The Search for Winter Boots

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I’m not sure what it is about me and basics in black (we all remember the jeans dilemma, oui?) but when it comes to choosing what should be simple wardrobe staples, I find myself paralyzed with options. It happened again recently with my search for winter boots. 

Yes I live in Canada, where winter is an undeniable fact of life, but the last few years haven’t been particularly snowflake-filled and I’ve somehow managed to survive without a proper winter boot. But this year, when Mother Nature threw a snowy tantrum in the middle of December, I figured my luck had run out, and it was time to find some boots.

I searched high and low (translation: every shop within walking distance on Queen Street, plus some serious scouring of the digital realm) and evaluated each option based on these three questions:

  1. Are they comfortable?
  2. Will they keep me warm and dry?
  3. What’s the back story?

Numbers one and two are pretty obvious, but number three might require a bit of explanation. You see, every piece has a back story – the story you make up about the person who might wear it, or more specifically, the person you’ll transform into if you add this item to your wardrobe. For example, if I put on these boots am I an off-duty hipster NYC model? Or am I a PTA mom with sensible shoes? Will these moto-inspired boots look ironic? Or aggressive? It’s a fine line you see. (As a side note, why don’t we ever see any street style shots in snow? Have you noticed that? Oh sure, the glitterati practice their version of “winter” – fur and layers – but you never see them standing knee deep in a snowbank, trying to wipe the salt from their Jimmy Choos. I knew fashion wasn’t designed for winter.)

I narrowed my search down to these four weatherproof (and hopefully winter-proof) options and then did a totally scientific poll of friends and family (natch) to get their opinion. 

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Eenie – Allique Alexia boot (on sale for $179.99).
Meenie – Kodiak Sage boot ($199.99).
Miney – Blundstone Chisel Toe boot ($179.99).
Mo – Allique Alain boot (on sale for $179.99).

Which ones emerged victorious? Was it the moto-chic with hardware accessories where the back story involved the sartorial savvy of Olivia Palermo mixing uptown and downtown chic?

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Or did the streamlined classics win out, where the back story was the effortless cool of a Parisian mademoiselle, with a closet full of classics in cashmere and wool?

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In the end it was moto by a buckle. The Blundstones will have to wait, but since they’re a classic that’s been around pretty much since the beginning of time (or more accurately, since 1870), I’m confident they’ll be there when I’m ready. Now I’m locked and loaded for the season. Bring on the snow. 

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