It doesn’t get much edgier/borderline tacky than leather thigh high boots. But that’s where you’ll find me a lot of the time- tottering that fine line between fashunnn and tacky. There’s so many rules to be broken and so much fun to be had there.
A simple styling trick to make leather thigh high boots more wearable is to dress more modestly up top and play with texture- try suede, velvet or corduroy. It also makes a world of difference when the dress or skirt ends lower than where the boots begin and you don’t have that bit of skin peeking out above the boots.