Long Term Review, Sperry, Stitched Footwear

Sperry x Band of Outsiders: 100 Wears In. Does it Hold Up?


  • Price: $150 MSRP [no longer available]
  • Pros: Great twist on classic design
  • Cons: Horrible materials


Sperry Topsider Logo


Sperry as a company has a collaboration catalog that puts everyone apart from Nike to shame. Sperry has partnered with everyone from movie studios, both Quoddy and Rancourt, Patta (before New Balance), Rains, Barneys, J. Crew, and more. However, one of the most sought-after collections was the Sperry x Band of Outsiders Topsider collabs.

Under their old ownership, Band of Outsiders focused on taking preppy staples such as blazers, oxfords, and wool pants and updating them for the 21st century. This focus led to multiple releases with Sperry, itself one of those staples.

This pair was from the very last drop before Scott Sternberg sold the company in 2015. Since that time, Band of Outsiders have become increasingly streetwear focused. Moving away from preppy staples, this shoe is pretty much the swansong for the original brand.

Does it hold up? Or did Scott just try to take one more cash grab on his way out? We’ve worn this pair just over 100 times to give you an answer.

Sperry Band of Outsiders
Sperry Topsider x Band of Outsiders


Initially, this Sperry x Band of Outsiders shoe seems pretty familiar. Overall, it is mostly a classic top sider. This design means things like the classic moc-toe is there, just slightly longer cut than most other brands. However, after a split second you start to notice the differences in the shoe.


Most obvious is that the traditional laces have been removed, and have been replaced with tassels. These tassels, bright green in color, are the same thickness as the laces that normally come with Sperrys. This means that, even with wear, there is very minimal splaying at the ends, and the color has stayed similar to when they were first pulled out of the box. Interestingly, unlike most other tassel loafers, the shoe still features metallic eyelets, which are usually only in place to prevent tearing when pulling the laces tight.

Just above the laces are one of Band of Outsider’s classic designs – the exterior tag label. Normally printed on the inside of the tongue, this shoe features size, model number, materials, and country of origin on the exterior. Of all the special parts of the shoe this is probably the part I like the least. I’ve actually considered taking some acetone to the shoe to remove it. This feature draws a ton of attention to that part of the shoe. It’s just too much for a shoe you’d normally wear with khaki pants or shorts.

Sperry Band of Outsiders Label
Exterior Label

As the shoe lacks laces to keep it tight, the tongue is connected to the rest of the shoe with two green elastic straps. These have held up really well, showing almost no sign of wear.

Another change is that, because the shoe has no real shoe laces, it also lacks the lace running around the throat of the shoe most Sperry A/O’s have. This change makes the shoe much sleeker in design. Unfortunately, this is a major clash with that exterior label, and together they just don’t work.

On the exterior of the back there is just classic Sperry design with the moccasin stitching. This does show a bit of wear and fraying due to the age of the shoe, but nothing to be too concerned about. Inside the heel, however, the white and blue striped panel helps make the shoe feel a bit special.


Rounding out the interior of the shoe, the insole is a ¾ length black fake-leather panel that let’s you know it’s a collaboration, and the rest is a muslin-type lining. Neither of these have held up well. The insole started to peel within the few few wears, and the white lining looked pretty gross almost immediately.

Finishing out the shoe, the bottom is a classic Sperry outsole in off-white.

Sperry Band of Outsiders Shoe
Interior Label

Fit & Comfort:

The Sperry x Band of Outsiders A/Os fit a bit tighter than most other Sperry top siders. While that normally wouldn’t be much of an issue, these also hardly stretch at all. Compared to the Gold Cups I purchased around the same time, you can see that these still feature the same shape they were brand new, while the Gold Cups have completely stretched out. The tight size and the lack of stretchability combined means that you’ll probably want to size up at least a half size. Possibly even a full size if Sperrys are not typically a 1 to 1 of your foot shape.

A Size Comparison of All the Reviewed Shoes Can Be Found Here

Ignoring the sizing issue, these shoes are fairly standard for a Sperry. That means the only thing between you and the ground is a very thin piece of (fake) leather, a thin open cell pad, and the rubber outsole. This is fine for kicking around a bit, the rubber does provide a bit of impact protection, but they don’t have support if you’re planning on going a long distance.

Sperry x Band of Outsiders


The materials on this Sperry x Band of Outsiders topsider are a major let down. While there may be some cheap bonded leather somewhere in the mix, everything you can see and feel on the upper is incredibly cheap feeling plastic. The only redeeming feature is that it’s very resilient, showing almost no creasing. Other than that, it feels terrible, it doesn’t conform to your foot, and all of the edges sharp to the touch. It also causes some really ugly puckering along the toe and back stitching due to the stiffness of the material.

