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Suggestions on Leather Boots in Chicago Winters?

Halflegend

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Hello all! I'm a long time lurker and first time poster on SF. I've been a fairly active member of AAAC for a few years (under the same name) but thought you guys would have some better advice on my specific dilemma.

I'll be moving to Chicago next month to start schooling. I'm in a fairly urban area but have a 10-15 minute outdoor walk to get there. I wanted a pair of boots that I can wear around campus for the next four years. I've thought about Bean boots and the like, and while that is the most practical option, I love leather shoes. My daily shoes are a pair of dark brown plain toe brogues. I'd like a pair of shoes that I can wear casually around the dorms, to class, and to semi-formal affairs with a shirt and tie. Essentially a go-to shoe in winter. Kind of a penny-loafer for winter.

What I'm looking for:

  • Under $350, I can dip into summer work money, but only if it's an extremely rare deal.
  • A dark brown color (my watch strap, belts, wallets are all a dark rich mahogany color, I'd love to match my boots too)
  • Waterproof!!!
  • Warm but not outdoor camping levels of insulation. I'll probably wear thick socks underneath but all of my classrooms/dorm halls are heated so I don't want to be sweating while in class.
  • I'm a sucker for white/off-white wedge soles. If I can't find one that works, a natural color tan sole would be okay too.
  • Shoes that age well


I found a few that I really liked the looks of:
Loake
OakStreet: This, and This (Both of these soles look perfect to me, wouldn't be disappointed with either)
Wolverine 1000 Mile

Unfortunately, I don't know how well any of these will hold up in winter, how they'll age, or if they're worth the money. And a few are out of my price range as well, but I hope these are enough to give you guys an idea of what I'm looking for.

Once again, thank you guys! I really appreciate any advice/brands you can offer.

Best wishes,
S.


tl;dr? Undergrad male looking for a good value $300 brown leather boots that'll rough an urban winter for a couple years.


Quick Edit: I did a search and looked through the relevant threads to find the suggestions that I linked above, but if I missed a thread similar to mine, do let me know!

Many other threads suggested a cover up or a change of shoes. Id prefer to carry as little as possible to class, so for practicality reasons I'm stay away from that option.
 
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