We had an interesting string of posts on 'butt-ugly' shoes a while back - you may want to do a search. I think it was rather amusing and may help keep this in perspective.
I not only wear my Birks with business skirts - I wear Birks _AND_ big fat socks and business skirts. I need the padding on my feet. Yes, I look ridiculous -it certainly keeps me humble. And reasonably comfortable.
I have started to change my wardrobe (as my budget permits) to go with my ugly shoes. Most people match their shoes to their clothes - not me. I look at an outfit and say 'Yes, it's cute - but how will it look with the Birks'. I wear a lot more trendy/casual 'GAP' type clothes - so the shoes don't stick out quite as much now.
Hope you find something that works for you.