Invest in a pair that will last pretty much forever, like these Rosalinda boots from British label Dune. They're timeless, so you can wear them with whatever but the slouchy soft leather works particularly well with midi-skirts. Sitting on a block-heel, these are the type of boots we mean when we say "I need a nice pair of boots but for everyday". Safe to say the search is over.
Dune leather boots
Zip fastening
Almond toe, slouchy fit, press-stud detail at the back
Leather upper, leather and synthetic lining, resin sole