For a long time I admired Red Wing boots from afar but hesitated because of the price — comfortable taste, modest budget. So when I found an almost-new pair of Red Wing 877 boots at Fox and Faun in Greenpoint, Brooklyn, I didn’t hesitate. They were exactly what I’d been wanting: rugged, well-made, and classic in appearance.
Living in New York City means lots of walking, and I’m usually cautious about taking a new pair of boots out for extended periods. Leather footwear often needs time to break in, and a new pair can rub in the wrong places. These 877s, however, surprised me. Right out of the box they were comfortable. I spent two full days walking across Manhattan and Brooklyn and didn’t get any blisters or hotspots. The boots felt solid underfoot: the 8-inch shaft offers substantial ankle support without feeling overly bulky, which is important when you’re covering long distances on pavement or navigating crowded streets.
Beyond daily walking, I’ve also put these boots to work. I spent a day in my workshop clearing out a pile of scrap lumber, loading tires, moving crates, and carting wood to the recycling center and the dump. The 877s handled it all. They deliver reliable protection and are durable enough to withstand rough tasks. The leather holds up and the construction gives confidence when you’re handling heavy or awkward materials. If a task requires a puncture-resistant toe, I’d pick a dedicated steel-toe boot instead, but for most general work and urban wear these Red Wings are more than capable.
Style-wise, the 877s are versatile. They pair well with jeans, chinos, or heavier work trousers and have a timeless look that complements both casual and more rugged outfits. The burnished brown leather has a character that only improves with age and wear, and the build quality makes them look purposeful rather than purely fashionable. They provide a balance between form and function that’s rare at this price point for new boots, and finding them used was a fortunate bonus.
If you like the 877, you might also consider the Red Wing 875. The 875 is slightly shorter and can be more comfortable for extended urban walks or for people who prefer a lower shaft. Both models share the same heritage and construction quality, so the choice comes down to personal comfort and the intended use. The 877’s taller ankle support is particularly handy if you do a mix of walking and manual tasks, while the 875’s lower profile can feel lighter for continuous city use.
One of the strongest appeals of these boots is their American heritage. Red Wing has a long history of producing durable footwear in Minnesota, and they continue to craft and repair these models at their factory. That commitment to manufacturing and resoling keeps these boots out of the disposable footwear category and contributes to their long-term value. Owners often keep their Red Wings for years, opting to resole and renew them instead of replacing them — a practice that fits both sustainable and practical wardrobes.
For anyone debating whether to invest in a pair, consider how you plan to use them. If your days are mostly on pavement but you still want something that can handle the occasional heavy task, the 877 is an excellent compromise. If you’re primarily walking long distances, try the 875 for a slightly lighter feel. And if you need toe protection for industrial work, look at models designed with safety toes.
In short, these Red Wing 877 boots deliver comfort, durability, and classic style. Finding an almost-new pair at a local shop was a stroke of luck, but even at full price they make a strong case for being a long-lasting wardrobe investment. They’re proof that well-made footwear, cared for and occasionally resoled, can outlast trends and remain reliable day after day.