The long answer: I attended my first extraordinary form Mass in January of 2008, with my head brazenly uncovered. (An experience I recount in this post, which also bears the distinction of being the post that made my mother realize I was in love with Scott. [I was still in denial.])
Over the course of 2008, I attended a few more EF Masses and started to feel self-conscious about my bare head.
I began to ponder the matter and decided that it's the same Jesus at every Mass, so if I was going to cover my head at EF Masses I would have to go all the way and cover my head every time I went to Mass.
That scared me off the idea, plus Scott left Franciscan so I stopped going to the EF because I prefer 8:30 a.m. to 4 p.m. on Sundays.
But the idea wouldn't entirely leave my head. I don't like to say that I ever hear God speak to me, but He did over the course of 2009--little nudges now and then: Why don't you get a chapel veil? - Because I'll look WEIRD. And people will STARE at me! - Okay, then don't. I won't force you.
That conversation happened with increasing frequency as the year went on. Finally I decided to ask for a chapel veil for my birthday/Christmas. Around that time, I saw a post by Hallie Lord on Faith & Family Live about Garlands of Grace. My chapel veil seems to be discontinued now, but it looks like this:
It is hard to take a picture of your own head.
It was out of stock or something when my mother ordered it for me for Christmas, so I didn't end up getting it until the beginning of February. Interestingly enough, my fears of looking weird were allayed due to the fact that two of my household sisters independently started covering their heads the same week I did. (One of them graduated in May; the other one is now my roommate.) I got my veil in the mail on the Monday before Ash Wednesday and wore it when I went to household Mass the next morning.
In the last 13-ish months, there have been maybe half a dozen occasions when I haven't worn it. I wear it at Franciscan, where there are maybe 10 girls with chapel veils. I wear it to my home parish where I am the only companion of a very nice middle-aged lady who has been steadfastly wearing one for at least the last 7 years. I do not wear my chapel veil when I go to certain other parishes--some places, I feel like I'm being radical enough receiving Communion on the tongue. Sometimes I just accidentally forget to bring it.
On the advice of Mari, my EF guru, I wear my chapel veil to Confession, adoration, and any other circumstance where I anticipate encountering Jesus in the Eucharist. (Which means that sometimes I do indeed wear it to Eucharistic FOPs.)
There are a half-dozen reasons I can give for why I think it's a good thing to wear a veil at Mass. When you're a distractible person like me, putting the veil on is a tangible way of saying to yourself, "Hey! Entering CHURCH! Pay attention!" It makes me less vain about my frizzy hair, since it's all just getting smooshed under the veil anyway. It makes me take care to dress more nicely and femininely altogether. (I have heard from several sources that jeans and a chapel veil look weird. I don't know about that; I just know that I feel more dressed-up wearing the veil and that comes out in the rest of my outfit.)
But that's not really the why for me. Nor is it because I want particularly to get in touch with 2000 years of tradition, nor because I like the theology of the veil, though those are all good reasons.
As illogical as it sounds, I did it because and only because I was asked to do it.