Red Wing Men's Weekender Chukka Boot
The Weekender Chukka is a favorite for its laid-back styling and comfort straight out of the box. It looks the part in the office or off-the-clock, and it feels so good you won’t want to take it off.
The Weekender Chukka combines casual style with all-day comfort. The boot is supremely comfortable straight out of the box thanks to lightweight, flexible stitchdown construction. Worn with or without socks, the Weekender Chukka channels a relaxed warm-weather vibe that’s so comfortable you won’t want to take it off. The boot’s Hill outsole provides steady footing and sleek styling.
FIT INFORMATION
A new pair of Red Wing Heritage footwear should fit comfortably tight on the foot, with enough room to freely wiggle toes. As you wear the footwear, the full-grain leather upper, insole, and cork midsole will mold to your feet, creating an increasingly personalized fit over time. We recommend trying on footwear in-store to ensure proper fit.
NO. 60 LAST
- * Designed for stitchdown construction specifically for the Weekender Collection.
- * Creates enough room in footwear to add footbeds to adjust fit.
Free Delivery
Free Delivery and Returns.
Free returns
Free Delivery and Returns.
Authorized retailer
Free Delivery and Returns.

Shop with Confidence – We're an Authorized Retailer
When you buy from us, you’re getting 100% authentic goods directly from the brands you love. As an authorized retailer, we guarantee genuine products, and for select brands, your purchase may even be covered by the manufacturer’s warranty. No fakes, no risks—just peace of mind knowing you're getting the real deal from a trusted source.
Absolutely! As an authorized retailer, we only sell brand-new goods in their original packaging, complete with any accessories, extra laces, or special inserts the brand includes. No sketchy repackaging—just the real deal, straight from the source.
We get it—finding the perfect fit can be tricky. That’s why we offer a hassle-free exchange policy for unworn sneakers in their original condition. If you need a different size, we’ll help you get the right pair without the runaround.
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