However, I've always cared more about the outfit excluding the shoe. This, in some cases when I look back at old or even rather more recent photographs, can be the ultimate mistake which I've been making for years. 

Shoes pull an outfit together, like sewing the seams of cuts of material together to make one garment. They are as important as those little stitches. 

I'm a big converse fan; wearability, fashion, comfort all in one. And usually, they go with everything. But then there are outfits that they do not go with...as with any time of trainer shoe.

I also own a LOT of boots; about five or six at least. These also go wth pretty much everything.

But my shoes are so boyish. None of them are very pretty or girly. I remember when I was a little girl and my dad would polish my school shoes for me everyday so that I looked "smart". But I would complain that "no one even looks at your shoes". To which he would reply "yes, they do".

And he's a million percent right; they do. Women often even judge a man's attractiveness and appearance on their shoes. How this works I don't know...except maybe... Trainers = chav = bad boy = attractive = tempting = probably not the best idea. Or pointy smart leathers = business man = money = lets go become a goldigga.