I'm not sure I'm going to add anything useful here that anyone else hasn't already said. I was originally thinking you were too hard on yourself until I read your response and I understand about trying to fix outfit duds. I have a hard time with sneakers in general. They generally make me feel frumpy so I have to work really hard on the rest of the outfit to overcome that feeling. I think the length of the cuffed jeans and the sneakers are working against each other. The jeans would be fine in a different outfit with a higher heel.

BTW - I love, love, love your sweatshirt - so perfect for casual wear.