I don't know about you, (the person currently reading this), but I hate doing things just because someone told me I have to. I like doing things when I understand them, I'm passionate about them, and want to do them. Being Jewish doesn't always allow one to do things because of those reasons. Often, we're doing things simply because we were told we should, we had to, or there isn't a different way to do it. I mean think about it, a lot of the Mitzvoth in the Torah we do simply because we grew up being told to do them.
If I listed you all of the Mitvoth I actively do, most of them would be just because I do them. I honestly wouldn't be able to give you an answer, it just makes sense so I do it. However, when it comes to dressing Tznious I find it very hard to just do it. I can't just always wear tights because I'm told it's more Tznious. I can't wear my skirt at the same length everyday. I can't measure with my fist where my shirt sits on my arms and collar bone. Measurements with regard to how I dress, besides for the process of making clothing, doesn't sit well with me.
Tznious was always very confusing to me because of the measurements. There are SO many interpretations of what is considered Tznious, it makes my head spin. One day I will think I am perfectly covered to Tznious standards and suddenly someone will be like "You aren't Tznious. You're wearing red." I mean for the love of god, can we at least leave colors out of it? I used to hate wearing red because I had red hair. I would avoid red and pink always. In Seminary I began to love the color on me. I bought a few clothing items that were red for shabbos and suddenly people treated me like I belonged in the red light district instead of Shul.
I felt so uncomfortable with the way people stared at me and shunned me. However, I chose to not care. I express myself through my clothing. If I only wore dull, dark colors all the time, I would feel dull and dark. I wear bright colors, crazy prints and sometimes even dare to wear clothing that flatters my body shape. I also dress modestly while doing this. I have never been the type to show off my body. I had a short time period in my life (end of middle school until 10th grade) where my self esteem dropped so the length of everything I wore shortened like crazy. I thankfully realized I wasn't comfortable dressing that way either. I wanted guys to like me, but I didn't want to be liked for my body. I found comfortable boundaries for myself which also allowed people to get to know ME.
The length of my dresses, sleeve lengths, where shirts sit on my collar bone all vary. It varies because sometimes I feel the need to adjust the boundaries I've made. When I got married I felt the need to cover more. For me that meant making sure I wore a tank top under a button down shirt, a slip under dresses/skirts just in case they are see through, and not to wear really fitted clothing if I'm not with my husband.
I personally find nothing wrong with wearing fitted clothing. The difference one must recognize is there is fitted and skin tight. I always try to avoid skin tight, but I don't think fitted clothing and modesty contradict themselves.
I'm not here to say dressing Tznious is bad and you shouldn't do it. It's wonderful, and everything in the Torah is there for a reason. I haven't yet found my connection to the measurements, so I do my best with dressing modestly. If you are able to dress Tznious, do it!! Rock it!! Own it!! For anyone struggling with it, like myself, know it's okay for your level of modesty/Tznious to vary. There is nothing wrong with you, and it's very normal because it's a STRUGGLE for you. If you fall one day, get back up and try again. It's not a hit or miss opportunity. Every single day is a new day for you to try again.