
Here at this Brooklyn style blog, we’ve been talking plenty about the best fall style essentials, the selections you simply can’t live without this season — from the ground up, starting with the best boots for men and carrying on through to essential base layers, waxed jackets and more.
But let’s circle back quickly to the boots you’ve got on your feet, perhaps even right now, as it’s high time to slot in some much-needed boot-wearing as a functional change of pace from summer’s trusty canvas sneakers and leather loafers.
Welcoming the brisk climes of fall is made all that much better, easier and more stylish if your footwear is up to par, be it for cabin weekends away, afternoon walks and even days at a more casual office or a coffee shop.
And with their positively legendary design, hard-wearing specs and versatile good looks, the Red Wing Heritage Weekender Chukka Boots absolutely qualify as both a certified fall style classic and some of the best boots for men, period. The even better news? You can pick ’em up as part of a full-on fall #OOTD via the good folks at Huckberry.
Naturally, like other selections when it comes to the goods being sold by Huckberry, the handsome, rugged and highly functional Red Wing Heritage Weekender Chukka Boots are as overbuilt as it gets, in the best way possible.

The beauty of the highly durable, expertly crafted Red Wing Heritage Weekender Chukka Boots lies in both the details large and small, like the flexible and lightweight Hill outsole, with a textured design for traction and durability (just like other pairs of Red Wing work boots, as luck would have it). That outsole meets hard-wearing leather or suede across four varieties of boots.
Now, if ou follow me on Instagram, you might have seen I’ve tried the White Sand Mohave variation of the impossibly comfortable, sturdy and stylish Red Wing Heritage Weekender Chukka Boots — just check ’em out above. I’ve found these chukka boots to be incredibly lightweight and supple out of the box, yet fashioned with a tough, dependable design — the three-eyelet build and rather chunky outsole make them an expert casual style move alongside everything from rolled chinos to light wash jeans.

The use of Copper Rough and Tough leather, which will develop an eye-catching patina over time, makes the Red Wing Heritage Weekender Chukka Boots a major winner in my book of rugged fall style for guys, too. And since they’re sold by Huckberry at the moment, you’re getting a guarantee of quality, reliability and utterly timeless style. The next time you’re searching for a pair of the best men’s chukka boots, the Red Wing Heritage Weekender Chukka Boots should be your new go-to, my friends.