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

I love cowboy boots with dresses <3

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 a 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 to 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.

Cowboy Boots with Dresses

Cowboy boots with a short sundress and 3/4 sleeve 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 Wear Cowboy Boots with Dresses? 

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. 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. 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!

      1. 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. 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. 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.

    1. 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. 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.

  6. Rachel,

    I am so happy that I stumbled upon your blog post, mainly because I just bought a new pair of cowboy boots, and I have been trying to figure out a way to wear them with dresses.

    Having been an avid boot lover my whole life, I wholeheartedly agree with you when you say that, “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.”

    I’ve always made sure to invest in quality cowboy boots that not only last forever, but go with almost everything. This blog post was the missing ingredient I needed in order to perfect my classic country style. I can’t wait to rock my next outfit with a dress and pair of cowboy boots!

    Needless to say, I will definitely be back to see what you share next!


  7. I know this an older post but I’ve got a date this weekend and contemplated not wearing my boots because I’m living in Minnesota. Well, guess what? I changed my mind after reading this. You can’t take the southern out of a Texas girl. Haha.

  8. Hi – I’m going to a wedding in SD in September. I bought a cute dress that is form fitting straight, just a little above the knee – I love it. My problem with boots is that I have full curvy calves – I fill up a boot. I tried a pair of Shortie boots that hit right below the curve of my calf and I think I really like this better than a taller shaft full of leg with no slack – is this doable? I know its about personal choice but I am my own worse critic – HELP

  9. I have one question…. maybe a few! Lol
    I’m planning on wearing my boots with my dress for my wedding. Not a fancy wedding or a fancy dress. I’m not a fashion expert at all. The dress a smidge above the knee. What do I wear under the boots?? Panty hose, boot socks, or what? I have no clue. And is there any certain way to wear boots with a dress.
    I’ll sure appreciate any advice!
    Thanks so much!

    1. Hey Debbie! YAY! Just above the knee is a perfect length to show off those boots! I usually wear good quality cotton socks, but there are some absolutely adorable boot socks out there that add just a touch of flair over the top of your boots! You do you! <3

  10. Was never brave enough to wear boots & dresses but after reading your how to I am inspired! If I ever re-marry, I’ll be wearing boots with my wedding dress!

  11. Hi Rachel! I have browsed your page in the past but was just randomly hopping around but now when I was trying to look for how to’s, here I found your web site again. The pair of plum colored boots or (is it black ?) at the far right corner of the photo you posted caught my eyes. What brand are they? They are pretty! I love your tips on wearing boots!

    1. Hey girl! Welcome back! They’re a rich almost dark chocolate/mahogony brown with purple and teal stitching. They’re corral and they’re one of my favorite pair! I’ll look into the name/number of them when I get back!

        1. TOTALLY embarrassed! THESE are Old Gringo. I pretty much only buy Corral and Old Gringo and I got them confused.. OOPS! Sorry! They have a number in them, but it didn’t bring up anything in search. Sorry

  12. I desperately need advice asap!!!! I will be getting married in a month, just a simple, small wedding. I found my dress… it’s mid thigh, cream lace. I have two beautiful pair of boots but I want to get your opinion please. The one is tan with deer skull on the outside legs with flowers, the second pair are tan distressed with crosses. Please let me know what you think. Thank you!

  13. Not sure you are still reading these comments but I am going to a wedding in Texas later this month and was thinking of wearing boots with a dress. Do Texans frown on northerners borrowing their style?

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