In the winter months, I find myself in a bit of a conundrum. I can’t wear shoes that expose my feet in any way, shape or form. i’m illogical a lot… But you have to draw the line somewhere.

I’m a big fan of partially-leg-covering footwear. You know, boots. Not all boots are created equal, however. I rarely drive and end up walking just about everywhere. For this, I cannot wear these:

….as much as I might like to. The thought alone makes my ankles twitch.

For walking boots, I require these things:

  • A small heel. Flat boots are okay, but it’s so hard to find some that don’t make you look like Link.
  • A chunky heel. Baby stilettos not only look creepy, but are creepy. And uncomfortable/unstable/all that important stuff.
  • An almond or rounded toe. Square toes and pointy toes have no place on walking boots – or maybe any boots…

Attempting to acquire boots is kind of a scary thing for broke-ass people – don’t you think so? I always assume that I’m not going to find boots I want for less than $150. Fortunately, that doesn’t have to be the case!

Walking Boots under $100

Doc Martens Engineer Boot | $81.80

This is an insane deal. These Docs retail for $130, and they’re on sale RIGHT before winter hits – not a common snag! They also come in some grey/beige/white colors. I can’t decide which I like better.

Steve Madden Troopa Boot | $99

I believe Jen is obsessed with these… I feel like she mentioned it in an issue of the Broken Record in the days of yore, but maybe I’m thinking of another boots. Probably not, though – these are bitchin’.

Blowfish Wright Boot | $69.95

I’m diggin’ the fabric look on this pair… What do you think? Is cloth fabric a boot-appropriate material?

Nomad Matador Boot | 79.95

This is the wildcard selection for this post. Mostly because I like to have names for things. I am oddly attracted to these, and I’m trying to be comfortable with it, but it’s just not working. You can deny that these look awesome, though. You just can’t.

Which would you wear? Do you have snooty walking boot criteria?

Probably watching Netflix.