This is especially annoying because it isn’t like Sperry has any trouble getting dark brown leather. Even pulling the normal leather off of their brown A/O would have resulted in a much nicer shoe. With these costing as much as Gold Cups, it’s an insult to their customers.

This cheap exterior leather is also what requires the cloth lined interior. It needs the backing like an Ikea couch. Unfortunately, that cloth interior is as much a let down as the exterior. The lining is incredibly thin. Mine ripped along the toe-box stitching within the first few wears on one shoe, and around wear 20 on the other. The insole Sperry put on top was probably glued on with Post-It Note adhesive. It started peeling almost immediately and hasn’t stopped since.

The outsole is slightly more forgivable, it’s the same outsole that you find on a typical A/O, but even here it’s hard to forgive them. This shoe costs substantially more than a regular A/O, even more than a gold cup. There is no reason Sperry could not have used the softer Gold Cup sole. Even Michael Jordan only makes around $20 per pair to use his name on Jordans. I can’t image Sperry was paying Band of Outsiders five times that.

At least this sole is longer wearing.


The only material on the shoe that isn’t a problem is the leather on the laces. Sperry uses real raw-hide for all of their laces, this included, and it has aged well. That being said, that isn’t enough to overcome the rest. This is, bar none, the worst quality materials of any shoe I own, including sneakers that cost $25.

Sperry Band of Outsiders Review
Outsole – Very Minimal Wear for 100 Wears

Ease of Care:

If there is one saving grace for the upper material they used, it is incredibly easy to take care of. Essentially a piece of plastic, dirt hardly sticks to it and, if it does, wiping it down will take care of it. I’ve never encountered a scenario where I had to use soap, water always does the trick.

There is no point in using conditioner on it. The upper wouldn’t absorb it anyway.

The inside of the shoe is a different story. They get very gross. Very quickly. Designed to be worn without socks, it’s no surprise a white lining doesn’t stay clean. Unfortunately, since the material is so thin, it’s impossible to try and clean it without ripping it. This is something you’ll just need to live with.

Sperry Band of Outsiders Tassel
Green Raw Hide Tassel Loafers


Originally priced at $150, these shoes were among the most expensive Sperrys ever released when they first dropped. This put them well above the Gold Cups (though, these now do go a bit higher in 2020). This was almost what Quoddy charged at the time.


Trying to find these now is almost impossible at any price. Every few months a pair will pop up on eBay, though there were no recent listings at the time of writing. Pricing is all over the board, ranging from $20 to $130 depending on if a buyer is out there or not.

Comparisons are pretty worthless. If you’re looking for this shoe, you’re probably looking specifically for this shoe. Yuketen had made a similar looking shoe, though that was released more than a decade ago. Oak Street Bootmakers had a moc-toe tassel loafer ($348), but it seems like they are clearing out stock of it now and not replacing it.

Otherwise, you’ll need to go with a generic Kiltie to get something close. Prices on these are all over the board. These are not really the same style though.

Sperry Band of Outsiders Toe
Note the Puckering and Sharp Edges on the Toe


If you’re someone who likes the old Band of Outsiders or Scott Sternberg’s design, which I do, these represent a fairly affordable way to get that. As long as you’re aware that the money is going towards the design, they could be a good pick up.

On the other hand, if you’re just looking for a pair of Sperrys that look a bit different, it’s hard to argue these are the best choice. The materials are some of the worst Sperry has ever put on a pair of shoes. That’s only made worse as these were initially priced as one of the highest in Sperry’s history.


Of course, since these shoes can’t be found new anymore, all of this is very dependent on what you pay for them. If there is a great eBay deal out there, it could be a wonderful pick up. Just be sure to know what you’re getting into.

Sperry Band of Outsiders
No Stretching at All

Wrap Up:

For the most part, I love the style of the Sperry x Band of Outsiders shoes. The combination of the classic A/O design, the slight GtH vibe of the tassels, it’s a great combination. I actually ordered this pair from a brick-and-mortar store on the other side of the country.

Unfortunately, the materials Sperry used wouldn’t be OK on a Stacy Adams square-toed shoe. As the dates in this review make clear, I hardly ever wear them. Just over 100 times in five years. When there are other choices available, I just hardly ever find myself reaching for these. They stay on the rack 99% of the time.

Maybe that isn’t a bad thing. The styling is great. These shoes are better on a shelf or a computer screen than on your feet. Time for them to head back.