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Oak Street’s Limited Lakeshore Boasts 3 Sneaky Comfort Hacks

William Barton

Boots, Leather, Heritage Fashion, Denim, Workwear

William founded BootSpy in 2020 with a simple mission: test and review popular men’s boots and give a real, honest opinion. Since then, we've welcomed over 5 million readers on our boot reviews and boot care guides. Reach out to him for your own personalized boot recommendation at william@bootspy.com. Or join 50,000+ subscribers on the BootSpy YouTube channel, or send him a message on the BootSpy Instagram. Read full bio.

Last Updated: Mar 20, 2024
3 min read

Oak Street Bootmakers just launched a limited edition version of their Lakeshore Boot that’s basically a masterclass in boot comfort.

If I’m honest, it’s not a style I’d wear personally. But, I felt the way it’s made offers some insights into boot construction and why some brands feel better on your feet than others.

Oak Street Lakeshore

I’ll share with you the three sneaky comfort tricks Oak Street is using to make this limited edition Lakeshore an ideal springtime service boot.

1. Hand Lasting

In the world of high quality boots, there’s two ways of “lasting” a boot. A last is the plastic or wooden form around which the leather is stretched. The shape of the last determines the shape of the boot.

Here’s a quick 60-second video on what a boot last looks like if you’re interested.

Back in the day, leather was stretched around the last with a pair of “lasting plyers.” This handmade process required the craftsman to understand the piece of leather he was working with—stretch too far on one piece and the leather might tear.

Since every piece of leather is different, craftsmen with thousands of working hours under their belts could instinctively understand where the hide was tense or too loose.

Oak Street Lakeshore profile both boots

A lot of this lasting process moved to machinery, where a machine grabs the leather and pulls it down over the last, and then cinches it at the bottom.

Both methods create high quality boots.

But Oak Street Bootmakers, while originally pushing toward more mechanized production methods, have put much more focus recently on their hand-lasting program. And the reason is simple: hand-lasted boots just fit and feel slightly better. Each part of the upper is perfectly tense.

That can lead to an easier break in and less “shape changing” or slouching as the boot ages.

Some hardcore folks only get handlasted boots. I’m not that particular, but I do think hand-lasting boots is admirable and the craftsmen look cool while doing it.

2. Vibram 2060 Wedge Sole

Oak Street Lakeshore sole

Wedge soles are just objectively more comfortable than heeled soles.

You get more even arch support, and typically bootmakers will swap out a leather midsole for a rubber slip sole, which just makes the boot more flexible and lightweight overall.

While this limited edition Lakeshore still has that leather midsole, the Vibram 2060 wedge is a lot nicer than the popular Vibram Christy wedge, in my opinion.

I tried the Vibram 2060 on the Nicks Moc Toe and found it to be more shock absorbent—and most importantly, more durable.

Author William Barton wearing Nicks Moc Toe Boots
I’m wearing the Nicks Moc Toe here, but it has the same Vibram 2060 wedge sole. Which I can attest—it’s comfortable.

Decked with this wedge sole, OSB’s new Lakeshore is all set for springtime strolls.

3. Badalassi Carlo Nemesi Leather

Oak Street Lakeshore leather detail

Badalassi Carlo is an Italian tannery with a rich history that’s been gaining a lot of attention from the boot world in the past few years.

And their Nemesi leather is an aniline Vachetta leather.

Vachetta is what Louis Vuitton uses to line their bags. It’s dat fancy stuff.

If you’re into sushi, it’s the equivalent of tuna belly.

It’s a fattier type of leather, so it’s soft, supple, and smooth.

While this particular Nemesi leather is only lightly milled, so it stays a bit more firm, it’s still rich and flexible in its core.

Get this Limited Edition Lakeshore Boot

Oak Street Bootmakers Lakeshore - Badalassi Nemesi

Hand-lasted, wedge-soled, Vachetta-leathered service boot goodness. Limited edition only.

Check Price

I should also mention that the Lakeshore model offers a little more room in the toes, which also helps with comfort. I could’ve added that, but as a writer I like the sound of “three tricks” better than “four tricks.”

These puppies are only available until this batch is up. Knowing Oak Street, it won’t take long before they’re gone for good.

I reviewed the OSB Trench boot a while back. First thing I did was completely soak it in a river. It still lives.


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