know what style of shoes.? Pictures would be helpful.
http://www.forever21.com/product.asp?catalog%5Fname=FOREVER21&category%5Fname=top%5Fdressy&product%5Fid=2080734923&Page=all&pgcount=25
no to jeggings, yes to leggings. you could also try a kind of black pencil skirt underneath for a smarter and more sophisticated look.
I reckon some black slingback wedges would work well. Like one of these:
1)http://cgi.ebay.co.uk/NEW-LADIES-BLACK-SEXY-SLING-BACK-WEDGES-BOOTS-SIZES-3-8_W0QQitemZ140407338557QQcmdZViewItem?rvr_id=&rvr_id=&cguid=f3eb27641280a0e201b23e12ffc8c350
2)http://www.marksandspencer.com/Limited-Collection-Slingback-Wedge-Shoes/dp/B0038FTBCW?ie=UTF8&extid=TP_2_FRO_T_MSF_
3)http://www.johnlewis.com/101364/Style.aspx