15 Stylish Boots for Winter (Or, Resolving My Anxiety About Winter by Shopping for Boots)

October 26, 2014


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Technically, I’ve done winter before. Four times in Chicago, and once in Iowa. And yet, six years in the Bay Area completely obliterated my ability to deal with extreme weather (both hot and cold). Of all the things I’ve been stressing about, my main thing has been maintaining warm, dry, feet. Preferably in shoes that look cute AND can handle the elements.

Here are 15 boots that I’ll be considering this winter:

Rugged Winter Boots

Clockwise from top left: Nike – $100 // Timberland – $150 // Nike – $100 // Khombu – $69 // Sorel – $94 // Columbia  – $120
Furry Winter Boots
Left to right: Sorel – $220 // Michael Kors – $275 // Bearpaw – $199

Everyday Essential Boots

Clockwise from top left: Michael Kors – $250 // Cole Haan – $298 // The North Face – $165 // Michael Kors – $245 // Madewell – $298 // Cole Haan – $278

Luckily the temperatures haven’t gone crazy cold just yet. Are you a winter-weather veteran? What boots do you recommend?
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2 Responses to “15 Stylish Boots for Winter (Or, Resolving My Anxiety About Winter by Shopping for Boots)”

  1. Elizabeth Says:

    Growing up in Wisconsin, winter boots were always a trade off: the warmer and drier your feet, the heavier and heavier (and heavier) your boot. I remember in high school, when my feet stopped growing and I could invest in a really nice pair of Sorels: my feet had never been so happy, but even a short walk was exhausting.

    Then Uggs were invented.* Spring for the waterproof spray bottle, and your feet can be warm and dry in a (comparatively, at least) amazingly light boot. There’s a reason they’re so popular.

    I also have a pair of Uggs-like Merrells.

    (If you’ve never worn Uggs or other similarly-furry boots before: the wool will compress as you wear them, so if they aren’t really, really snug when you first try them on, then they’ll be way too big after a week.)

    *Obviously, sheepskin boots must have existed before then, but I really don’t recall seeing any in Wisconsin. Lost technology, I guess.


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