'Classic' Chukka Boot

I just purchased these shoes and they are fantastic!! My 6th pair of Red Wing products!! I don’t wear anything else!!

This is my second pair of the Red Wing Work Chukka in Briar Oil Slick Leather, and the quality is consistently excellent. The leather has that classic Red Wing feel — durable, rich, and built to age well — and this pair came in a slightly lighter, more reddish‑brown tone than my first, which gives it unique character. The fit is true to my previous pair, with the usual Red Wing break‑in: firm at first, then extremely comfortable as the leather molds to your foot. I wear these for two reasons: they look great, and they’re podiatrist‑approved. After my military service, proper foot support became non‑negotiable, and Red Wing boots have made a real difference in daily comfort. They pair effortlessly with jeans or chinos and strike the perfect balance between everyday style and work‑boot durability. With basic care — conditioner, shoe trees, and patience — they deliver long‑term comfort and longevity. If you want a boot that supports your feet without sacrificing style, this Chukka is an easy recommendation

I love the color of the boots, and their leather scent. They're comfortable and very cute.

Bought this shoe in 2014. I may get them resoled for the second time with Vibram Christy.

I haven't put a whole lot of time in these, but I am so happy with my purchase. I wish I bought them sooner! I have a few pairs of mocs and really wanted something different, but with the same classic style. I really appreciate the EE width, otherwise they might be a little snug, but they feel great. I skipped on the IR and the Blacksmiths because I really love the all-day comfort that comes with the wedge sole. I am a science teacher, so I'm on my feet all day and the concrete floors really take a tole on your feet and back...man I feel old saying that. I also wanted something that was a little more forgiving in the warmer weather we have here in Texas. I wear my mocs ALL the time and didn't realize how much cooler a shoe REALLY was until I picked up the Shop Mocs, but that is another story. I am looking forward to putting these things through their paces and am so happy I finally picked them up!

Bought this boots about year an half ago, boots are great the only downside is sole went out within 6 months and to pay 150 to resole them plus the 300 that you already spent in my opinion a little pricey

Two comments of note: 1) Comfort from day day one (2) top drawer constructio, though I wish they were lined

Brought a second pair for Jobsite meetings Kept my first pair for working around the house Made in the USA

I originally purchased the work chukka in 2017. I wore it almost every day. Resolved it 4 times. Built four buildings during this time. Best boot I ever owned, hands down. When I decided I need a succession plan for when in the future I might need to retire them, I again purchased the work chukka. Only red wing changed the design. Now the boot doesn’t fit!!! I needed tried every size. Ended up settling on a size that wasn’t a good fit. I’m very frustrated and disappointed. Not sure what to do here. I’m stuck with bad fitting boots. Will probably toss them and get something else. Bad move Red wing. What happened to my favorite boots?

Have had mine for nearly 10 years with near daily wear, and still holding up great. Please bring back Oro so I can get a fresh pair!

I highly recommend these boots. They are of excellent quality and fit. They wear like iron and can be resoled by Redwing. I've been had mine 3 years of nearly constant wear.

I heard this style shoe is being discontinued. I usually get them in the copper red color. Please please please don’t stop making this shoe. I wear mine almost daily, they’re a great all around shoe and look better as they age.