Craigslist dominates online classifieds like Google dominates search. Yet looks straight out of 1998. Craigslist.org
Whatever your politics, you have to admit it: this site is ugly but effective. Drudgereport.com
Like Craigslist, this site has a distinctly late-20th-century vintage. Users don’t seem to mind. Metafilter.com
See also: Why the Drudge Report is one of the best designed sites on the web