Boots -Story Work Chelsea Snug and smart, a great pair of Chelsea boots are both versatile and functional. Ankle-skimming, these booties have been icons since they first surfaced in the 1960s. Wear with: A sweater and pleated skirt. Wedge Wedge heels afford the glamour of stilettoes without making you stumble over. When teamed with your go-to work outfit, they let you power pace around the conference room. Wear with: A fitted blazer and cigarette pants.   Play Thigh/Knee Highs With Nancy Sinatra and Julia Roberts as ambassadors, over-the-knee boots win our seal of approval. Wear with: A mini skirt, sequinned dress or even a pair of skinny jeans. Lita When shoe brand Jeffrey Campbell unveiled these in 2010, a star was instantly born. Named after Lita Ford, lead guitarist of ’70s rock band, The Runaways, these vertiginous boots always manage to grab eyeballs. Wear with: A biker jacket and glittery mini. Chill Dr Martens The original combat boots, Dr Martens appeal to the souls and soles of cool girls, ’90s kids, grunge folks, and street style stars. Identifiable by their distinct high-top design, stitching details and unique air soles, they are the most comfortable pair of shoes you can own. Wear with: Everything in your closet. Uggs These fleece-lined boots have divided the sartorial world. Fashioned after sheepskin boots worn by Australian surfers in the ’60s and ’70s, Uggs blazed into popularity a couple of decades back and continue to reign supreme. Wear with: Jeans, joggers or sweats. Cover image courtesy Shutterstock, illustrations by Aditi Sharma