This is our Story: I have issues.....shoe issues

I LOVE shoes. Like most women. I love having a variety of shoes to wear for whatever outfit Im trying to complete or whichever mood I may be feeling. Im in a shoe rut. I desperately need new shoes. The problem is, Im picky. Really picky.
The new styles are starting to grow on me, certain ones are. Certain ones are not. The thing with fashion and styles and the day and age we are in, we are forced to purchase what everyone is "feeling". Its rather amazing when you think about it. The way designers are able to draw us in and the way are taste changes from year to year season to season. Some ways slightly, others drastically. I personally look back at some of the styles I "sported" and think WHOOOOAH why didnt ANYONE tell me?!

When I was pregnant with my daughter my feet grew, sometimes I think a 1/2 size, then there are times where its more like a WHOLE size. At the time it was a huge inconvenience. Nothing I had in my closet fit anymore, and its not like prepregnancy clothes, where you can hold on to them because we KNOW we will be putting them right back on. Huh. We cant put our feet on a diet and the chances of them shrinking back to their prepregnancy cuteness is not going to happen. I do feel that this happens for a reason. This is everyones way of telling us, "You are now a Mom, your styles must change. You must look and act the part." Really Im serious.
So back to my desperation. I need new shoes. New fall/winter shoes. I have a few issues. The first being that Im really picky. Putting that aside.
I want cute tall fall boots. This leads me to the skinny jean factor. They are "In" right now. I swore to myself "I" would not fall victim to the skinny jeans. NOPE. Just not a style that works for me. I dont have sexy long skinny legs with a cute little butt. Since I want these cute tall fall boots, the skinny jeans are growing on me, because that is a style that I like. Some cute jeans tucked into some super cute boots. Now I just hope that I can find some flattering jeans and some boots with wide enough shafts to tuck my calves into while wearing said jeans. Another problem that I have. I have never been able to buy tall boots that zip up, the zipper doesnt make it past my calves. Rather disappointing.

My other issue. I love dressing nice and looking nice and having nice and cute clothes. BUT im a sucker for comfort. I love sweat outfits. I love comfy jeans with tennis shoes and sweatshirts. In the summer I LOVE flip flops. Reef happens to be my favorite brand. So my feet and my legs are not conditioned for heels. I dont wear them enough. Its rather sad. I love a sexy pair of heels but never find myself wearing them. So this leads me to another issue.
Since I love comfort so much I love the little ballet flats (as they are called). BUT I have short legs. Most jeans that I buy stack a little on my shoes because there too long. One of my biggest pet peeves is my pants dragging on the ground. This doesnt work for a short person who has a hard time finding the right length of pants without hemming them. Which I DO NOT do. I know silly right. I just hate spending money on jeans and then have to take them and spend more money to get them hemmed.
So Im stuck with my issues and I really need to get over them. Tennis shoes are no fun in the rain. I KNOW. I spent a whole day at work with frozen little piggies, the shoes may have dried after a while, but the socks stayed wet.