Style Tips on How to Wear a Backless Dress HubPages I love backless dresses but I've been so shy about wearing them. Why? My small boobs. These dresses don't need a bra and if I go without wearing bra Let's not talk I love backless dresses but I've been so shy about wearing them. Why? My small boobs. These dresses don't need a bra and if I go without wearing bra Let's not talk Me and backless dresses are like this I always struggle with what bra to wear though. What do people usually do? Backless bras weren't low enough for this design. So I Prom Dresses for Small Bust: Stylist Approved Gowns