I used to feel the EXACT same way. Then I saw a picture of a gentleman on here with Kudu chukkas and pleated, cuffed, trousers. Complete home-run; changed my perspective on them forever. I went out and bought two pleated trousers - had my tailor cuff and taper them from the knee down and now I can look wonderful as well.
I also used to think poorly on Chelsea boots...Now they're probably my favorite boot to wear.