Most of the women wearing the most extreme forms of covering are doing so in response to it being the local costume. Their particular level of piety may or may not be reflected-or even their family religious inclinations or political ideas being liberal or conservative. If you live in Saudi, you dress as a Saudi. I can visit Saudi and as long as I'm modest, no one will say boo. Few countries have legislated this, but going against local custom can get local ones burdened with assumptions about their modest character. My family lost their minds when I covered, still wearing western clothes, just the modest version. They Aren't religious or politically extreme people mostly, but I was going against our culture. Freaked out all my family. Many let me know that they didn't care what I felt, but I was disrespectful of "our way of life" by covering my hair in a way that looked Muslim. Strangers mostly don't comment or respond, but family does. (Some traffic issues in Tx being big exception)
My friends religious and pious family objected when she started wearing a simple headcovering, and they lived in the Levant. I have a friend who is questioning EVERYTHING and her family knows and is supportive of her quest. She wears hijab out of respect and everyone knows she is toying with every faith and non faith system. This has no threat attached-her dad is cool. She was raised that way but she will likely not wear it if she chooses something else, but that is her slightly different take on it. Her comfort level is her own.
Don't presume. As a new Muslim I have done that myself. Most are not doing it as subservience or force. Some must be, but I think most non-Muslims make a lot of assumptions based on their own beliefs and culture. I know Muslims do the exact same thing. The basic foundation behind women covering in Islam is modesty, not subservience. When Muslims from covered cultures see very uncovered women, they assume immodesty. You see women covered and think it's about subservience. It just isn't. Not at its source.
Muslims growing up in the west are more likely to choose based on a religious understanding, but an uncovered Muslim is not necessarily liberal or conservative in general. It's a personal decision. Their own religious understanding. Or just preference or need. My family means right now I don't have freedom TO cover. But knowing, they still give me hell no matter what I do.