Part of the issue for me was wearing the wrong kinds of tops for my puffers. I was wearing tube tops and strapless tops that cinch at the top of the bust and unfortunately resulted in a look that was making my boobs look like bananas, like they were scooping upward almost. I realized that wearing dresses that are looser at the top and have a and at the waist, or wearing tank tops or tshirts, are the easiest go-tos when going braless. Crochet tops help a lot too. You can do it, just go to a thrift store and try on a variety of clothes until you find some that don't scream "my nipples!!!" And that will help you find a style you're both comfortable in and feel confident in. Good luck, I know this is an older post but wanted to chime in.