Oak Street Bootmakers Wingtip: The Chonk
Price: $496
Why Buy?
The Oak Street Bootmakers Wingtip is a well made, extremely comfortable, option for any environment where a wingtip works.
Why Avoid?
The Oak Street Bootmakers Wingtip is designed for guys with a lot of volume in your feet, without it, the shoe won’t work.
Specs
| Model | Wingtip |
| Height | 2.7 inch |
| Materials | Chomexcel / Leather |
| Size | 12 D |
| Weight | 743 g / 1 lb 10.2 oz |
| Construction | Goodyear Welt |
| Country of Origin | United States |
History
Oak Street Bootmakers is a brand that is, of course, known for their boots. It’s right in the name. And, despite not being in the name, they are also consistently listed as one of the “big three” in the Maine handsewn world. However, while they have been making those for as long as they’ve been around, they’ve also been making more substantial, goodyear welted shoes. That includes this – one of the first they launched – the Oak Street Bootmakers Wingtip.
Made alongside their boots in the New York State factory they use for production, the Wingtip has actually gone on a bit of an evolution. Originally launched with colors that were more jeans and a t-shirt than formalwear, over time it has “grown up” and now 2 out of the 3 colorways would be perfectly at home with tailored wool outfits. Unfortunately for Oak Street Bootmakers, they launched just in time to meet a world-wide pandemic where everyone worked from home. Ouch.
However, now that we are going back into the office and maybe putting away the casual shoes for a bit, should you consider the Oak Street Bootmakers Wingtip? Or, is this brand something that is strictly for weekend wear? Let’s find out.
Looks
Upper
The Upper of the Oak Street Bootmakers is made up of entirely brown Horween Chromexcel. No complaints from me here, the click seems great – no easy task for this leather – and subtle burnishing adds a bit of differentiation from the army of brown Chromexcel that is the market these days.
Of course, being a wingtip, these have quite a lot of broguing throughout. If you’re not aware, broguing is the little circles cut into the leather. The holes are nice and even, and each is completely cut. I should note, though, in almost every single location of the shoe, the holes are along one side of the stitching rather than the middle. This is clearly intentional, and it’s grown on me over time, but I do wonder what they would look like centered.
The medallion at the toe is a really appealing shape. More western wear than West London, it helps the shoe from being too formal. The rest of the shoe is classic short wingtip. It’s an inoffensive workhorse style that has been around for more than a century and will be around for another century. At least.
Inside, the shoe is line in the classic tan kip lining you see in their boots. My pair did have a few really long loose threads – nearly 2 inches in one case – but that is easy enough to fix. Below your foot, the shoe features Oak Street Bootmaker’s thick veg-tanned insole.
Mid- and Outsole
On the other half of the shoe, the Oak Street Bootmaker has a classic double leather outsole. Nice and thick, it does a good job of playing off the more casual aspects of the upper. The outsole is held on by a 360-degree storm welt, dyed in a matching brown to the outsole. Stitching here is nice and even, and the welt joint is pretty good for a storm welt – which is always harder to get perfect.
One feature that I actually like but could turn some others off is the thickness of the dye on the outsole. It’s really caked on there. I find that it ends up giving the bottom of the shoe some definition, but it is definitely not the standard look.
Flipping the shoe over, the leather outsole’s is a fairly plain design. The only embellishment is a dark brown coating, which was substantially chipped on the edges. Under shoe design isn’t the biggest deal in the world – it will wear off the first time you walk on concrete after all. That being said, Oak Street Bootmaker’s handsewns, admittedly made in a different factory, carry substantial decoration.
Summary
The Oak Street Bootmakers wingtip does exactly what it set out to do – be a slightly casual take on a classic design. The soft look of the chromexcel, the thick outsole, and the medallion work together to hit that look that OSB was aiming for.
While I imagine most people who own these will also own something from their more casual lines – either handsewns or boots – that will do casual better, these can pull that duty. More importantly, these also work just fine with wool trousers and a sport coat. That’s where the flexibility comes in.
There are a couple decisions I don’t personally agree with – centering the broguing would go a long way – but no deal breakers.
Fit & Comfort
Fit
Built on Oak Street Bootmaker’s “Lakeshore” Last, the wingtip is designed to err more on the formal side of design. However, while that often means toe crushing discomfort, I didn’t find that to be the case.
While nowhere near as good as their Elston last – which is my favorite last of any maker – the wingtip is a reasonably accommodating fit. Slightly wide overall, it will comfortably take a lot of different types of feet in length and width.
Unfortunately, it is too accommodating in height. While I’ll admit that I don’t have the highest volume feet in the world, this last offers way too much volume vertically. In fact, the only way I can get any lock-down in these is to do straight lacing and slightly overlap the quarters. And that is before the inevitable stretching from chromexcel.
This space is a real shame, because the shoe fits really well everywhere else. Going down a size would mean a poor fit. I would love to see these with shorter quarters to give a bit more leeway here.
