Prom Dresses for Small Bust: Stylist Approved Gowns Style Tips on How to Wear a Backless Dress HubPages 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 How to wear a backless dress with a bra!, You guys asked so I finally did a video. This only works when youre wearing a bra your size and is one of great quality. This is your sign to go get fitted!, 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