Anyone have a winter boot (ankle high) they like? I bike 3 miles, train 30, then walk another 3 every day. These Chicago winters throw everything at me... and I love being prepared. Also, I don't like carrying a change of shoes, so they'd need to be comfortable enough for the casual urban dress code at my office. Waterproof would be nice, but at least water repellent.

Considering these (but would prefer black):
https://www.zappos.com/blundstone-bl490-brown

Anyone have a winter shoe/boot they love?

I've used a generic waterproof pair from Walmart and they work great. They're more of a hiking boot style. You might also ask in the winter forum.

Any decent pair of hiking/work boots should work for you. On REALLY cold days (like -20 windchill or more) I will slap on my work boots. They are pretty much plain brown, so they match well enough with khakis (certainly better than any sporty bike specific pair). I've found that socks are more important than shoes for staying warm in winter (wool).

the boots in the link are nice (very nice), but the pull up straps would be annoying when your pants get caught on them.

3 mile walk!!! Are you mad!!!!
Can your train accept a large folding bike such as MTB wheeled Montague or Dahon. These can take winter tyres.

Ha! funny. As a former subject of the Queen myself, I find this funny coming from a Brit. No offense at all. I just always thought the English enjoy a good walk.

I have some sorrel boots, good to about 0F that work well, ankle height and waterproof, good tread on the bottom.

There are 20" studded tires too, so a small wheel folding bike can go on the train with you..

+1 on the Sorrells , I have an LL Bean boot for winter use, freeze-up is an episode,
here, though, not a quarter of the year.

For me, winter is about surviving so I ride with Sorel sub freezing boots on my bike. I worked in an office with a dress code but in January and February everyone just wants to live and no one looked askance at winter boots. The Blundstone's look great but not terribly warm and you're in Chicago, land of fierce winters. How about these?

Try a pair of LLBean snow sneakers, have used a pair winter commuting for years -

I have, er, had, a beautiful pair of Blundstone chisel toes that were perfect for fall riding: comfy, light weight (lighter than the ones the OP linked to), waterproof... great boots. got them out of storage the other day only to find that a rodent had made a meal of the heal on one and a chunk of soul on the other. I'm absolutely crushed (at least as much as I can be over clothing. :shrug: ).

I'll either resort to my Company Boot from 5.11. It's about the same weight, comfort, water resistance as the Blundstone the OP linked to.

Here's another to consider: Company Boot 2.0. Looks good.

Waterproof? Slightly oversized for adding another sock layer? and having wiggle room?
Fits into clips or Power Grips?
Black leather tends to show salt stains, but those can be removed with saddle soap followed by some mink oil or black shoe creme.

Is it possible to simply wear your snow boots on your commute and leave a pair of dress shoes at the office?

Otherwise, would you consider a pair of galoshes/overshoes?

Anyone have cycling shoe covers, for example Pearl Izumi, Showers Pass, or Sugoi?

I use these: MEC brand shoe covers. They work very well at keeping my tootsies warm and dry regardless how long and how heavy a downpour I find myself having to pedal through.

+1 This is standard for me. I leave a pair of shoes at work and transport everything else. Desenex anti-bacterial spray keeps odor possibilities at bay. My work enviornment is office causual/warehouse, so it's not as much of an issue as one who works in a more formal situation.

During cold/inclimate weather I use Lake winter cycling boots w/2 pair of socks. One thin and one 100% wool knee high. Shoe cover options consist of Bellweather, Performance, Look and Nashbar. They're used in combination w/different shoe/sock configurations depending on the type of weather. The main thing if using cycling shoes w/covers is to remember to not use shoes w/mesh insteps as it defeats the purpose of the shoe covers.

It doesn't snow that much here in TN, but if I still lived in Chicago I'd have a rig set up w/Power Grips and low psi wide studded tires, that's for sure. Rubber, wool lined boots and waterproof pants w/elastic cuffs and gaiters, too. Started my cycle-commuting career in the Windy in the beginning of February, so my learning curve was steep. I was on a 3d hand road bike and thought falling down in the slush was just part of the drill.

Thanks, that looks very good. Will go to REI to see if they have something similar. Cheers.

+1 for me as well. Every place I work, I always ask during the hiring process. "I will require a very small place to keep a bike pannier, shoes and maybe a pair of clothes." I dont care where it is, could be the janitors closest, basement, I dont care, but I got to have somewhere.