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👞 Step up your style and comfort game with Rockport’s Classic Break Chukka!
Rockport Men's Classic Break Chukka Boots combine premium leather craftsmanship with advanced truTECH cushioning and removable memory foam insoles, delivering customizable comfort and reliable traction. Available in extended sizes and widths, these ankle-high boots offer essential arch support and a versatile style perfect for work-to-weekend wear.






| ASIN | B01AB8JPQK |
| ASIN | B0CMJ6DX74 |
| Best Sellers Rank | #116,041 in Clothing, Shoes & Jewelry ( See Top 100 in Clothing, Shoes & Jewelry ) #28 in Men's Chukka Boots |
| Boot Form Type | Chukka |
| Boot Shaft Height | 4.5 Inches |
| Brand | Rockport |
| Closure Type | Lace-Up |
| Color | Dark Brown Leather |
| Customer Reviews | 4.3 4.3 out of 5 stars (2,279) |
| Date First Available | November 3, 2023 |
| Department | mens |
| Embellishment Feature | Zipper, cap toe |
| Global Trade Identification Number | 00889137219154 |
| Heel Type | Stacked Heel |
| Insole Material | Synthetic |
| Item Weight | 18.56 Ounces |
| Manufacturer | Rockport |
| Manufacturer | Rockport |
| Material Fabric | Leather |
| Model Name | Classic Break Chukka |
| Occasion | Evening |
| Outer Material | Leather |
| Pattern | Solid |
| Seasons | Spring/Summer |
| Shaft Circumference | 11 inches |
| Shoe Height Map | Ankle-High |
| Sole Material | Thermoplastic Elastomers |
| Style Name | Classic Break Chukka |
| Style Number | CLASSIC BREAK CHUKKA |
| Toe Style | Closed Toe |
| UPC | 889137219154 |
| Water Resistance Level | Not Water Resistant |
| lining-description | Fabric |
E**E
Very comfortable and great value!!
Good looking boots, very comfortable, and my orthotics fit perfectly!! The size runs a bit large, but after wearing them 5 days in a row, I actually like the added spaciousness. Exceptional value since I got these on sale for 64.
D**L
Comfortable and fit great!
Comfortable and it great! I bought these hoping the size 16 would be a good fit. Love them. Comfortable like sneakers.
Q**.
Nice Looking, OK Comfortable Chukkas
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.
C**R
“Sole Mates – So Good I Bought Them Twice!”
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.
R**E
Excellent product, well priced, and shipped quickly
Excellent product, well priced, and shipped quickly
J**S
Run EXTREMELY LARGE
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.
G**A
Most comfortable “Chukka” out there
Most comfortable boot I’ve ever worn. Stylish but rugged; You can wear these things all day and go from work to a casual night out and they are great.
A**R
Good product
Nice and very comfortable. have been using for the last month - with great satisfaction
I**Z
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.
E**N
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.
S**E
Excellent and as described
T**Q
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.
P**.
So comfortable, i like it
Trustpilot
2 weeks ago
1 month ago