Insomniac Sale Picks: Winter Boots

*In this late-night feature – which will run Tuesday, Wednesday, and Thursday of each week – I’ll gather up three fun items that are currently on sale online and share them with you! I would LOVE suggestions: Stylish wide-width pumps? Classic v-necked sweaters? Chandelier earrings? Petite dress slacks? What would you like to see featured?*

Amanda requested a few picks for winter boots, so here we go:

baffin judy

Baffin Judy – was $169.99, now $102.99 – $134.99

I’m not familiar with this brand myself, but it’s a Canadian brand and most of the Canadian snowboot brands that get picked up by the big online shoe retailers DO NOT PLAY when it comes to snowboot construction. This pair gets high ratings for comfort and warmth, though do check reviews for info on sizing. Available in brown, black, and this taupe in US sizes 6 – 11, sold out in 10. Size availability varies by color.


Timberland Earthkeepers Savin Hill Tall Boot – was $220, now $197.99

When I think “winter boots,” I generally think of snow boots … but that’s not the case for everyone. Winter is different everywhere, and many folks are seeking weatherproof boots that are still stylish enough for office or everyday wear. And for those folks I have one word: Timberland. Sadly, although this brand creates some D width shoes, they don’t do wide calf tall boots. But they are the only company I’ve found that makes waterproof and weatherproof boots that are utterly gorgeous to look at and totally comfy to wear. I just got these in the mail (my beloved cognac boots do NOT fare well in wet, winter weather) and I’m in love. The pair above is also from the Earthkeepers line, and will work beautifully in business casual environments. Available in brown and black in US sizes 5.5 – 11 including a few wide footbed sizes. Size availability varies by color.


Kamik Soho – was $150, now $98.98

I know that finding wide-calf winter boots can be tough, and what I generally recommend is to find slightly lower shaft and/or lace-up styles. These Kamiks are 15″ wide, and can lace a bit wider as needed. These pups have a temperature rating of -25° F/ -32° C and since we had a 20-below windchill in Minneapolis today, I’m rather tempted by them myself! Available in US sizes 6 – 11 in black and dark brown. Size availability varies by color.

Other not-currently-on-sale resources for winter boots:

  1. Timberland – I’m gonna repeat myself down here, I know, but want to make sure you folks explore these brands in addition to the styles I’ve selected for the evening. Timberland is the only company on my radar that consistently creates stylish, nearly work-appropriate boots that are also water- and weatherproof. Also check Zappos and 6pm for deals.
  2. Sorel – Ruggedly stylish and extremely durable. Some styles aren’t ideal for walks longer than half an hour or so as they scrunch down in the shaft and can cause blisters. These are great commuter boots, though.
  3. Merrell – Wide calf winter boots are tough to find, but Merrell makes several stylish and weatherproof lace-up styles that will give some flexibility. This mid-calf pair is fabulous.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

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10 Responses to “Insomniac Sale Picks: Winter Boots”

  1. Sanna

    Hi Sally, I love your blog! I have long (36# for jeans), slim legs with defined muscles. Could you please help me out on my search for long boots for long legs? Often boots have the calf-muscle curve just below my actual calf mucle and then the slimmer, upper end of the boot cuts right into it.

  2. Nique

    Aquatalia by Marvin K also makes some amazing weatherproof boots that look sleek and stylish. They are pricey, but you can often find some good sales, and they are worth it.

  3. Bridget

    Yes, what is up with the new sorel boots and their heel rubbing! It’s maddening! I have a pair from good ol Fleet Farm back in the day that is so comfy and warm, just not all that pretty. Their other style that I have is way cuter, but it hurts to walk in….

  4. Keilexandra

    I’ll second the recommendations for Aquatalia and La Canadienne, plus add Blondo to the list of stylish weatherproof boot companies. Pricey, of course, but you can catch them on sale for not too much more than a pair of Timberlands. La Canadienne is good for narrower calves too.

  5. Keilexandra

    Don’t forget about Blondo, another Canadian shoe company that makes stylish waterproof shoes.

  6. Marsha

    For those with wider calves and/or feet, consider buying men’s boots. Men’s sizes are typically 2 sizes smaller (if you wear a 9-10 women’s then a men’s7- 8 will probably fit) and medium width for men is a D. The calves are also wider and they’re usually constructed more ruggedly.

  7. Shaye

    My Sorels lace up just fine over my wide calves! I found that sizing up took care of the heel chafing problem. A good option as long as you’re not at the top of their size range.

  8. Patricia

    I love all the steps you’ve taken towards size inclusivity in your clothing posts… but what about shoe size diversity? I know not as many women need extended shoe sizes as need plus-sized clothing… but I wear a size 12 and it’s insanely hard for us to find shoes of any kind, much less cute ones, so your recommendations in these posts would be seriously appreciated! Can’t tell you how much time I’ve spent drooling over the amazing shoes you recommend only to find that none of them are in my size. (That second pair! Swoon!)