Laid back comfort out of the box, the Weekender blends timeless style with seasonal versatility. From easygoing days to memorable nights, these boots are made to live off the clock. Every …

Off-the-clock shoes with a workhorse pedigree, the Red Wing men's Weekender Chelsea boots are handcrafted in the USA with durable, premium leather for years of post-work adventures.

Make the most of your downtime with the sleek, off-the-clock comfort of the Weekender Chelsea boots. The most relaxed Chelsea silhouette in Red Wing’s line today, its stitch-down …

Mar 1, 2024 · Red Wing's best known Chelsea boot is not as sturdy as their work boots, but they're lightweight, flexible, and great for the city.

The Red Wing Men's Weekender Chelsea Boot combines rugged durability with sleek, modern style. Crafted from premium leather, these boots feature an elastic side for easy on-and-off …

Jul 26, 2018 · Experience effortless comfort with these Red Wing Men's Weekender Chelsea Boots. Crafted from premium, full-grain leather, these ankle-high boots feature a sleek, relaxed …

Dec 9, 2025 · Bring a bit of sophistication to your casual weekend plans or opt for a more laid-back look at the office with the Red Wing Heritage Men's Weekender Chelsea Boot. Classic …

Made in the brand’s Plant 2 heartland in Red Wing, Minnesota, this timeless design is crafted from premium rough and tough leather, featuring elasticated side panels for an easy-going wear.

Designed for stitchdown construction specifically for the Weekender Collection. Creates enough room in footwear to add footbeds to adjust fit. The Weekender Chelsea is built for making the …

Red Wing's sleek and relaxed Weekender Chelsea is a stitchdown, pull-up boot made from oiled full grain leather which provides a lightweight and flexible feel.