Shoe Dissections

Oak Street Bootmakers: Boat Shoe Dissection

OSB Dissection

I’ve had this shoe for months and have held off on doing the dissection because I really wanted to do it side-by-side with a Sperry to compare the two. But, after a dozen or so trips to my local thrift stores I just couldn’t namage to find a comparable boat shoe from Sperry… but I do happen to own a pair myself. I wear these things all the time, so I (unfortunately) won’t be tearing them down, but I did find it interesting to note its outward similarities with the OSB.

OSB 01

OSB 02

My first thought was that they are nearly identical in construction and even seem to use the same sole. The biggest difference, of course, being that the OSB uses Horween Chromexcel leather compared to Sperry’s less flashy, yet extremely comfortable, no-name cow parts; which is very likely what accounts for the $112 discrepancy in their prices ($262 vs $150).

OSB 03

To my knowledge there isn’t a way of sewing boat shoe/ moc. uppers by machine, so it’s not really not all that noteworthy that both Sperry and OSB advertise these shoes as being hand-sewn… but they are. There’s a pretty significant difference in the size and shape of the knots used to begin/ finish this stitch.

OSB 04

can’t imagine that this has any impact on the quality or durability of the shoe, but it does make a minor stylistic difference. The OSB knot is much chunkier and really draws your attention to it.

OSB 06

I noticed another difference while trying to remove the shoelace from my Sperry; namely, that it did not come out. The OSB (shown above) on the other hand can have its laces removed because they aren’t attached to the lace that runs around the back of the shoe.

OSB 05


Here you can see that the lace on the Sperry continues into the shoe, where it runs around the back to the other side. Personally, I kind of like being able to cinch it up a bit tighter and have that draw up the whole shoe.

OSB 07

I thought that it was a little bit funny that both shoes used a leather half sole insert over a blue half sole cushion

OSB 08

They’re virtually identical other than the fact that the OSB’s arch support is a little bit more pronounced.

OSB 09

Here’s the pursed-together section of the heel that’s so characteristic of boat shoes. The idea is that the whole shoe, other than the tongue/ top, is one big piece of leather that wraps underneath the whole thing and is drawn together around the top. So, in order to keep it from bunching up around the heel when it’s stretched over, that portion has to be slit open so that some material can be removed, and is then sewn back together, resulting in this raised lip-looking stitch along the back.

As you’ll see later, the OSB adds this stitch for cosmetic purposes, whereas it appears to be genuine on the Sperry.

OSB 13

Here’s the insole. I expected to find that it was connected to the bottom of the shoe by a stitch that ran all the way around the insole, but I saw something different. It was connected only in two places: there were 7 or 8 stitches along the right side of the heel and another 7 or 8 along the left side of the arch/ ball area. The whole thing seemed secure enough, but I couldn’t help but wonder how they decided on those two spots in particular.

OSB 14

So, after cutting those stitches…

OSB 15

The insole popped out; this one also only a half sole. The big thing I was looking for here was a shank. I kept thinking that I remembered hearing in an OSB factory tour video recently that their boat shoes were made with shanks, but apparently not; at least not this one. Not that it’s a bad thing, these shoes are supposed to be flexible after all, so I suppose it makes sense.

OSB 16

Next was the very satisfying task of cutting off the top.

OSB 17

With the top removed, you can really see how it’s pretty much supposed to be all one piece of leather. My only guess as to why there’s a hole in the heel is to possibly accommodate a shank in some models and/or to avoid having a stitch directly underneath your heel.

OSB 18

Here’s where the lace that runs around the back is anchored.

OSB 19

I then cut the small stitch that keeps the top folded down and flipped it up. Again, you can really see how this whole shoe could pretty much be made with one big piece, but it’s probably much easier for manufacturing purposes to make the folded-over-bit separately; what with the eyelets and fine stitching on it. Furthermore, if you didn’t use a separate piece here, you’d expose the unfinished flesh side of the leather when you folded it down, which might not look all that great.

OSB 21

…with the folded-over-bit removed.

OSB 22

This is pretty typical on all the shoes I’ve seen: a plastic material sandwiched between two layers of leather around where the eyelets are. It keeps the leather from stretching when you tie them.

OSB 23

Here you can see what I was talking about earlier when I said that the pursed-together heel portion on these was cosmetic. It’s done with a separate piece of leather, which is then sewn onto the heel area over a very standard sig-zag stitch, which holds the two parts of the heel section together.

OSB 24

With all of the upper pieces disassembled, I started to remove the whole upper from the sole.

OSB 25

OSB 26

With the upper removed, I flipped the heel inside out and found this little patch that covers up the zig-zag heel stitch.

OSB 27

OSB 28

And here’s the fully disassembled upper.

OSB 29

…the underside

OSB 30

Overall there weren’t too many surprises but it was still pretty interesting to see how one of these fits together. More than anything, it makes me wonder what the Sperry looks like when it’s taken apart and whether or not the fact that it has a true heel stitch means that it really is made from one big piece of leather.

OSB 31


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