Stylish, warm winter boots… do these exist?

I’ve been stumped by this problem for a while now.

When I started my first big-girl job, I quickly realized that I needed professional-looking winter boots for my commute to work.  I thought the task of buying new winter boots would be the best thing ever (after all, who doesn’t love a new shoe purchase??) but it turned out to be quite frustrating and disappointing.  If I actually wanted to be warm as I walked to work, I was going to have to suck it up and wear a warm, functional winter boot.


While this would work and keep my feet warm, this option would simply not do – can you image me walking to work, with a lovely suit, stylish wool coat and THOSE boots?! I can’t either!  Needless to say, I ended up getting stylish boots…. that didn’t keep my feet warm for 4 blocks…. but I looked great! Brrrr…

It still amazes me that most winter boots on the market (available to those of us in real winter weather) aren’t stylish AND warm.  Most of the fashion-forward boots I come across wouldn’t hold up for 30 minutes in any real Canadian winter weather.  They just aren’t made for “real” winter.  To me, these are “pretend” winter boots…. like the ones I bought a few years ago.  What a waste of hard-earned $$!!

On the other hand, we have those boots that are perfect for -30 or below (Celsius) but most certainly don’t belong in any urban setting… and definitely won’t go with your outfit as you commute to work each and every winter day!

I thought I would do a bit of digging to find boots that are:

  • Work-appropriate
  • Comfy for commuting
  • Stylish
  • Warm

For dryer winter weather, here’s what I found:


Joan and David Florita Wedge Boots


Cole Haan Air Tali Wedge Boots


Sam Edelman Jayla Wedge Bootie

For those slushy, wet winter climates, here’s what I found:


Sorel Cate the Great


Tapeet Flat Puffer Boots


Michael Kors Brandy Snow Boot

Which of these “real” winter boots suit your fancy?