Red Wing Cycling Boots: The Best Winter Riding Footwear

Please note, this isn't an infomercial for Red Wings. I wrote this article because I couldn't find one like it while boot shopping last year. I wasted a lot of time trying to find the perfect boot for cycling and casual use, but hopefully y'all can avoid that. At any rate, here be the best thing to put around your feet if you ride around on a bicycle in the winter:

I ride BMX pedals on my city bike because they dig into my shoes to hold firm and are easier than clips to stomp on and off of at traffic lights. And in the winter, clipping in can be a hinderance, which anybody who has ever slipped on ice and failed to unclip and then separated their shoulder on the cold, cold ground can attest.

Flat tennis shoes and skateboarding shoes work best with platform pedals, but in cold/watery weather they leave my poor little ankles exposed, so I switched to boots:

Too much tread! 

Ah! but boots have heels and hard, thick tread that doesn't allow much purchase on a BMX pedal.

So I bought thin, flimsy boots with light tread, but they wore out quickly:

Buy cheap means buy twice

Which is how I got to the perfect cold weather riding boot, Red Wings:

Red Wing boots are made in Minnesota out of thick leather with heavy-duty stitching. They're designed to outlast the foot that fits in them so that workmen can pass their boots down to the next generation. They're also repairable, and the soles can be replaced or switched to a different style if the needs of the wearer change.

What makes this specific Red Wing boot (the 6" Classic Moc with the 'Traction Tred') a good cycling shoe is that it has a thick flat sole, like a skateboarding shoe:

And the conditioned leather on the upper repels water and wind while being durable and abrasion-resistant. The perfect boot.

There are some provisos, however:

For one, the cost. Red Wings aren't cheap. The ones in the picture have a small defect so I got them for a discount, but the retail cost of a new pair is around $300.

For another, since they're leather, they need to be cared for, much like a Brooks saddle.

And for another another, if you plan on walking in your Red Wings, they have to go through a break-in process that takes months, if not years.



     Some notes on breaking Red Wings in for cycling:

Straight out of the box my 6" Red Wings did not need to be broken in for bike riding. The main ankle movements in cycling are minor, and involve rotating the foot up at the top of the pedal stroke, and down on the back-end of the stroke, which medical nerds call dorsiflexation and plantarflexation:

Some cycling guides – like the one below from Bicycling Magazine – recommend reducing ankle movement as much as possible so that you can focus on developing the larger joints and muscles of the leg:

With that in mind, the stiff, un-broken-in leather of a new Red Wing boot works fine for cycling.

But for walking, hiking, and working – Oi. I've had my Red Wings for about eight months now, and they still give me blisters if I walk for more than a mile in thin socks. Granted, I don't walk in them that often, which is why they haven't molded to my feet yet.

And one other thing, the 'Traction Tred' sole is thick. I had to raise my saddle about an inch.


Oh yeah, and I guess I should bring up the fact that there exists an actual Red Wing Cycling Boot:

It's made in conjunction with another Minnesota shoe company, 45 North. I'm sure they're fine. I won't get a pair though. I already have some overpriced Mavic clipless boots that I never wear, and the reason is simple: who in their right mind clips-in on snow and ice? Extreme weather riders know that one's foot spends almost as much time on the ground as the tires on some excursions, and anything that hampers a quick foot-down is a liability. But I don't know, maybe some people just don't fall as much as me. It's also nice to clip in so that your foot position doesn't change over big bumps and stuff. To each his own. 

And so:

You don't need much in a winter cycling boot except basic wind/snow resistance and a flat sole. But why not get those things with a little heritage-level style? Red Wings do the job, last forever, and look good. Git sum.