Best winter boots for an urban teacher?
October 14, 2009 4:01 PM   Subscribe

Best winter boots for a teacher who has to both get around the city without looking like a huge dork, and stand outside on the playground for long stretches with the kids?

I'm in Canada (Toronto GTA) and winter is approaching. I teach in a small private school and have outdoor playground duty every single day. That is a lot of standing around outside! My more fashion-ish boots from last year did not hold up very well.

This year, I am giving in to nature and dressing appropriately. I want dry, warm feet. I want boots that don't leak. They must be moderately comfortable for walking (to and from subway/bus stop, to the store etc. note: I don't drive so I *will* be out and about in these) and high enough to keep my pants dry on unplowed streets. They must be suitable for both sport-like outdoor winter things and for something like playground duty where I'll be standing around. They must be under $200 (or so). And finally, I am okay with looking like *somewhat* of a dork, but if they are halfway decent-looking, that would be a nice bonus.

So, brands? Model numbers? Best prices? Where to buy in GTA? I welcome any ideas. I am really ready to invest in something proper that will last me a good couple seasons.
posted by JoannaC to Clothing, Beauty, & Fashion (29 answers total) 15 users marked this as a favorite
The answer to your problems. I have the "Regent" in black, but they come in all sorts of other colors that look great. I've never paid so much money for shoes, but once I bought them winter had nothing on me. Slush puddles, wind chill, piles of snow. None of it mattered. They look clunky but they actually look pretty good. They are ridiculously comfortable and even coming with their own fleece lining socks.
posted by foxy_hedgehog at 4:06 PM on October 14, 2009

Why not leave a pair of 'playground' boots at school?
posted by rokusan at 4:08 PM on October 14, 2009

When I reached the 'giving in, dressing appropriately' stage I got a pair of Sorel Joan of Arctic boots and I've been super-pleased. They are on the clunky and overwarm side if you are going to be indoors for several hours in them -- think Xmas shopping -- but otherwise great. They've been through a lot of snowdrifts and come out looking new. I bought them from Cabela's, but later saw them at Sears [Canada] and the Bay.
posted by kmennie at 4:18 PM on October 14, 2009

I do see a lot of fashionable girls striding around in Hunters, even when it's not raining. They always kind of look like wellies to me, but not dorky.

I'm all about my Frye boots, myself. They're a little heavy, but still comfortable for clonking all around town. I live in the Midwest and I don't drive and I take public transit and walk a lot, so I have the same concerns you have. They're both fashionable AND waterproof AND they last forever. Classy enough for a meeting, sturdy enough for tromping through a puddle like you're queen of the slush. Seriously, I expect to be rocking my Engineer 15Rs in the retirement home.

These two pairs are fresh to death and clock in right around your limit. Keep in mind that Zappos is generally NOT the best deal, just the best selection. If you pick out a pair, google the model to find a cheaper price. I see them in hipster resale shops a lot as well, since as I mentioned before they last forever and even secondhand ones look great.
posted by Juliet Banana at 4:19 PM on October 14, 2009

I know a lot of people who swear by sorels and I've had a couple of pairs of merrells I really liked, but might not have been as warm as you're looking for. Zappo's carries a decent number, too, witch is nice for the free return bonus.
posted by mercredi at 4:22 PM on October 14, 2009

Also, I have Frye boots that I love, but most of them aren't insulated, AFAIK.
posted by mercredi at 4:24 PM on October 14, 2009

I've always had good luck with Blondo. I've literally never had cold toes while wearing a pair, and my black ankle-length boots are about to enter their third winter. And Globo sells them, so they're really easy to get. Good luck!
posted by LN at 4:27 PM on October 14, 2009

I have the Sorels kmennie linked to and I always get compliments on them. I, too, am a teacher (albeit one without playground duty!) and I wouldn't want to wear these inside while teaching all day because they are heavy and warm, so I'd probably pack a pair of regular shoes to wear in my classroom. Nevertheless, I recommend the Sorels.
posted by katie at 4:30 PM on October 14, 2009

I have these in black, and my god - they're single the most comfortable thing I've ever worn on my feet, bar none. It almost feels like you've got really supportive sleeping bags on your feet. They even look pretty cute on, especially over a pair of straight-leg jeans. And they're incredibly warm.

The only part of winter I'm looking forward to are those boots.
posted by you're a kitty! at 4:48 PM on October 14, 2009

I've had really good luck with the Timberlands I bought a few years ago. Mine are short, but these might be more what you're looking for.

