Fashion Risk...Do or Don't? Discuss

So...I have tried this booties with skinny jeans thing before. It has always resulted in my immediately taking off the booties and saying to myself "What were you thinking? That looked terrible!" :) SO...not sure what came over me on this random Wednesday morning that made me want to , ONCE AGAIN, give this another shot. I didn't even have a plan B. Maybe the fashion gods aligned for me this morning and I was finally going to make this look work!...and for once...I didn't immediately take the shoes off and think "Why did you EVEN buy those??" :) This may not be drastic to you all, but I am excited to say that I THINK I finally made this work? Those gray jeans...Gap...Clearance...10 bucks! I was so proud of myself! I have been SEARCHING high and low for cute gray jeans...and then there they were! Maybe the fashion gods were at the Gap with me too and they KNEW that this outfit was coming! Anyway...Do or Don't, discuss?? :)

Also as a side note...I think I'm going to be working on getting better camera...my birthday and Christmas are just around the corner. I think it's time.