I have recently been inspired to change my look from sloppy mom in ill fitting jeans and t shirt to something more a bit more stylish. I'm really struggling with footwear, especially with the new pant shapes. I can wear anything with boot cuts, but now that I have straight leg cords and a pair of skinny black jeans, I'm not really sure what I should wear. To complicate things, I have fussy feet and need comfort shoes. I don't wear shoes without socks, and can't wear ballet flats because my heels are narrow and the front of my feet are wide. I need to be able to walk my daughter to school in them. I recently threw out the ugliest pair of shoes I've ever owned (bought them when I had plantar fasciitis) and replaced them with Dansko Kips (that they are an improvement shows just how bad my last pair was). I also bought a pair of tall black riding boots and some grey asics (onitsuka tigers). I have two pairs of winter boots, and some all weather moc type shoes. I'm thinking I'd like a versatile short boot, something not too warm (don't want to roast indoors) but still suitable for reasonably cleared Minnesota sidewalks. I'd also like something in a 1-2" heel, maybe penny loafers? Or the boot could have a heel? I don't necessarily want to look "fashionable", but I would like to look put together. What should my next footwear purchase(s) be?