and textile shoes will begin sponging up water right away. It may take a few minutes for leather, which has natural water-resistant properties, to become fully saturated. As you stand in the container, rock forward onto your toes and backwards onto your heels to stretch the material through its full range of motion.^[5]

   • Watch your step when climbing into your soaking container. Even though boat shoes are made for wet wear, accidents happen.

   Alternative: Place your Top-Siders in the water by themselves and leave them to soak for 12-24 hours, then fish them out and put them on while they’re still wet.^[6]

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   Towel-dry your Top-Siders to remove excess water. Step out of the container carefully, allowing the water that’s collected inside the shoes to drain out as you do. Then, pat the upper part of the shoes all over with a clean, dry towel to wick up the remaining moisture on the surface. They don’t need to be bone dry—just dab them until they stop dripping.^[7]

   • It’s a good idea to put down an absorbent layer, such as a bath mat or second folded towel, to avoid covering the floor with standing water.
   • Some Sperrys (particularly textile models that have been dyed to deep shades) aren’t as color-fast as others. If possible, select a dark-colored towel that won’t show signs of staining in case of bleeding.
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   Wear your shoes around as they air dry to let them conform to your feet. For best results, go for a short walk or do some simple exercises to introduce more movement to the damp material. Boat shoes are designed to dry quickly, so you shouldn’t have to wait long. In no time at all, your brand-new Top-Siders will soften up and take on an organic lived-in look, like you’ve owned them for ages.^[8]

   • If you’ve got other things to do, or just don’t particularly feel like wearing wet shoes, leave a wooden shoe tree in your Sperrys while they air out instead.^[9]
   • Leather expands when it gets wet and shrinks as it dries. Together, these two reactions will result in a unique fit that feels tailor-made for your feet.
   See Also

   How to Stop Blistering and Slipping in Loafers and Boat ShoesSocks With Boat Shoes: How to Pull Off the Look5 Ways to Avoid Blisters and the Best Way to Treat Them

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1. 1

   Make sure you buy your Top-Siders in the right size. The key to getting the perfect fit is to first make sure that your shoes are sized appropriately. Most Sperry footwear tends to be true-to-size, but it won’t hurt to try on a pair on either side of the size you ordinarily wear, just to be sure.^[10]

   • Sperry’s sizing experts recommends buying leather shoes a half-size smaller than your normal size. Keep in mind that leather shoes will loosen up a bit with regular wear, so don’t be put off if they feel just a hint too snug at first.^[11]
   • A good rule of thumb is that there should be about ¹⁄₂in (1.3cm) of space between the top of the shoe and your big toe when you’re standing normally.
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   Opt for leather over canvas or textile shoes for a more custom fit. Woven fabrics are typically more comfortable straight out of the box, but don’t change shape the way that leather does. Genuine leather, on the other hand, will conform to your feet more and more over time, eventually fitting like a glove.^[12]

   • If you decide to go with a canvas or textile model, stick with your tried-and-true shoe size, since they won’t relax as much with age.

   Tip: While all Sperry’s shoes are water-friendly, canvas kicks have a bad habit of absorbing and holding onto moisture. But worry not—you can easily waterproof a new pair of canvas shoes yourself once you get them home.

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   Break in stiff, unyielding spots manually. Spend some time working problems areas like the toe box and the back of the heel by hand. Take hold of the material and knead, flex, twist, and stretch it in different directions until it begins to offer a little more give. This kind of special attention can enhance the convenience of a new pair of Top-Siders before they ever touch your feet.^[13]

   • Sperrys are known for their resilience and durability, so don’t be afraid to get rough with them.
   • Insert shoe trees into your Sperrys whenever you’re not wearing them will also prevent them from returning to their original manufactured shape.
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   Use leather conditioner to further soften and protect leather shoes.^[14] Massage a small amount of conditioner into each shoe using smooth, circular motions, then wipe away the excess with a lint-free cloth. Afterwards, wrap the shoes separately in pieces of newsprint and stash them in a cool, dry place while the oil sets in. You’ll feel the difference after just one treatment.^[15]

   • Gentle natural oils like mink and neatsfoot oil are also safe for use on most types of leather.^[16]
   • In addition to giving the leather uppers a warm, buttery touch, a quality conditioner or oil will also help safeguard your boat shoes from the damaging effects of prolonged exposure to moisture and dry air.
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   Remove sharp thread ends on the inside of the shoes to keep them from poking. Throw your Top-Siders on over your bare feet and feel around for threads that stick out further than they’re supposed to or places where the stitching has come loose. When you come across a troublesome thread end, snip it off with a pair of scissors, or pull it free by hand, if it’s also come undone at the opposite end. No more scratchy, irritating sensation when you walk.^[17]

   • Be careful not to cut any stitches that are still intact. Doing so could cause your shoes to begin coming apart prematurely.

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