It's my understanding that oppression or control is not the true religious significance of wearing a headscarf - although if an oppressor wants to oppress he will use whatever tools he can find..
I could try to explain the background, to it all, but it would only be coming from my white westernised non Muslim woman's viewpoint, and some of the nuance, finer points, and context would be lost.
I was similarly curious / conflicted around this issue, I even felt a bit the same, as you did.
So I'd recommend a book called "It's not about the burkqa"
An anthology of writings by Muslim women, who are feminists, oppose patriachal oppression / misinterpretation of the tenets of Islam, but whom also choose to wear a traditional head covering of some sort.
Edited by Mariam Khan.
I'd recommend it.
I guess a close but not altogether parallel analogy might be how I feel about going topless in public.
In some cases and situations I will go shirtless.
In others, where a man might take his top off, I will keep mine on.
This could be said to be down to social, or cultural pressure, or oppression even, because it is the traditional norm.
If I don't keep my top on in certain situations I risk unasked for attention, hostility, lewd remarks or stares, or misinterpretation, of my motives.
As I say it's not a perfect analogy, but just one example of our covering certain parts of our bodies at certain times because we feel more comfortable that way.
There are other precautions I have to take, as a woman, when I go off travelling, and camping by myself for example, which would probably never cross the minds of most guys.
And these precautions, and fears that they are based on, are entirely down to the fact that some men ( not all - but enough) have very little, or no respect for the freedoms and rights of women to go about their lives unmolested.
I hope this helps