---
product_id: 39773315
title: "Men's Classic Break Chukka Boots"
brand: "rockport"
price: "R5597"
currency: ZAR
in_stock: true
reviews_count: 13
category: "Rockport"
url: https://www.desertcart.co.za/products/39773315-mens-classic-break-chukka-boots
store_origin: ZA
region: South Africa
---

# truTECH shock absorption Memory foam removable insoles Durable traction outsole Men's Classic Break Chukka Boots

**Brand:** rockport
**Price:** R5597
**Availability:** ✅ In Stock

## Summary

> 👞 Step into comfort and style that works as hard as you do

## Quick Answers

- **What is this?** Men's Classic Break Chukka Boots by rockport
- **How much does it cost?** R5597 with free shipping
- **Is it available?** Yes, in stock and ready to ship
- **Where can I buy it?** [www.desertcart.co.za](https://www.desertcart.co.za/products/39773315-mens-classic-break-chukka-boots)

## Best For

- rockport enthusiasts

## Why This Product

- Trusted rockport brand quality
- Free international shipping included
- Worldwide delivery with tracking
- 15-day hassle-free returns

## Key Features

- • **Perfect Fit Range:** Extended sizes and widths for every foot shape
- • **All-Day Cushioning:** truTECH tech absorbs shock for lasting heel comfort
- • **Custom Fit Freedom:** Removable memory foam insoles adapt to your lifestyle
- • **Steady Stride Grip:** Durable outsole ensures traction on diverse surfaces
- • **Arch Support Engineered:** Designed to keep you moving comfortably all day

## Overview

Rockport Men's Classic Break Chukka Boots combine lightweight truTECH cushioning with removable memory foam insoles and a durable traction outsole, delivering all-day comfort and stability. Available in extended sizes and widths, these boots offer essential arch support and a versatile style perfect for work or weekend wear.

## Description

The Collection offers a bevy of mod work-to-weekend profiles that pack enough personality to pair with anything. Featuring stylish washed leathers and burnished suedes, its lightweight, flexible construction has comfort covered with a soft knit lining and cushioning foam foot bed.

Review: “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.
Review: 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.

## Features

- CUSHIONED COMFORT: truTECH Technology is Rockport's lightweight comfort feature that absorbs shock and provides long-lasting cushioning in the heel
- REMOVEABLE INSOLES: Perfect for customizing your fit or accommodating orthotic inserts, these memory foam removable insoles provide ultimate comfort and support, our removable insole shoes adapt to your lifestyle and needs
- STABILITY AND TRACTION: outsole offers long-wearing durability providing a durable grip on a variety of surfaces for a steady stride
- EXTENDED SIZES AND WIDTHS: Discover the perfect fit for every foot with our extended range of sizes and widths
- ARCH SUPPORT: Engineered for essential arch support and comfort, these shoes keep you moving comfortably all day, ideal for anyone on the go, making them perfect for active lifestyles, long workdays, or those needing extra foot care

## Technical Specifications

| Specification | Value |
|---------------|-------|
| ASIN  | B0CMJ6DX74 |
| Best Sellers Rank | #89,585 in Clothing, Shoes & Jewelry ( See Top 100 in Clothing, Shoes & Jewelry ) #30 in Men's Chukka Boots |
| Customer Reviews | 4.2 4.2 out of 5 stars (2,264) |
| Date First Available  | November 3, 2023 |
| Department  | mens |
| Manufacturer  | Rockport |

## Images

![Men's Classic Break Chukka Boots - Image 1](https://m.media-amazon.com/images/I/61T6DTk+LwL.jpg)

## Questions & Answers

**Q: usually 11 w what size should I get**
A: My experience has been to order true to size.

**Q: Hi do these come in 10.5 extra wide?**
A: Not a clue. Ask the Seller.

**Q: Hi do these shoes come  10.5 extra wide?**
A: I'm sure it does, but make sure you really need WIDE because it's TRULY WIDE.

## Customer Reviews

### ⭐⭐⭐⭐⭐ “Sole Mates – So Good I Bought Them Twice!”
*by C***R on July 13, 2025*

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 fit great!
*by D***L on November 27, 2025*

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

### ⭐⭐⭐⭐ Nice Looking, OK Comfortable Chukkas
*by Q***. on December 28, 2018*

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.

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**Shop now:** [https://www.desertcart.co.za/products/39773315-mens-classic-break-chukka-boots](https://www.desertcart.co.za/products/39773315-mens-classic-break-chukka-boots)

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*Product available on Desertcart South Africa*
*Store origin: ZA*
*Last updated: 2026-03-13*