Wearing Your Boots: Part I

That’s right, homies. By special request, I’m going to put together possible outfits to go with your winter boots. Now, I’ll make no bones about it–I am not a stylist. Despite my unhealthy shoe obsession, most days I roll out of bed, wear whatever’s clean, and then get my butt to work. That’s not to say that I don’t have an eye for textures and shapes, but let’s just put it this way: I would be a terrible candidate for a What I Wore sort of blog.

Now that my disclaimers are over, here are some of my recommendations for types of clothing that you can wear with boots.

Part I will cover ankle booties and “shooties” (shoe-bootie-thingamajiggers), and Part II (tomorrow) will cover tall boots.

So, here it is.

Don’t laugh.

And feel free to offer critique or other suggestions.

Do you love a cute vintage look? Put together this runway-ready look with a base of cool open-toed brogues stilettos like the Report Ellis. Combined with a flowy and tuelley skirt and bold colors and soft cardigans, you’ve got an adorably timeless look. Top it off with a coolly feathered headband for an extra-whimsical air.

One of my truly fashionably gutsy friends has this great pair of flat ankle booties she wears with everything. And by everything, I mean her fabulous collection of Anthropologie dresses, because that’s what she mostly wears.

These BC Mixmasters sort of resemble this comfy, flat style of boot. Do you totally love the wrap-around and tie shaft?? So it’s girly, but still a little rough-’n'-tumble around the edges. Soften it up! Pair it with something unexpected, like a flowy dress and bolero, sheer polka-dot tights, and golden jewelry.

Finally, sometimes it’s easy to underestimate the gorgeousness and class of a simple outfit with few pieces. This runway look features a poofy bridesmaid/cocktail dress and patent ankle booties.

To duplicate this look, try on a pair of the Steve Madden Vulture stiletto shooties. Then show off your legs with a short and gauzy silk or satin cocktail-length dress. While this is definitely a more formal, evening look, it’s a fabulous twist to stray away from the normal strappy sandals. The closed-foot ankle boot mixes it up and adds extra texture.

STAY TUNED for tomorrow’s sets on tall boots. :)


  • Lauren

    you flatter me!

  • Lady D

    Great post! I just realized what’s been missing in my life…Shooties….lol. And as far as suggestions go, what about knee length boots? or the very daring thigh high boots?

  • Danielle

    @ LaurenLauren–Oh stop!! You ARE tres fabulous!

    @ Lady D–Check back tomorrow for another installment addressing sky-high boots!

  • knighttcat


    i was wondering how everyone gets those guess boots? i would love a pair ahah

  • Carol

    I REALLY love the vintage inspired outfit, those shoots are awesome but there is no way I could walk in them!!!
    Carol x

  • danz

    The first and last outfits are my favourites…too cute!