As you may be aware by now, I am very much a sneaker guy. So when Jack Erwin approached me about giving their Chester Boots a go, I thought “sure, but you’re already in the hole, so good luck!”



By the sheer looks of them, I was on-board. And they’re marketed as the “work boot for the modern working man,” which I assume is an account supervisor at an ad agency who twilights as a freelance style writer, so that’s right up my alley too. And the construction (handcrafted in Spain), and materials (calf-skin uppers, supple leather lining, Goodyear welted rubber sole, and a cap toe) were all helping to win me over as well.



Plus, I got plenty of unsolicited compliments the first day I wore them, but that could just be because my coworkers are sick of me wearing silly sneakers all the time and were happy for the switch-up. Either way, on first impression, these definitely have the makings of an everyday boot. Boardroom to the, uh, booze-room? I don’t know how that saying goes.



Unfortunately, they weren’t super comfortable right off the bat – they definitely wear as hard as they look. But, my feet are fairly wide, and most of my discomfort was / is along the side of the boot, so that might be why. Also, my feet are probably just used to being pampered by knit uppers and foamy soles. On the upside, the boots have noticeably started to break in with more wear, but it may take a little while longer until they’re all-the-way comfy, considering how infrequently I wear boots casually. At the same time, when I used to wear Trickers boots religiously, everyday was like a test of my pain-threshold, and these aren’t nearly as bad as that.



All-in-all, the Chester Boots are very versatile, and at only $220, give you an incredible bang for your buck if you’re willing to put in the work to break them in. I’m sure there are some tips and tricks I should know that would help me get past the initial discomfort and solve all of my first world problems. Let me know in the comments if you’ve got any.

UPDATE: Today is my fifth day wearing the boots, and I’m feeling zero discomfort, so I think the break-in period may already be over.

For price and purchase info, visit Jack Erwin.