How To Wear Boots with Dresses

I’m a Texas Girl.

Boots are a part of my life, and they have been for as far back as I can remember. Way back when, it was me stomping around in my Dad’s boots…

in Dad's boots

while some things have changed, my obsession passion for boots hasn’t.  What kind of boots I wear, and what I wear my boots with has changed.

Boots in other places are a ‘seasonal item’. In my life- they’re an all the time, any occasion item.  I wear my boots Summer, Spring, Winter, and Fall – I wear them with skirts, dresses, and jeans.

Corral Boots and Sundress

catching a little sun at the Food and Wine Conference in Orlando

Last month I was contacted by Country Outfitter, they asked if I’d like to partner with them and talk about how to wear boots and dresses.  I, of course, jumped at the chance.  I’m not a fashion blogger, but I know my boots and dresses!  I threw out the question on Facebook “Boots and Dresses, What do y’all want to know?”  the most common response was “How do you know how to pair them?” followed by “How do I choose the right pair of boots?”

How do I choose the right pair of boots?

Every pair of boots is different, and every person is different.  If you’re lucky enough to have a boot store near you take a good pair of socks, grab a salesperson and start trying them on.  Try on square toe, snip toe (my favorite), round toe, pointed toe and walk, jump (yes), do a little two step in them around the store.  Trust me, they’re used to it, they’ve seen it all.

One good hard rule of thumb – do not skimp on the boots.  You will get what you pay for, and if you buy cheap boots,  your feet will pay.  You don’t have to buy $500 boots off the bat, unless you want, and then go for it.  You want the boots to fit a little snug, the leather will stretch a bit as the boots shape themselves to your feet.

If you don’t have a boot store, come visit me! I’ll take you! 

Once you know your preferred style and size – you can shop from the comfort of your couch :) which rocks

Here are my boots – You can see that I prefer snip toe, and fun colors and patterns.  My boots are a mix of Corral (which are reasonably price and extremely well made) and Old Gringo (which are more expensive, but fit like you’ve been wearing them for years from the get go). y’all should see my husband’s boot collection, it spans the entire top of our closet!

My boot collection


I know my size (9 1/2) and that I prefer my shaft height (the height of the boot up your leg) to be between 11″ and 13″.  I like my boots to hit me around the middle or top of the calf, but not go up to my knee.   I do have the one “shortie” pair, and I wear them with a couple of sundresses, but I’m actually not as fond of that height so they don’t see a lot of daylight.

*  Save and spend a little more on boots, unless you find them on sale, be willing to spend at least $175.00.   Boots are an investment, and they will last you YEARS!

How Do I Style Boots and Dresses?

There is no hard and fast rule.  I wear mine with short dresses that fall mid-thigh, long maxi dresses, and dresses that hit just at the knee.  

Short Dress, Boots, and Denim Jacket

Old Gringo Boots with Purple Target Dress and Denim Jacket

This is a perfect outfit for date night, family day, or girl’s night out.  A fun little purple dress, Old Gringo Boots, and my trusty denim jacket.  The Shaft Height on these boots is 13″ and the heel is 1 5/8″

Medium Length Dress with Boots and Denim Jacket


  How to Wear Dresses with Cowboy Boots

This is a little sassier – it’s a sleeveless dress that falls just below the knee, has a great swing to it.  I paired it with a belt (hello waist definition!), a denim jacket, and my favorite Corral Boots. Shaft Height on these boots is 12″ and a 2 1/8″ heel.

Long(er) Dress with Boots

Long Dress and Boots


Not really showing any leg here, but still showing off my boots!  What’s the point of pretty boots if you can’t see them!?  Even if it’s just a peep of the toe showing :)   These are the same Corral boots as above, because they have so many color variations in them, they are great to pair with all different outfits.

So what’s the rule for boots and dresses?  What’s the perfect How To? 

Here it is…

Are you ready???

Have fun and be comfortable!

Feeling confident and loving what you wear, makes any outfit look good!  Gorgeous boots, are the perfect accessory for just about any dress (even a wedding dress!)

Find your style, play around with patterns, colors, and lengths!  If you can only buy one pair of boots… I suggest a dark whiskey color with some pretty stitching or colorful inlays like these, or these {which are more expensive, but totally what I want for my birthday!!!}, or these.  Whatever you choose, just have fun with it!  Be daring, be bold, and if you do pair boots and a dress tag me on Instagram! I use the hashtag #rachelsboots.  I’d love to see how you rock your look!

If you have other questions, leave them in the comments or hit me up on Twitter!  I’d love to answer them, and hear how you wear your boots and dresses, or help you figure out how to pair them!

Thank you so much to Country Outfitter for sponsoring this post, and providing me with compensation, and a new pair of boots! All images are iphone images taken by me, and all thoughts and opinions are 100% my own! This post does not contain affiliate links, nor do I get anything if you buy boots from any of the above links.


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  1. Laura in Texas says

    Amen sister! :-) I love wearing my boots and just about anything goes. You have such pretty boots whereas most of mine are workhorses or solid colors but matchable with everything. Have a great day, LAURA

  2. Deb Hardy says

    Be careful with that invitation…i may just take you up on that offer!

    I love my Justin Gypsies. They were really inexpensive but they fit well and they fit my calf (I am still waiting for the day that tall boots fit me).

    You’re boots are awesome and you should meet my friend Bobbi. That girl has more boots than I do nail polish. Many are covered in farm grime but some are fancy and I envy them!

      • says

        That made me laugh so hard! I cannot tell you the number of times autocorrect has been anything BUT correct 😉 <3 ya I haven’t tried the Justin Gypsies, but I’ve heard great things about them!

        Sounds like your friend Bobbi and I should be connected 😉

  3. says

    Love all your boots! I can’t believe I’ve been in Houston for over 10 years and STILL haven’t bought my first pair of boots yet – I’m ashamed. Your boots look so good with all the dresses. This will have to be my year to purchase a pair, I think.

  4. says

    I don’t own any boots… Might be an excuse to come visit you. As soon as I saw those flower boots I fell in love! I want them. They are so pretty! I have such a hard time with trying on regular boots because I have a wide foot and large calf and most boots don’t fit me.

    • says

      Aren’t those flower boots AMAZING! I have been drooling over them for a couple years. Girl.. we will go shopping and FIND the boots for you! They are out there.

  5. says

    Two bits: 1) OMG that is the most adorable photo ever of you! (all of them but specifically, the one of you as a kiddo) and 2) We wear boots only in the winter here. So that it’s a year ’round dress sort of gig there? Love. LOVE. love.

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