How to wear Cowboy Boots with Dresses

This post comes to you as a sequel to Cowboy Boots...A Girls Best Friend, because of it's unexpected popularity and the fact that when I wrote that, it was more about my story with boots and less about how to wear your cowboy boots. It's also because it's summer time, and more and more gals are going to start wondering weather they are brave enough to jump into a pair of boots and a sundress! I'm here to tell you there is a reason why you may be nervous: cowboy boots are bold! The good news is that the sooner you realize this small, but important fact, the closer you will be to making great outfit choices involving your boots.

Now that we've got that out of the way, lets assume for a minute that you don't yet own a pair of boots. 
Which ones to get? 
(Already have a pair? Feel free to skip over this next part to Let's Talk Dresses-my feelings won't be hurt)

With all of the new colors, shapes, heel and shaft heights out there, it can be intimidating. If you are new to boots, and plan on wearing them mostly with dresses let me make just one suggestion...go brown for your first pair, and please for the sake of all things good and right, be sure and buy leather. This is an investment, and the last thing you want to do is strut your stuff in a pair of pleather boots. If that little voice in your head is asking you, "But how will anyone know the difference?" Trust me they will! When leather boots scuff, it shows that this isn't your first rodeo. It says, "Yeah, I'm a girl whose not afraid to get dirty and work hard." Guys like that. Trust me.
When pleather scuffs, well it doesn't really peels. It looks tacky and cheap, and nobody wants to be tacky or cheap.
Okay back to the color. I suggest brown because it is a good staple to have in your closet. Seems silly to start branching out to other colors before you are confident in your trusty brown boots. Also, color adds more boldness to the boot. If you are already a little unsure about this, you'll stand out a little less in brown. Brown also goes with most everything, so it's a 10 in versatility.

Yes, they come in many shapes...toe shapes that is.
Again, my suggestion on shape is considering that you are mostly looking to wear your new or existing boots with dresses. In my opinion, wearing your boots with jeans opens up a world of opportunity that you just don't have with dresses. So for dresses, I suggest a pointy or snip toe.
The point helps elongate the line of the legs and adds a little "dressy factor" that is always a plus when wearing even a casual dress. The other bonus is that pointy or snip toe boots also look great with jeans. Score!
If you must know why I steer clear of round toe when it comes to wearing dresses it's because in the farm world, rounded toe boots say, "working boots". 
Hey did she just contradict herself? 
Didn't she say guys like hard working girls? 
Hold tight, I didn't. Well, I did.  But what I meant was they like a worn-in boot and a girl whose not afraid to get dirty. However, they don't want their elevator eyes to come to a screeching halt when they get to your boots because they can't get past the image of  horse poop, mucking stalls, and feeding livestock. 

Heel and Shaft Height
Heel height is important when it comes to pairing boots with dresses. Think about models on the runway. Even if they are 99.9% nude there is one thing they will always have one. Are you with me? Heels! There is a reason us ladies wear heels and it's because it does good things for our overall look. They extend the leg, lift the tush, and make us look a tad slimmer. 
So when you go to buy your boots, please pass by the ropers! 
On the opposite side of things, I urge you to also be careful of going with too tall of a heel. A super high heel on a boot can scream, well, I hate to say it, but slutty, sleazy, or easy. 
Wow! That was uncomfortable! Sorry, I had to do was for your own good...promise.

Shaft height is pretty standard in cowboy boots. I have noticed this year the short shaft is becoming more popular, but I consider those more of a fashion boot and less of an authentic cowboy boot.
If you are tall, Liberty Boots makes an extended shaft that would look fabulous with sundresses, but for us vertically challenged girls, we'd better stick to the regular height shaft so that we don't end up looking like we are playing dress up in our mama's closet.

Another thing to pay close attention to when trying on a boot is the shaft circumference. Those of us with what I like to call "athletic calves", are going to have a little more trouble here. You want to be careful not to get a boot that fits tightly around your calf. Not only is it uncomfortable, it screams CHUBBY when you wear them with a dress. Again, just being honest here. Don't hate me.
The other plus to getting a boot with a little wiggle room in the shaft is that is provides a convenient place to store your Cowgirl Canteen (super cute hip flask made especially for women).

Okay, so now that we have the boots figured out,
Let's talk dresses.

It's summer time, so I am going to focus on shorter length dresses. 

(For the record: I have worn a maxi dress with boots before, I'm just not sure I'll ever do it again. It probably works better for taller gals, but for me, well, I felt like I already had most of my body covered up with the long dress, and that my feet needed to be free!) 

When choosing a dress to wear with your cowboy boots, think feminine, and flirty. I am going to revert back to the rule we talked about earlier.
Boots. Are. Bold. 
Wearing boots with dresses is already sexy. Getting a super short dress, with cleavage spilling over, or one that looks as if it's been painted on is not going to do anything for your class factor. 

Choose something that shows a little bit of leg (not showing enough will make you look short).
Flowy, non-form fitting look best. 

The idea here is that the concept of wearing your boots with a dress is what is sexy. The attention should be on the outfit. If you want to put emphasis on body parts, then be sure and lotion up your arms and legs so that they are glowing, or opt for a strapless dress. 

Need a cover up option?
A nice denim jacket does the job and looks super cute! 

I hope this helps answer some questions and you feel confident in rocking your boots with dresses. I hear a lot of women say that they despise wearing shorts in the summer time, and this is the perfect solution!

Want more inspiration?