Red Wing Heritage Weekender Chukka Shoe Style 3322 Review – $229.99

I’m a pretty laid back guy in terms of style, but when I found myself in the dairy isle sporting sweats and sliders while shopping, I figured it was time to upgrade a bit. I did the usual; substituting v-necks for tees, chinos over jeans, etc. Where I really struggled was over footwear. I  just really like the comfort and ease of gym shoes and didn’t want to go down the casual Oxford route. After some research I happened upon Chukkas, a kind of boot/shoe hybrid that was lightweight, casual and most importantly didn’t have neon blue mesh logos. I’m a fan of American made products and with their legendary boots, I decided to try the Red Wing Heritage Weekender Chukka.


The Weekender Chukkas upper is made from Red Wing’s Copper Rough & Tough Leather. This leather is oil tanned. This gives it desirable properties such as being water, stain and perspiration resistant. It also showcases a more natural look and feel because less finishing materials have been applied. The stitchdown construction means these can be resoled as well. Metal rivets reinforce the shoelace holes, but are hidden from view on the shoe interior. A Texan board is used in the shoe’s interior. The cushioned insole features Redwing’s proprietary Comfort Force impact absorption system and a polyurethane crepe outsole. Shoes weigh one pound each.


The Weekender Chukkas are advertised as ready to go with no break in needed. For the most part this is true, the leather is very supple and flexible. The outsole is also pliable. I almost would have preferred a more stiff leather as I find the initial discomfort of breaking in stiff leather is worth the custom mold to your feet. I followed Red Wing’s suggestion and ordered a half size down, and the fit was pretty accurate with medium thick socks.  Interestingly enough, while the shoe needed no break in, the laces definitely need some coaxing. They were stiff and didn’t hold a knot well. This issue slowly mended itself though as the laces relaxed.

These shoes are definitely more comfortable than a pair of boots. I can walk several miles no problem, and prolonged standing is a breeze. These are definitely becoming my stand ins when I would normally reach for boots.


The Chukka design is pretty universal among shoe manufacturers. With a lot of companies producing a visually similar product, the big differences lay in the small details. Red Wing’s craftsmanship sets a bar that most companies can’t come near. There is triple stitched panels where others use one or two. The shoelace eyelets run on the interior of the shoe for a cleaner look.

These can pretty much go with any jeans/chinos/khakis you can throw at them. Unless you have your hem above the ankle, they’ll look like full fledged boots. I love boots, but I’d definitely prefer the comfort and ease of the Chukkas almost any day, so wearing these is a great way to get best of both worlds. They have that timeless look and just exude quality.


For $230 dollars, you could probably buy 3 pairs of Chukkas from your local mall. However, the motto “Buy the best, only cry once” comes to mind with the Red Wing Heritage Weekender Chukka. Top notch construction means no surprises and the fact that they can be resoled, might make them the more economical choice long term as well. Great looks and comfortable, you can’t really go wrong with them so long as you get the proper size.

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