Search  for anything...

Rockport mens Classic Break Chukka

  • Based on 1,577 reviews
Condition: New
Checking for product changes
$99.95 Why this price?
Memorial Day Sale · 29% off was $140.00

Buy Now, Pay Later


As low as $16.66 / mo
  • – 6-month term
  • – No impact on credit
  • – Instant approval decision
  • – Secure and straightforward checkout

Ready to go? Add this product to your cart and select a plan during checkout.

Payment plans are offered through our trusted finance partners Klarna, PayTomorrow, Affirm, Afterpay, Apple Pay, and PayPal. No-credit-needed leasing options through Acima may also be available at checkout.

Learn more about financing & leasing here.

Selected Option

Free shipping on this product

This item is eligible for return within 30 days of receipt

To qualify for a full refund, items must be returned in their original, unused condition. If an item is returned in a used, damaged, or materially different state, you may be granted a partial refund.

To initiate a return, please visit our Returns Center.

View our full returns policy here.


Availability: Only 7 left in stock, order soon!
Fulfilled by Amazon

Arrives Saturday, May 31
Order within 13 hours and 26 seconds
Available payment plans shown during checkout

Size: 12


Color: Dark Brown Leather


Features

  • 100% Leather
  • Imported
  • Rubber sole
  • Shaft measures approximately 4.5" from arch
  • GENUINE LEATHER AND SUEDE: Easy-to-care-for textured materials bring quality and style to a classic men chukka boot
  • ALL-DAY COMFORT FOOTBED: Molded EVA footbed and heel cup provide foot-conforming, flexible, and lightweight impact absorption
  • SOFT LINING: Soft-knitted fabric lining feels great against the foot
  • GRIPPY OUTSOLE: TR outsole provides a durable grip on a variety of surfaces for a steady stride

Description

The Classic Break Chukka has versatile style to get you through the day and into the evening. Premium leather or suede uppers. Lace-up closure. Soft knit fabric linings. EVA footbed and heelcup conforms to the shape of the foot. TPR outsole for grip. Imported. Measurements: Weight: 1 lb 2.6 oz Shaft: 4 1⁄2 in Product measurements were taken using size 9, width M (D). Please note that measurements may vary by size. Weight of footwear is based on a single item, not a pair.


Item model number ‏ : ‎ CLASSIC BREAK CHUKKA


Department ‏ : ‎ mens


Date First Available ‏ : ‎ October 13, 2023


Manufacturer ‏ : ‎ Rockport


Frequently asked questions

If you place your order now, the estimated arrival date for this product is: Saturday, May 31

Yes, absolutely! You may return this product for a full refund within 30 days of receiving it.

To initiate a return, please visit our Returns Center.

View our full returns policy here.

  • Klarna Financing
  • Affirm Pay in 4
  • Affirm Financing
  • Afterpay Financing
  • PayTomorrow Financing
  • Financing through Apple Pay
Leasing options through Acima may also be available during checkout.

Learn more about financing & leasing here.

Top Amazon Reviews


  • They Feel Long
Size: 10.5 Wide Color: Dark Brown Leather
Others have said these size a little large but it's odd how they size large. They feel too long is the easiest way to put it. I ordered 10 1/2 W and these really feel as long a an 11 W. Everything else about the size is perfect. I have a wide foot and my dress shoes usually pinch, but these are great in that aspect. I'm going to order another pair size 10 W and see if they fit better. I'll probably donate the pair that fits less perfect to a local shelter. Like I said, it's otherwise a good shoe, just looks and feels a little too long. ... show more
Reviewed in the United States on September 16, 2023 by Ben M.

  • Excellent boots
Size: 9 Color: Dark Brown Leather
Excellent quality boots! Sizing is spot on. This company always nails it with footwear.
Reviewed in the United States on September 17, 2023 by wirecutter

  • A Great Pair of Dress Causal Ankle Boots...!
Size: 12 Wide Color: Dark Brown Leather
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. ... show more
Reviewed in the United States on May 28, 2023 by FB

  • In hindsight--I'd pay $30
Size: 6.5 Wide Color: Dark Brown Leather
I hadn't been inclined to try Rockport, but I wanted a brown boot--and these were described as 50% off at $60, so I bit. I know TPR, the outsole material, is not one of the more durable sole types, but I'm fine with it--I chose these chukkas for the office, not hiking. What DOES irk me happens whenever I dress the boots up with the world's gold-standard leather conditioner--Saphir: After a few weeks the finish looks odd like the conditioner’s not all absorbed. My half-dozen pairs of dress-leather footwear drink up Saphir like a kid with chocolate milk--except this pair seems to have a touch of reflux. Is it...it is leather, right? These chukkas normally go for $120 ? For real ? Design of these Rockports is nice and they feel great; but for about the same $60, I've had comparable Clarks that NEVER looked like they were molting. Going forward in this price tier, Clarks and Cole Haan for me. ... show more
Reviewed in the United States on May 31, 2023 by Amazon Customer

  • Okay for the (discounted) price; Wide fit could be a bit wider and there's no arch support.
Size: 8.5 Wide Color: Dark Brown Leather
I don't know why, but I've struggled to find wide chukka boots at a reasonable price. I have a very high instep, and go up to EEE in some shoe brands, even with an accommodating last (think Alden's Barrie last for reference.) I saw these clunky round-toe Rockports on sale at Amazon and gave 'em a try. First, the most disappointing thing to me is the brown coloring. In both the official product and customer pictures, there is a notable burnishing in the heel and toe areas. Mine are a solid medium brown, no visible burnishing. I can recreate that with some darker polish over time, but I was hoping these would have that nice burnishing. Mine don't. In the wide size, the toe box is nice and roomy. However, the middle section and instep are a bit snug for me. If you normally wear a single E then you may not have an issue with this; for me and my sometimes-EEE feet, it's a minor issue. I am hopeful they will loosen up a bit as they break in, and assuming this is real leather, they should. There is almost zero arch support, and I don't find the Rockport insoles to be anything special despite their "Trutech" label. Any generic gel insole will be more shock absorbing, and even a modest amount of arch support would be welcome. For the price I paid, I'm probably complaining too much. The overall fit is okay, maybe slightly long as some have noted. But I looked at chukkas twice the price at DSW and Nordie Rack and none were as comfortable as these. Yes they are a bit clunky and I prefer a more elongated toe over the round toe on these, but overall they are a good value. In fact, I like them enough that I am tempted to buy another pair in suede! ... show more
Reviewed in the United States on November 16, 2019 by VA2NC2VA

  • Nice looking shoe did not last long
Size: 11.5 Wide Color: Dark Brown Leather
This shoe offered very little arch support and the width fit loose. not comfortable for an every day dress shoe
Reviewed in the United States on August 6, 2023 by Kevin Jamieson

  • ran small
Size: 14 Color: Dark Brown Leather
Shoe was lacking in arch support .
Reviewed in the United States on August 2, 2023 by starfan716

  • Comfy, Stylish, Casual or Dress Up!! Yay.
Size: 12 Wide Color: Dark Brown Leather
I waited way too long to buy these! They popped up again with a price drop and it was a great reminder. Jumped right on it. Nice support and comfortable like Lockport's but not looking like Sr. walking shoes!! Haha! Worn them casual with jeans and dressed with full suit and tie. Perfect for both. Highly recommend ... show more
Reviewed in the United States on May 22, 2023 by Bobbos

Can't find a product?

Find it on Amazon first, then paste the link below.