Long Term Review, Sperry, Stitched Footwear

Sperry Top Sider Gold Cup: Five Year Review


  • Cost: $160 MSRP
  • Pros: Great value when bought on sale, classic design
  • Cons: Lined interior not great sockless, tough competition at MSRP



The Sperry Top-Sider has been a staple of those who want to look like they could jump on their yacht at any moment – even if the closest they’ve been to a large body of water is Point Place in Toledo, Ohio. Most people will point to 1935 as the year the Top-Sider was introduced, but that isn’t exactly true. That was when Paul Sperry first put a siped sole on a shoe. Supposedly inspired by the grooves in his dog’s paw that managed to stay on deck while he slide overboard. However, that shoe was closer to the current CVO than the Top-Sider we know today. The leather, moc-toe version didn’t come around until a few years later.

Sperry positions the Gold Cup as their higher end line (though not quite up there with the Rancourt-made “Handcrafted in Maine” line). The differences include not just better materials, but minor styling details such as a two-tone outsole, a lined interior, and gold plated eyelets.

These particular Top-Siders are just over 5 years old, and I’ve worn them well over 200 times. They have seen miles and miles on city streets, trips to the beach, and more than one unplanned multi-mile hike.

Unfortunately, a few days ago they met their match. A few minutes with a puppy who thinks unreplaceable leather laces are a better snack than bacon.

Sperry Top-Sider Logo
Sperry Logo


If you need to have it now, you can get them right from the source for $159.95. If you have flexibility in colorway you can regularly find them for half of that at places like Nordstrom Rack. The pair in this review came from a Clear-The-Rack sale for right around $35 dollars.


If the upgrades don’t sound worth it to you, they are available in just about any color for $94.95. Again, if you don’t care about finding the exact right color, you can find them at Nordstrom Rack for a lot less.

Sperry Top Sider Gold Cup Side
Sperry A/O Gold Cup in Grey


Sperry isn’t the only company that makes a boat shoe. You can find them for $15.99 from Kohls or you can get custom made shell cordovan Rancourts for $745 dollars – but when it comes to who makes the most classic design there is no competition. Good or bad, when you think of someone wearing boat shoes, you think of someone wearing Sperrys.

Up front, the shoe sports a hand-sewn moc toe, held together with an abundance of glue that sticks up beyond the leather in multiple spots. The trade off is that, unlike shoes that skip this part of construction, years later the moc toe has held it’s shape without the thinner part of the leather bending over with time. Moving back, the standard A/O means a quarter with a two-eyelet design. The Gold Cups all feature gold plated eyelet holes as well.

The navy blue laces appear to run a 360 loop around the shoe, but this is mostly just for show. [Side Note: Sperry made a nice video on how to replace the laces, however in every pair I’ve owned the laces are sewn flat at the vamp and can’t be removed from the back] At the rear there is a strip of contrasting leather that meets with another area of hand-stitching at the back of the shoe.

The sole of the shoe is a two-tone design. On top a navy portion was designed to mimic a traditional welt, and is glued to an off white outsole. Looking at the sole you’ll see 360 degree stitching holding the outsole to the upper.


Apart from a bit of unevenness on the moc-toe, which is part of the hand-sewn design and is done on purpose, stitching is even. It has held up well with only a very small number of lose threads in high wear areas near the back of the shoe.

The leather on this pair started off as a very even gray but has faded a bit over the years. Now, it’s almost more brown than gray. While any patina you develop yourself always has a certain charm, it’s impossible to overlook that this hue results in them looking dirty rather than well-worn most of the time.

While not overly deep on any part of the shoe, creasing of the leather is visible on every panel. This color leather does an amazing job at hiding scratches. Unfortunately, the navy portion of the outsole scrapes through to an orange color. Don’t expect it to stay visually appealing in the long-term.

Sperry Top Sider Gold Cup Side
Sperry Top Sider A/O Gold Cup Rear

Size, Fit, & Comfort:

Out of the box, Sperrys generally fit true to your Brannock size. However, the leather on these shoes tends to stretch more than most other pairs. Going with your true size might ultimately end up leaving you swimming in the shoes.

