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Men's Classic Break Chukka Boots

Prices as of September 27, 2026, as listed by each retailer — verify the current price on the retailer's site before purchase.

Price history tracked at Macy's price tracker

14-day low
$112.00
Sep 14 · Macy's
Best price
$112.00
−0% vs high
14-day high
$112.00
All stores
$112$112$112
Sep 14Sep 27
  • Macy's
Lowest in 14 days: $112.00 at Macy's. Highest: $112.00. Current best is 0% below the 14-day high.

About this product

Rockport Men's Classic Break Chukka Boots are a versatile footwear option designed for both casual and semi-formal settings. Featuring a premium leather upper with a soft knit lining and cushioned foam footbed, these boots offer lightweight comfort and flexibility. The round toe and lace-up closure provide a secure fit, while the 1.06-inch heel height adds subtle elevation. Ideal for pairing with jeans or a jacket and tie, they combine style and functionality in a modern work-to-weekend silhouette.

  • premium leather upper
  • cushioned foam footbed
  • lightweight and flexible
  • lace-up closure
  • spot clean only
  • 1.06" heel height

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Men's Classic Break Chukka Boots — Price Tracker & History