Sometimes, head-covering isn't as easy, or even as possible, as it's been for me. Here is one woman's story about her love and hate relationship with covering her hair.
She talks about a few different problems. I'm going to share my read of her issues, and then my own thoughts about them.
1. We pressure people into doing things the same way, regardless of how things work for different people.
I agree. There are a lot of different ways to practice Judaism, and even a lot of ways to practice and be Orthodox. The fact that our communities tend to push for uniformity is a social problem, though, not one having to do, specifically, with head covering. It's also about tznius in general, and where we send our kids to school, and to camp, and how often we go to Israel, and a Ton of other things that really bother me about the Jewish community.
2. It's hard to cover your head, because the things tilt and slide and get uncomfortable.
I haven't found it that hard, but I had the head start of wearing assorted partial-head coverings (kippot, headbands, smaller scarves) for years before I got married. It's something that I really value. It also made adjusting to a fuller covering, and keeping one on, a lot easier. Clips help too, and other folks use velvet headbands and nylon caps, sometimes made from the top of a pair of pantyhose. There are lots of tricks, but, like many mitzvot that are new to you, this one does take some adjusting to. So did putting on tefillin, when I started. So did wearing a tallit. So did managing to hold a lulav, an etrog and a siddur in only two hands.
3. It's expensive- either you're buying lots of scarves and hats, or (even more expensive) you're buying at least one wig, if not more than one.
Like anything, this depends on your budget, and how you feel comfortable shopping. My first scarves were ones my mother and grandmother had had for years and never worn much. I've made my own caps from crochet string and doily patterns (string is about 3.50 for 400 yards, which makes more than one cap, and you can get free patterns online, and adapt a bit). Other scarves have come from Goodwill and similar sources. If you're willing to be flexible, you can do this for not too much money.
Unless, of course, you want, or need, to wear a wig. Then it is absolutely expensive, and difficult to budget, and even more difficult to rationalize, especially if you hold by the rabbis who say that it isn't necessary. But then, most of the rabbis who say that are Sefardim, and generally only Ashkenazim permit wearing wigs, so you can go one way or the other, but probably not both, unless you're willing to do some picking and choosing. You might be. I might be. (Don't tell my husband, he might get his hopes up about getting to eat kitniyot again...)
4. It changes the way you look to the people who know you already, and to yourself.
Sure it does. And that's an adjustment. I recognize that while I was looking forward to getting to cover, not everyone does- nor does every husband/parent/sibling/friend. There's no getting around it. But a lot of things change when you go through life transitions. Maybe it's most important for newlyweds to have a physical marker, while the social adaptation is still catching up. Maybe it isn't worth it if it causes that much discomfort. I don't know.
5. Probably most importantly, headaches.
This is a very good reason not to cover, or to find some less restrictive way of covering. I think there are ways out there, and ways to adjust. But if that doesn't work- there are permissive rulings out there, go out and uncover your head if you get migraines.
6. No one in our grandmothers' generation did it- so why should we put so much pressure on ourselves to cover? If it's really a mitzvah, why didn't our grandmothers think so?
This is a major question of American Jewish sociology. American society was much less accepting of ethnic and religious difference before the 1960s. To quote one of my college professors, Sylvia Barack Fishman, "People realized that if Black was beautiful, then maybe Jewish was mildly attractive". When our grandmothers were getting married, it wasn't acceptable in general society. Orthodox Jewish men didn't wear kippot outside, for the most part. Many, many more observant Jews ate cold dairy in non-kosher restaurants without feeling bad about it. Young Israels had dinner dances with mixed dancing for their members. Not to mention that Hashkamah minyanim started as the way men could go to shabbos davening and still make it to work on time.
On other words, we have religious freedoms in the social realm that our grandparents never dreamed of. There was a lot of pressure Not to look un-American, not to look different. And by the time things changed- well, if you'd already been married for 20 years, and now there was this new freedom- well, that's a long time to have built an image of yourself as a married woman, as an adult, as a mother, even. It isn't one of those lifecycle transition moments. I can see why even in communities where every newly married woman starts covering every inch of hair on her head, her grandmother still comes to shul and puts on a doily, or nothing at all.
7. What about intermediate options?
I am totally with her on this one. I like covering all my hair, but I don't always cover all of it. (For example, here.) I'm still not sure what the halakhic requirement is, or rather, which set of requirements I follow. There are plenty of different ways of looking at head covering, pick the one that works for you.
It ties into that first issue- there's pressure to do it the way that everyone else in your community does, or the way that the people you think are most authentic do, or whatever else is pressing on you. It's one of those precious challenges, and a way to work on your own autonomy.