These classy size 9 vintage black patent heels are from the 1960's and still in excellent condition. The uppers aren't made out of actual leather, but they definitely look like it. OldBaltimoreVintage is selling the shoes on Etsy for $30. See the listing for more details, including measurements: http://www.etsy.com/view_listing.php?listing_id=28847889.
These basic black pointy toe flats from the 1980's will go with just about anything. They're labeled size 7.5 (Women's)/Euro size 38, and available here for $14: http://www.etsy.com/view_listing.php?listing_id=28970770.
These 1980's vintage black suede ankle booties look really comfortable. I'm definitely a fan of the zippers and brass buckles. The booties are size 7 (Women's) and are available here for $32: http://www.etsy.com/view_listing.php?listing_id=27591283.
I adore these 1980's vintage Nine West brown leather lace-up boots with stacked heels and gold metal eyelets. They're labeled Women's size 8.5/Euro 38.5 and available here for $28: http://www.etsy.com/view_listing.php?listing_id=28573243.