As a rule of thumb I would suggest going down ½ size for Sperry Gold Cups. Of course, if you have the chance to try them on I would strongly encourage it. Sperry uses various factories in different countries to manufacture their shoes, and each factory uses a different last. These different lasts, or shape the shoe is built on, can result in two shoes fitting you differently, even if they are labeled the same size. While the normal last is not particularly wide-foot friendly, Sperry makes most of their Gold Cups in both D width (which Sperry calls “M”) and E width (which Sperry calls “W”). Wide models are much harder to find at a discount though.


A Size Comparison of Reviewed Shoes Can be Found Here

Comfort is where you see the main differences between the regular line and the Gold Cup. The Gold Cup features a small amount of padding along the entire insole, which can be a real difference maker for those who are wearing their boat shoes to walk further than the bow to stern of a dingy. The other major change is the lamb-skin liner that covers the interior of the shoe. This liner is a bit of a mixed bag. It is certainly nicer to the touch when compared to no liner at all, however the additional layer decreases breathability and may make no-sock wear a bit more swampy than you would like in the summer.

Despite the upgrades over a standard pair, these shoes are not great for all-day wear. Especially if you plan on putting some miles in. The additional padding will compress after an hour or two and you’re ultimately left walking on a slab of rubber.

Sperry Top Sider Gold Cup Sole
Sperry Top Sider A/O Gold Cup Sole


While there is a bit of variance in the gold cup line, generally the leather on the exterior of the upper is a full-grain chrome-tanned cow leather. The leather holds up to abuse well. It takes scuffs in stride, though as mentioned above does lose some pigment over several years. Other components on the exterior of the upper include metal eyelets to help prevent the raw-hide laces from ripping through. Inside the shoe is a lamb-skin liner that begins soft and remains so through the life of the shoe. In between the lining and the upper, the eyelets have a plastic backing to help prevent rips.

Below the line is a glued down Ortholite insole that has stood the test of time. In this pair, the insole is still soft and springy when you put your foot in. That being said, an open-cell structured insole, such as what Ortholite uses, will always compress throughout the day. Underneath the insole is a moccasin construction, which means the leather from the upper wraps underneath your foot. That same leather from the uppper is then glued and stitched to a two layer rubber outsole. While not mentioned by Sperry, my experience says the Gold Cup sole lasts longer than the standard pair.

Sperry Gold Cup Side
Sperry Top Sider A/O Gold Cup Side


There is essentially no traditional break in for these shoes. They come out of the box soft and pliable. The leather will stretch and mold to your feet over time so the comfort does increase with wear. Eventually they reach the point where they can act more as slip-on shoes.

While the shoes themselves might not break in much, the same can’t always be said for the person wearing them. If you’ve never worn leather shoes without socks, the first few wears might rub your ankle raw. If this happens to you, a band aid or moleskin can help for the first few wears.

Ease of Care:

These shoes are just about as easy to care for as is possible. The leather itself is tough enough that if it gets dirty a simple wipe down with a wet cloth will get almost everything off. Beyond that, conditioning every 6 months or so with something like Bick 4 will help keep your leather soft and healthy.

While it is possible to resole a Top-Sider, the cost of the resole will typically run about the same price as buying anew pair (between $50 and $100 depending on which city you live in). Further, Sperry does not sell their soles to repair shops so what you get back will be slightly different than what you received new.

As with any moccasin constructed shoe, the number of resoles will depend on the skill of the person doing it. With no factory resole option, don’t expect to get more than one or two, if you go that route.

Sperry Top Sider Gold Cup
Sperry Top Sider A/O Gold Cup


If they style fits your needs, there are few shoes out there that offer better value for the dollar than the Sperry Top Sider Gold Cup. They go with a variety of outfits and last for years. At the same time, they are affordable enough that you can feel comfortable wearing them to a place where they might be banged up a bit or buying a color that might not be the most versatile.


While they won’t give the support or comfort that a sneaker will, and don’t have the long lasting nature that a goodyear-welted boot or oxford brings, it is hard to deny that the Sperry Top-Sider is a classic shoe that represents a great value proposition. The Gold Cup version offers a fairly substantial upgrade over the base model. And, when found on sale, come in at a similar price. As long as you can live with the loss of breathability from the liner, it should be a no-brainer to pick up a pair.

Do you agree? Do you disagree? Let me know in the comments below