I've often felt like I have to choose between ease and comfort and looking nice. If I thought I could pull it off, I'd wear my nicest clothes every day. The reason I don't? There are a couple.
The first is that not all of them are practical. Canoeing and portaging in a muddy river while wearing a long skirt? Not really possible or practical. I've played soccer in a short skort and ballet flats, and while it is possible, I wouldn't recommend it.
The second issue is that I often feel like I stick out if I wear nicer clothes. If, for example, I wear a skirt to the youth group I regularly attend, I stick out. A couple of girls wear skirts occasionally, but they're usually much shorter than the ones I wear. I also tend to prefer dresses to skirts, and somehow a dress tends to look nicer than a skirt.
The third issue, and I think the major one, is comfort and ease. Let's face it, if you wake up late and you have a lot of work to do, I would bet your first thought isn't Hmm, let's see what awesome outfit I can pull together. If you're anything like me, it's Hmm, where's a pair of jeans and a sweatshirt? I hear that this problem can be avoided somewhat by laying out tomorrow's clothes before you go to bed, but I never remember to actually do that. My love of dresses actually helps me out a bit here--it's much easier to pull on a dress than to find a skirt and shirt that match in both color and style.
I think the way to fix this problem is to go gradually. It's not like I want to be dressed drastically nicely. I'd just like to be a step up from jeans and a T-shirt. I've started buying and making nicer clothes. T-shirts from the craft store are cheap, yes, but they're not good quality, they're not very flattering on me, and they don't look very nice. I am also planning to make a few knit dresses, so I'll be able to pull one over my head and run to class or wherever. If most of my clothes are nice, it's harder to wear something not-nice.
I also wore some nicer clothes last week, to see if I did, in fact, stick out. If I did, no one mentioned it. In fact, the only comments I got on my clothing were two compliments (on different days and different dresses). This makes me feel much more confident about wearing nicer clothes. I think I pay much more attention to myself than other people do. :P
As far as practicality goes, I think I use that mostly as a cop-out, honestly. It's not like I'm likely to need to take a canoe trip without warning. Most things I do can be done in skirts easily, or with a very little practice. The only things that come to mind that you really can't do properly or safely in a skirt are heavy construction and the aforementioned canoe trip. Some things, like bike riding, are harder, but still not that difficult--the key is to wear a wide skirt and make sure you're sitting on the back of the skirt so it doesn't drag on the wheel.
(Please, let me add here that I don't think wearing jeans and a T-shirt is sloppy or lazy. I feel not-at-my-best when I wear that kind of clothes, and I tend to dress down when I'm feeling lazy. That's why I would like to dress more nicely. This post and the comments about clothes in it apply to me. I do not think the less of you if you wear jeans and T-shirts and sweatshirts.)
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