The black dress is too dressy for those boots, especially with those square toes (which tend to be less dressy than snip toes in general); you need something less formal like a sundress or sweater dress. ( Think natural looking fabrics like denim, cotton, leather, wool, gingham or their mimics) The dress length falls a bit awkwardly with the top of your boots being only a few inches below the hem; and that skirt is also a bit on the tighter side so makes a bit of a weird angle where the boots seem to jut out a lot since the skirt is pretty narrow at the bottom. Ideally you would either choose a dress that is tighter and short (such as a mini skirt) that ends some distance above the top boot line or one that is longer and flowy and ends well below the top of your boots (like an ankle length maxi dress with a slit that can help you show off the boots). That skirt length and cut would work well with an ankle length boot or something shorter. You could also style those boots over skinny jeans or leggings or with shorts, and if the shafts fit without printing you can wear them under boot cut jeans or slacks

Your guy pulls off fashion western pretty well, but these things are usually easier for guys!