I always listen to the great catholic modesty debates with interest. It seems there is a little bit of everything, from those who think modesty is solely a state of mind and doesn't affect clothing choices, to those who believe in ankle length skirts only, and quote padre pio furiously.
After my parents divorced when I was 6, my mom went through a pretty extreme reversion to Catholism. she was a cradle Catholic but had never taken faith very seriously. When she began to practice her faith she moved to a pretty conservative set of beliefs. We also moved to live on the same property as my aunt and uncle (they are the ones who have 11 kids), who were even more conservative. Consequently my siblings and I grew up with very strict modesty guidelines and explanations (mostly my sister and I, since it seems most modesty rules are really just about women).
I didn't pay much attention to the modesty hubbub until I hit puberty. Suddenly I went from a scrawny little kid running around shirtless with my cousins, to having more womanly features (I've always been pretty skinny, but there is still a big difference between flat chest to an A cup). Like many 13 year olds ( or younger, I matured a bit late), I was painfully aware of my body, its new shape, my attitude and feelings towards boys, all that regular stuff that is insanely awkward in the beginning.
Through high school, my mom held very strict standards of modesty for my sister and I. No sleeveless shirts, skirts past the knee, and mainly nothing form fitting. I know she was trying to protect us and help us develop into virtuous women, but I took the modesty line of thinking to heart. I constantly analyzed what I wore, and how it fit my body. I often wished away my womanly curves (as tiny as they were, anything felt like too much with the stringent guidlines). Being a boy looked so much easier to me. Looking like a sexual being, or feeling anything sexual seemed bad to me.
As I went through college, I slowly stopped following my former guidelines to modesty. My mom had lightened up anyway, but I stopped following the rules on my own. At first it was simply because I wanted to be pretty. I was tired of always limiting myself to unflattering clothing. I liked boys, I wanted to marry one someday, so dang it I was going to start attracting them.
When A and I started dating, he often let me know how pretty he thought I was particularly when I wore something a bit girlier (I spent much of my younger years in big t-shirts and baggy jeans). I also began feeling a new freedom to be beautiful and with it a freedom to be more myself. I vividly remember confessing to my sister that I had stopped worrying about modesty. It's not that I think the idea is that bad, but as a naturally self-conscious and scrupulous person, constantly thinking about modesty left me feeling at war with my body.
I know many people feel very committed to a form of modest clothing, and that it's been helpful for them. However, for me I felt it to be a damaging set of inferences. I hope to keep writing about this topic since, as you can probably tell, my thoughts about it are a bit unclear since I am still figuring out how it should all work in my life.
I would love to hear others' thoughts on modesty and how it has affected their lives, so feel free to share!