I bought these in a size 12. My feet measure 11.75D on the brannock, and prefer a slightly looser fit. For comparison, I wear a 12 in Alden’s Trubalance and Barrie Lasts. An 11.5 E in Vibergs. And a 13 in most Nike sneakers. For a full list of sizing for all shoes reviewed on this site, click here.
Comfort
Other than the aforementioned fit issues, these wingtips are an incredibly comfortable piece of footwear. The soft leather on the uppers combined with the thick insole and double thickness outsole mean these might just be the most comfortable “dress shoe” I’ve ever tried.
Even better, you’re not sacrificing support either. The arch support is great, and the heel cap does a wonderful job of keeping your foot in place.
Honestly, assuming your foot shape fits the last, I would have no hesitation wearing these on a long day of travel going miles on concrete and up and down flights of stairs. They really are that good.
Materials & Construction
Materials
As I mentioned in previous reviews, one thing I really like about Oak Street Bootmakers is just how transparent they are about their materials. (It certainly makes this section easier to write!)
The upper of the Oak Street Bootmakers wingtip is entirely leather, with Horween Chromexcel backed by calfskin lining. Additional structure is minimal with only soft reinforcement along the heel cap, toe, and eyelets.
Underfoot, Oak Street used their thick veg-tanned leather insole. The one OSB uses is one of the best in the business. It’s supportive, takes your foot’s shape, and is comfortable. There is really nothing to complain about with this.
Moving further down, a cork midsole hides a fiberglass shank – big thumbs up from me. These are definitely metal detector friendly. Finally, a double-thickness leather outsole with a dove-tailed heel finish off the package.
Overall, the materials on the Oak Street Bootmakers wingtip are top notch. There really isn’t anything I would change if I designed it myself.
Construction
The Oak Street Bootmakers wingtip is made with a classic 360-degree goodyear welt. If you want a more in-depth article on what that means, click here. If you want the short version, a piece of leather (known as a welt) is attached to the upper of a shoe. The welt is then sewn onto the outsole.
Goodyear welting is generally considered the best all around option by most, and is great for a shoe like this. The benefits include resoleability, support, and water resistance. The drawbacks include a higher price and longer break in time.
Ease of Care
The Oak Street Bootmaker wingtip’s upper is entirely chromexcel, so you’ll want to follow standard care for that leather.
For conditioning, chromexcel makes it easy. Since the leather is naturally oily, it needs a condition any time it feels dry. For most people, that will be around 2 to 3 times per year – though it could be more (or less) depending on how you wear them. Horween themselves recommend Venetian Shoe Cream, though I find that Bick 4 does just as good a job and costs less.
You can polish this leather, but I find that polish on chromexcel never looks right. Instead, just give it a good brushing with a horsehair brush every few wears. This will pull up the natural oils already in the leather and give it a healthy sheen.
Finally, you’ll want to make sure you use shoe trees. Oak Street offers their own made-in-the U.S. option, or you can get a more affordable pair on Amazon.
When it comes time to replace the outsole, Oak Street Bootmakers offers a recrafting service for a fairly reasonable $120. This is less than any of their competitors for a goodyear welt, and is likely to beat out your local cobbler. That being said, if you prefer your local guy, he should be able to work on these as well.
Pricing & Value
Pricing
The Oak Street Bootmakers wingtip comes in at an MSRP of $496. That MSRP puts them in some pretty competitive territory. Carmina is a dollar less, and Alden isn’t that far off.
Thankfully, it’s fairly easy to find them on sale. In fact, at time of writing they are a full 30% off, or $347. This price point is much more appealing. The only competition here is Grant Stone’s longwing for $318. While I’m a fan of Grant Stone, paying only a $30 premium for U.S. construction will likely be seen as a fair trade off for many.
Value
As you can probably guess, the value of the Oak Street Bootmakers wingtip will depend on if you pick them up on sale or not.
Even at full price, I think you’ll be happy with the purchase. While not quite as finely made as something like the Carmina, U.S. labor and materials cost more than their European equivalent, so it isn’t like OSB is simply pocketing the difference.
On sale, though, these are extremely appealing for the price. You can’t find the combination of U.S.-made, high-quality materials, and comfort anywhere else.
Wrap Up
The Oak Street Bootmakers wingtip was so close to being the perfect workhorse dress shoe. The one you wear several times a week, feel comfortable throwing in a suitcase for a work trip, etc. The durable build and high-quality materials are just begging to be worn in.
Unfortunately, the combination of long quarters and a high volume last means that for a lot of guys, they simply just won’t fit. And, if your shoe doesn’t fit, none of that other stuff matters.
If you have a high-volume foot – stop reading here. You’ve gotten this far, so you’re clearly interested. Just buy them. You won’t regret it. If you don’t have a high-volume foot, well… you can join me being jealous of the other guys enjoying their Oak Street Bootmakers wingtips.