Rockport Men's Classic Break Chukka Boots

I don’t usually write reviews, but these Rockport Chukka Boots absolutely deserve one. I liked them so much, I bought a second pair after I literally wore the soles off the first — and even wore through the liner. That’s how often I wore them. As a larger guy, finding boots that look sharp and don’t cause foot pain can be a challenge. These nailed it. The cushioning is fantastic, the fit is supportive without being tight, and I could wear them all day without aches or hotspots. Whether I was at work or out for the evening, they held up and looked great doing it. They strike that perfect balance between fashionable and functional — clean enough to dress up, but still casual enough for everyday wear. I’ve gotten compliments, and more importantly, I’ve gotten serious mileage out of them. If you want something comfortable, stylish, and built for real use, these Rockport chukkas are 100% worth it. I’ll probably buy a third pair when the time comes.

Comfortable and it great! I bought these hoping the size 16 would be a good fit. Love them. Comfortable like sneakers.

I'd prefer to spend more for high quality boots, but I was looking to save some money and liked the look of these Rockports, and Rockports are generally comfortable. I've had my dark brown pair for a few months now and have worn them maybe 15 times. They look more worn in now, but not more beat up than I would expect after 15 wearings. As you can see in my pictures, the coloring isn't quite dark brown, but more of a standard brown. My pictures' coloring is not far off from what they look like in real life. I'm pretty particular with how my shoes look and this pair's profile is really nice. From the side they're not clunky, and the width is just right. The heel is about 3/4" high. For me the drawback with these shoes is the comfort. They're a little firmer than I expected of Rockports. They're not going to beat up your feet, but if I stand in them too long my feet will ache a bit (disclaimer: I don't have much body fat so my feet lack that extra cushioning.). I typically wear a 9.5 with sneakers and other shoes, but I fit a 9 with Rockport. Overall I do like these chukkas and they're worth it at their price point.

The boots will make a great accessory to your wardrobe. Please consider that the boots are not a snow, winter or rain boots. The boots are a true dress causal style item. You may need to add a separate pair of waterproof dress or dress causal boots or snow boots to your wardrobe if you live in a cold or rainy climate. The boots are rather ruggedly built, but they are not clunky. They may feel a little stiff during your first two wearing, but they will soon loosen-up and begin to feel more and more comfortable. The boots will look quite stylist with a pair of jeans or with a pair of very nice dress slacks. The boots has the appearance of a much more expensive pair. Please purchase a neutral color shoe shine sponge or a sponge the color of the boots in order to keep your boots looking their maximum best. The only issue I have with the boots is that they often come untied due to the apparent waxing on the laces; however, inexpensive replacement laces from Amazon or your local store will take care of that.

This is the third pair of these boots I have had over the last 9-10 years. They look great. Soft leather. Comfortable, but I recommend an upgraded insole. The only downside is these are chocolate brown and I thought they'd be close to the same color as my previous pairs which is sort of an English Tan.

These Rockport shoes look and feel pretty good. However, they run HUGE. I normally wear a 11.5 - 12w and I've needed to order and send these back twice now. The 11.5s were enormous and now the 11s are still really large. I compared the overall size of the 11s with another chukka boot I've been wearing which is a 12. Overall they were the same size. I guess for these to fit I need to order a 10.5?! Since I've ordered and returned twice, I'm just not going to bother and go with something else. I used to wear Rockport nonstop but now I can't ever seem to get the right size.

**Update** Wore these on a recent trip to Paris. Walked over 50 miles over the course of a week including many, many flights of stairs. These shoes held up perfectly and my feet felt fine. These get my highest recommendation. I can't recall a shoe I've owned that would shrug off such punishment. Bought these to have some comfortable shoes that put up with a lot of walking, look nice and definitely aren't sneakers. It checks all of those boxes. These may be the most comfortable shoes I've worn. I wear them several times a week and do a ton of walking in them, and my feet feel absolutely fine. I usually wear 11.5, but I ordered these in 11 wide based on Amazon's recommendation. Kudos to Amazon for getting that right. In addition, I've received several compliments on how nice they look. This is a really nice shoe. I definitely recommend them if this is a style you're looking for.

Nice and very comfortable. have been using for the last month - with great satisfaction

La calidad es muy buena son muy cómodas valen la pena, solo que vienen grandes como medio número pedí 26cm creo que el 25.5 me hubiera quedado perfecto pero me gustaron mucho me las quedaré.

Es un calzado sumamente cómodo, fresco y de un aspecto agradable, francamente nunca había adquirido esta marca de zapatos, pero este calzado no defrauda en absoluto, es amplio, por lo que sugiero adquirir tu talla exacta a menos que te agraden los zapatos amplios. Me fue tan bien con esta adquisición que compre otro modelo de la misma marca, ahora de mi talla, y estoy muy agradecido porque la comodidad es increíble.

Excellent and as described

Nice boots , slightly lighter in shade , would have preferred a perfect tan. Otherwise quite comfortable & the leather is soft . Looks great on demin or cargoes. Fit to size.

So comfortable, i like it