Just have to put in a good word for Zappos. You may be able to find the boots cheaper elsewhere, but Zappos ships for free (both ways if you need to return them). So when you factor in the shipping charges if you get them from some other site, the price usually ends up being about the same. Plus, every single time I've ordered from Zappos they've upgraded my (free) shipping to next day or second day. Okay, I'll stop. I just love Zappos.
posted by Evangeline at 4:54 PM on October 14, 2009

Bos & Co. have a selection of waterproof boots, that are the most stylish waterproof boots I have yet to come across. Here's a PDF of their winter collection. Last year's collection was somewhat better, so you might find something at the outlet store in Burlington, which I've never been to since it's too far for me to get to. I'm not sure about their warmth, but warm woolly socks should take care of that. I wore them last year and was extremely satisfied. You do have to treat them regularly to maintain the waterproof coating.
posted by waterandrock at 4:55 PM on October 14, 2009

I have this pair of Lands End boots that I am in love with. They're not particularly dressy, but they come in multiple heights and widths. They are comfortable, waterproof, and wonderfully warm.
posted by honeybee413 at 4:57 PM on October 14, 2009

I have a pair of hush puppies waterproof boots that are very comfortable and cute - the ones I have aren't on the page linked, but I got them well over a year ago, so they probably don't make them anymore. I've worn the hell out of them, and they still look like new.
posted by 5_13_23_42_69_666 at 4:59 PM on October 14, 2009

Oh, for retail you can buy Bos & Co. at Balisi and Trove.
posted by waterandrock at 5:01 PM on October 14, 2009

I used to wear these to and from work, then out on the playground with the kids. Cozy, not too ugly, lasted forever.
posted by dzaz at 5:21 PM on October 14, 2009

Just saw an ad for Mark's Work Wearhouse for their boots that prevent falls and are waterproof -- they're on sale right now for $110.
posted by pised at 5:48 PM on October 14, 2009

I lived in Montreal for 10 winters, and La Canadienne are the only brand that have satisfied my fashion/waterproof/warmth needs. They are over your price range ($300-ish full price) but to me they're worth every dollar, since they really are the best. La Canadienne boots will also last several seasons if you get them re-heeled and re-waterproofed each year. I'm not sure where to buy them in Toronto, but they should be readily available at The Bay or comfort shoe shops.

Hush Puppies would be a cheaper, but less fashionable, alternative!
posted by exquisite_deluxe at 5:56 PM on October 14, 2009 [1 favorite]

I just got a pair of these.
So far, so ridiculously warm and comfortable (AND waterproof).
posted by ilikecookies at 5:57 PM on October 14, 2009

Seconding ilikecookies - if I lived somewhere that got even slightly chilly or wet, I'd get some Keen Bern boots.
posted by chez shoes at 6:50 PM on October 14, 2009

I had these last winter and I think they saved my life while I waited for many, many buses in a Boston winter. They are not the most stylish, but they are very warm and comfortable, and the height (almost knee high) really helps keep you warmer. I even wore skirts and tights last winter! They should work for hiking, too.

Whatever you get, you want to make sure it's lined with fleece or felt or something. I love all my knee-high leather boots, but when it's damp they are just not warm enough.
posted by min at 6:53 PM on October 14, 2009

I have The North Face Arctic Pull-Ons and I'm really looking forward to winter so I can wear them again. I put every single other pair of shoes away in the winter now. You might leave a pair or two at work to change into. $100 at Zappos & highly recommended.
posted by theredpen at 7:01 PM on October 14, 2009

I'm currently lusting after these Merrells. The reviews seem promising.
posted by librarina at 8:09 PM on October 14, 2009

I wear Bogs, which are both warm and have a handle for peeling them off.
posted by melodykramer at 8:13 PM on October 14, 2009

Blundstones are what all the cool kids wear.
posted by KokuRyu at 8:55 PM on October 14, 2009

I have the Fryes Juliet Banana mentions, and they're no match for slush and cold. Plus I skid around on ice with them. (JB, I agree that they're beautiful boots, but they're not for hanging around outside in winter Especially not in Chicago. Tried it last winter. Not. Good.).

I do like the Merrells that librarina linked to.
posted by runningwithscissors at 10:13 PM on October 14, 2009

Dittoing the Merrells that a bunch of people linked above -- I live in upstate NY, and they kicked ass last winter. Insulated, waterproof, sick comfortable -- and you can wear them with a dress.
posted by kestrel251 at 6:29 AM on October 15, 2009

There are so many gorgeous suggestions in this thread...I'm almost ashamed to weigh in with these humble Columbias. But oh boy are they nice!
posted by BostonTerrier at 6:37 AM on October 15, 2009

kmennie: I'm not the original asker, but I just bought those Sorels you linked.

It is as though my feet are wrapped in heavenly clouds! So awesome. So, so awesome. I'd recommend the Sorels.
posted by flibbertigibbet at 6:16 PM on October 19, 2009

If you can find them, Icebugs are super great. Here in Denver, ice is an issue. They're like magic.
posted by Carmody'sPrize at 9:33 AM on October 22, 2009

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