Review: Jack Erwin “Chester” boots

Recommending shoes to people is tough, especially in ready-to-wear brands. You can make reasonably informed decisions based on price, basic quality construction standards and your own aesthetic point of view. But shoes are the kind of clothing item where it either fits or it doesn’t – and almost nothing can be done to the shoe if you find it doesn’t work for you. 

And with the rise of several direct-to-consumer brands in footwear online, it’s tougher still for you to know just how well something will fit you – let alone how it’ll feel after a full month or more of wearing. Carefully walking on carpeting at your home or office and trying not to crease the front of the toe box isn’t the same as putting some miles on a shoe. 

There’s a lot I liked about these Jack Erwin boots, their “Chester”model. The material was on par with others in their price tier (or slightly above it) and it ticked off the checkboxes for a decent build (Goodyear welting) and looks. Heck, it even had the studded rubber sole for a bit more traction in bad weather. 

But the first two weeks were painful to wear these. I learned not to wear regular dress socks and instead thicker casual socks with them. In that time period I only wore them while at work and laced them only halfway up. I used leather conditioner several times and worked the boot with my hands in hopes of softening the leather up. Specifically, the boot dug in rather tough on my interior ankle bones and above my heel several inches where the top of the boot’s edge ended. 

Eventually, the boots were comfortable enough to walk in to grab lunch and later for my full daily commute. Just know that if you’re considering this model boot that the leather around your ankle and shin will take some real work breaking in while wearing decently thick socks. I’ve experienced “break-in periods” before with boots, but not at this level. 

(I will note that in his review at Well Spent, Nick Grant’s break-in only lasted five days – so maybe I’m a wimp on my feet.)

Also, if you have wider feet, you might want to reconsider. I have narrow feet (typically wearing 10.5C or 11B on the Brannock U.S. scale) and found the boots to be a very snug fit. I’m not sure someone with an “E” fitting with thick socks could wear these comfortably. 

Looking up other reviews of Jack Erwin, you’ll see a lot of them back from 2013, but it’s tough to compare these to the shoes from that era. Production of those shoes were done in Portugal, whereas Jack Erwin’s moved manufacturing to Spain. Also, construction varies from by model – using either Blake, Bologna or Goodyear. 

If your budget is around $200, I’d give Jack Erwin a look and use their free shipping and free returns – or if you’re in NYC drop by their showroom. For the price, it’s hard to suggest something else. I have a feeling their shoes won’t require the same dedication to break-in as their boots. But you won’t know until you try them on.