Photo: Jonathon Kambouris

1 of 25
Old School: Comfort shoes are ugly.

New Rule: With so many fashionable options out there, comfort no longer means frumpy. These triangle-heel sling-backs by former engineer and ballroom dancer Anyi Lu are not only sleek—they also have a cushy insole, a deep extended toe box and arch support. Cha-cha-cha!
$425; AnyiLu.com.