The Chukka

I bought a 10.5 Chukka boot, and I’m very happy with my purchase. I got them to wear with dress clothes at work. They’re great with slacks, dress pants, or jeans. They have a classic look that works well with dress clothes, but not so flashy that they stand out too much with jeans. The non-slip sole is great on any surface that I’ve walked on, so far. The insole is extremely comfortable! Once they’re broken in, it feels like wearing a shoe that gives your ankle a friendly little hug. My feet are a little bit wide, so I used a boot stretcher that I got from Amazon, and it worked perfectly. I’m retired military, so I wore boots almost every day for 20 years. Very different function and purpose than combat boots, but these Chukkas are the most comfortable boots I’ve ever owned. Give them a couple of days to break in, and use a boot stretcher if any spots don’t fit quite perfectly. It worked great for me, and my feet are happy.

The only thing I would suggest is a different lace. I feel like a 5 year old with my boots coming untied a few times a day. But, that’s an easy $2 fix on my end. I do leatherwork as a hobby, so I’m going to make some zipper inserts that lace in. It might be a cool thing for amberjack to sell those as an accessory.

These are the perfect casual shoes.

This is my 3rd Amberjack boot with the first 2 being the Chelsea (in black and brown) which I mainly wear with work attire. The Chukka is more casual but still pairs well with business casual. Comfortable, sharp looking and well made, I can can see these being my go to footwear when heading to NYC or Boston for a fun weekend.

First off, order a half size larger, because these seem to be rather narrow…that solves the problem. Other than that, it’s a good shoe, but on the pricey side.

These shoes are great…especially if you’re a hobbit who doesn’t need shoelaces longer than a dental floss sample. I’m a size 13, which apparently qualifies me for the “two inches too short” shoelace club. For $200+, maybe toss in enough lace to actually tie the shoe instead of reenacting Fifty Shades of Struggle.

At 6’1”, 200 pounds, I’m thin and long — basically Gumby in leather. And speaking of leather, the design is solid: not too trendy, not too retro, which is another way of saying I won’t look like I shop exclusively at midlife-crisis outlets. The soles? More classic than those “edgy” clown-ish alternatives you see. And yes, Amberjacks are cushier than traditional leather soles, but the consistency of the leather color of chestnut… come on. I’d prefer the darker chestnut, but apparently “rich brown” is reserved for bourbon, not boots.

Although The Original's chestnut color was more fitting, I'm returning them; the chukkas were close enough.

Now, the return process? It was like being trapped in a bad Netflix series — stuck in an endless loop, screaming “I said RETURN, not EXCHANGE!” Support finally bailed me out on a Saturday, so props for that. Customer service works weekends — who knew?

Bottom line: these lighter chukkas aren’t “banana-yellow light,” so with some dark brown polish, I can fake my way into class. Despite the shoelace debacle, I’ll probably buy again — because nothing says loyalty like mild masochism.