I wear jeans, cut offs, leggings and shorts most of the time all year round, but also wear skirts (not long flappy ones at my age though - too frumpy!) and sometimes dresses summer and winter for certain occasions - bare legs, tights, boots anything and everything! Skirts are around knee length straight (eg denim) or full gathered and fitted from below waist flaring/gathered out from hips - more flattering style! Great compromise though are tunic type tops - I wear lots of these over leggings or skinny jeans of various colours, summer and winter. They are fitted where it matters and loose enough (long enough too) to cover a multitude of sins!
Hurdity x