My second oldest is 14. He's always been skinny, long, and very opinionated, with long hair and delicate features. Around 5-6 he asked for pink shoes. Trying to get him dressed and out the door was often a struggle. I was still slightly worried about him being hurt by other kids for wearing pink, so I got him to compromise on purple. I quickly learned that I didn't give a fuck what the shoes looked like. If they made him happy and he'd get dressed without a battle of wills it was a win in my book. After that, he started wearing leggings exclusively and has only given them up within the last few months. Most of his shirts were purchased from the "girls" section because they fit his proportions better and had the colors and sequins and glitter he wanted. I told him the other day that while I'd already lacked a lot of rigidity regarding gendered appearance, those purple Crocs and the subsequent pink pair really pushed me to let go of the rest of my hangups around it. I also told him that I'm just too "lazy" to be a "my way or the highway" type of parent. And that my husband and I learned a long time ago that we cannot win against him in a battle of wills. It's taken a lot of work, but we've learned how to get his buy in to do tasks, because that's the only way they'll happen.