Please commentate on my fashion (or lack thereof) commentating

I fell in love with these boots last week:

My husband, who has fantasies of me being a full-time cowgirl, was happy to oblige my every (cowgirl) desire.

Because of that happiness to oblige....I ended up with this too:

But now......you see, I have boots. And a belt. But I do not know what else to add to that cowgirl equation.






I am used to boots like these:







Well, they are black like these, but more of a croc skin type of patent leather.

Yes. Croc skin patent leather.


Weird. I know. But with BLACK, I know how to dress. I have BLACK down.


But brown.... well, brown has other issues. The other pair of boots I have are what I would call an Amber color. But Amber, really? What do you wear with Amber boots? I wore a big orange sweatshirt and went to MFA, or on a buggy ride, where no one really cared.


Maybe I am the one with issues.

I found that I had three dilemmas with the boots.

1. I have ONE pair of jeans that fit and they are intended for flip flops. Since losing some weight, I am currently down to one pair of jeans. This is because approx. a month before starting my diet, I gave up on ever losing weight and gave away all my jeans. Ahem. Now it is closing in on fall...which is also when I start wearing jeans with heels and I am going to need some jeans with some length. Jeans that don't currently have a pony tail holder looped strategically around the loop, back to the button, back to the other loop and back around the button. Yeah. I am cool like that.
2. My second dilemma, that I discovered when trying on with aforementioned "flip flop" jeans, is that I have an issue with dark wash jeans with lighter colored shoes. Who knew? Although the leather is not light....it isn't black (which we have established I know how to work with), and the darker wash jeans seem to stop and point to the boots and say....."Look! Here are her boots!" (Of course that could be because they DID stop...right about my ankles.) I need some cohesiveness...some unity..mind you, in my outfit.
3. My final dilemma is that I also noticed when trying on with "flip flop" jeans that you could see where the top of my boots were under my jeans. Maybe this was because of the short length and absence of "bulk"....? Or maybe it was because someone 5'2" wasn't meant to wear tall topped boots? I so hope this isn't the case.
4. Since I was never very good with numbers I will add another dilemma....a 4th, what have you, on a list of 3. I feel that I should address the suggestion of "tucking jeans in" and "wearing with a dress" before they are actually made. I haven't ruled out the possiblity of wearing the jeans with a cute dress. However, since I have a weird body, the probability of me finding a dress that fit right, without making my hips look 3x bigger than normal, is slim. If I do, I will most definitely try the dress on with the boots. Also, I am not opposed to tucking the "britches legs" into the boots....if it is accompanied by a sweatshirt that also conveys the "'Oh, I just threw a shirt on and pulled my boots on and was in too much of a hurry to think much about my outfit' look" that is essential to pulling it all together...or a oversized shirt with some skinny jeans that says "I am not afraid of bulk on top to balance the obvious bulk on bottom".

You can see that I am in an obvious quandry. I only have one shirt that is brown and plaid (to be worn over a brown tank top -with or without the belt) and no jeans.
I think that jeans might be an essential part of this equation, barring the finding a miracle dress.
Any and all help -or links -would be appreciated!