Search  for anything...
Rockport

Rockport Men's Classic Break Chukka Boots

  • Based on 2,316 reviews
Condition: New
Checking for the best price...
$73.98 Why this price?
Save $75.96 was $149.94

Buy Now, Pay Later

As low as $12.33 / mo
  • – 6-month term
  • – No impact on credit to apply
  • – 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, Affirm, Afterpay, Apple Pay, and PayTomorrow. 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

FREE 30-day refund/replacement

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: In Stock.
Fulfilled by Amazon
Arrives Monday, Jun 22
Order within 21 hours and 23 minutes
Available payment plans shown during checkout
Protection Plan Protect Your Purchase
Checking for protection plans...

Size: 10


Color: Dark Brown Leather


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.

Department ‏ : ‎ mens


Date First Available ‏ : ‎ November 3, 2023


Manufacturer ‏ : ‎ Rockport


Manufacturer’s warranty can be requested from customer service. Click here to make a request to customer service.:


Best Sellers Rank: #62,438 in Clothing, Shoes & Jewelry (See Top 100 in Clothing, Shoes & Jewelry) #8 in Men's Chukka Boots


#8 in Men's Chukka Boots:


Customer Reviews: 4.3 4.3 out of 5 stars (2,317)


Color: Dark Brown Leather


Toe Style: Closed Toe


Boot Form Type: Chukka


Heel Type: Stacked Heel


Seasons: Spring/Summer


Pattern: Solid


Style Name: Classic Break Chukka


Occasion: Evening


Boot Shaft Height: 4.5 Inches


Item Weight: 18.56 Ounces


Shoe Height Map: Ankle-High


lining-description: Fabric


Outer Material: Leather


Insole Material: Synthetic


Sole Material: Thermoplastic Elastomers


Material Fabric: Leather


Brand: Rockport


Model Name: Classic Break Chukka


Style Number: CLASSIC BREAK CHUKKA


UPC: 889137219048


Global Trade Identification Number: 48


Manufacturer: Rockport


Closure Type: Lace-Up


Water Resistance Level: Not Water Resistant


Frequently asked questions

If you place your order now, the estimated arrival date for this product is: Monday, Jun 22

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.

Similar Products

Top Amazon Reviews

    • Great boot!
Size: 10 Color: Dark Brown Leather
Fit as expected, comfortable and look good both casually and with a suit.
Reviewed in the United States on May 13, 2026 by Gordon Gray
    • COMFORTABLE!!!
Size: 6.5 Wide Color: Dark Brown Leather
Look great (I am asked what are those? Where’d you get those?). Feel even better; solid but light, wide enough toe box, nice angle heels to toe. I might get another pair…
Reviewed in the United States on May 29, 2026 by Marian DiCicco
    • Looks sharp, size is wider than expected, nice casual shoe
I picked up a pair of these boots in the "Dark Bitter Chocolate Suede" (which sounds like a bad name for a band now that I type it out) size 13 wide. And they are wider, almost too wide. I can tell that a size 12 would not work and past experience with 13 regular sized shoes has typically not worked out long term. The boots looks sharp and feel pretty good. Arch support is not superb so I augment it with a pair of inserts for more cushioning and support. They are appropriate for work, social events, and dry weather outings. But I do not wear them on rainy days. The build quality seems OK, not quit high-end but like these should last several years with routine normal use. The dark chocolate color matches well with jeans or cords and the understated looks do not call undue attention to my size 13 feet. ... show more
Reviewed in the United States on January 2, 2020 by loce_the_wizard
    • 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
    • Very comfortable and great value!!
Size: 10.5 Color: Dark Brown Leather
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.
Reviewed in the United States on March 16, 2026 by EE
    • Good shoe for the low price
Size: 9.5 Wide Color: Dark Brown Leather
They are ok for the price but I bought the Florsheim chukkas instead … better quality and fit
Reviewed in the United States on April 21, 2026 by Paul Fishburn
    • “Sole Mates – So Good I Bought Them Twice!”
Size: 10 Wide Color: Dark Brown Leather
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. ... show more
Reviewed in the United States on July 13, 2025 by Clarence “Tuck” Tucker
    • Used boot
Size: 10 Wide Color: Dark Brown Leather
The left boot had a noticeable scratch on leather. Nice boots but obviously a return. Amazon and vendors are getting shady
Reviewed in the United States on March 25, 2026 by guy

Can't find a product?

Find it on Amazon first, then paste the link below.
Checking for best price...