Boots v. Booties

Happy fall, y’all! The weather is getting chilly, the pumpkin spice drinks are back, and that means it’s closed-toe shoe season!

Perhaps the biggest mental debate I have in fall is that of boots v. booties. When should I wear my tall riding boots and when should I opt for some booties instead?

I’ve used some outfits from my own closet as well as from my friend Olivia to help illustrate how to decide between boots v. booties this fall!

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Boots are the traditional fall shoe. They generally come in black, brown, grey and beige colors.

Something to keep in mind with boots is that not only do you have to get the correct size for your foot, you must consider the size of your calf. Since boots are generally hitting mid-calf or around your knee, your boot shaft has to be large enough to fit your calf muscle comfortably. Most boots designate sizes with “wide shaft” for those who need a little more room – nothing is worse than boots that won’t zip up!

However, I would argue that it’s easy to find a boot that fits both your foot and your calf! There’s just no replacing the classic fall boots, especially when they make outfits so cute!

Pair With:

Jeans + Sweaters

Sweater Dresses

Leggings + Vests

Shop My Fall Boots Picks



Booties are the hip young sister of the fall boots. Booties are defined as boots that end 1-4 inches from your ankle. Anything above 4 inches? You’ve got yourself a boot.

Booties are a big more edgy than traditional boots because they come in a wider array of colors and patterns. Booties also typically have a higher heel than boots.

You don’t need to worry about a boot shaft with booties – just find a pair that’s comfortable and fits your feet well!

Pair With:

Jeans + Jacket



My Fall Bootie Picks



Now…it’s time for a fabulous giveaway!
I’ve teamed up with an amazing group of bloggers
to give YOU a chance to win:
a $600 Nordstrom Gift Card, just in time for some fall shopping!

Simply enter below by completing the rafflecopter.
You’ll receive one entry per completion.
This giveaway is open internationally and runs until 9/20.
Winner will be announced here. Good Luck!

a Rafflecopter giveaway


hi! my name is Caitlin, and I am a Midwest twenty-something, agency owner, thrifting pro and blogger who shares outfits, wellness, good books and so much more. I am so glad you are here - welcome to my corner of the internet!

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  1. Anna Smith wrote:

    Just entered this giveaway, absolutely loved this post!! The boots you are wearing in the first photo are my favorite, I totally need them for Fall!

    xo, Anna Elizabeth

    Posted 9.13.17
  2. Candace wrote:

    I wish I was tall enough to wear tall boots! I always have to go with booties. Hahaha ☺️

    Posted 9.13.17
  3. Nataly wrote:

    I am loving all your boot and bootie picks! I can’t wait for the weather to cool down around here!

    Posted 9.13.17
  4. I can’t get enough of booties and I think they’ve always been my favorite shoe! I have had troubles finding boots for my calves as I am a plus size but they’re really been showing out with the wider sizes lately! Thanks for this post. And awesome giveaway!!

    Posted 9.13.17
  5. Kristin wrote:

    Such a great roundup! SOOO many fabulous picks. I seriously cannot even narrow down my top 3 favorites from all your options! YAY for Fall almost being here 🙂


    Posted 9.13.17
  6. Lauren wrote:

    I love boots, especially over the knee if possible 😀


    Posted 9.13.17
  7. Joana Castillo wrote:

    These boots and booties are too cute!!

    Posted 9.13.17
  8. Jen wrote:

    I love all the different ways to wear booties and boots for the winter! I love them both! I usually decide based on the weather, if the snow will make it into my booties then I opt for boots! You linked some super cute booties!

    Posted 9.13.17
  9. Stephanie wrote:

    I love both boots and booties, but I’ve gotta say, booties have a special place in my heart. I own way too many pairs and I still want more haha. I have yet to find the perfect pair of OTK boots (that don’t cost my life savings haha). You’ve got such cute options linked here for both!

    Posted 9.14.17
  10. This was such a good post! I’ve been wearing peep toe booties a lot lately, but I can’t wait to pull out the riding boots! I love all the boots you posted. I also love your blog, and I subscribed!

    Posted 9.14.17
    • Caitlin wrote:

      Aw thank you so much Amber!

      Posted 9.14.17

Comments are closed.