I love boots and have a silly number of pairs. Don't care about looking 'current' and generally wear something if I like it.
Some of my combinations:
Brogue style lace up boots in brown with rolled up straight leg Levi's
Same boots in black, with midi dresses
Heeled knee high boots in tan, with shortish dresses or midi dresses
Flat knee high in black and brown - these don't feel right with much at the moment, but I still like them with skinnies for muddy walks, or with shorter skirts/jumper dresses
Chunky heeled lace up ankle boots, very 90s-esque - with midi dresses or with slim flare jeans
Pixie boots - with mini skirts and tights
Block heeled black suede - these seem to go with just about everything
Beige Ash suede cowboy style - with bootcut jeans or midi dresses
Whistles grey heels - only for taxi nights out, as I can't walk very far in them! They work with rolled up jeans, or bootcut or slim flare, but don't really work with skirts or dresses much, other than pencil skirts
Black heeled ankle boots, slightly platform - these work with just about everything, but too high for every day
I have other pairs but can't remember them off the top of my head.