Some weeks ago, on a Sunday morning, I happened to look at myself in the mirror and realized that I am quite passably pretty. Honestly, the only reason I was looking in the mirror was because I had a new dress on and wanted to make sure it fit properly. I didn't expect to look pretty in it.
About a year and a half ago I was preparing for the Father Michael Scanlan Scholarship Competition and had quite a time choosing what I wanted to wear to my interview. I didn't want it to be too frilly, but I also didn't want it to look too much like a suit. Finally I found something that was professional but still feminine. Yet I wasn't entirely pleased for the sole reason that when I wore it I looked pretty, and I didn't want to look pretty. It was a scholarship competition, after all. You didn't get points by being pretty, you got points by being smart.
Having a boyfriend has made me rethink my dislike of looking pretty. I think it stemmed mostly from a desire to not look like a "flirt", one of those silly, shallow girls who cares for nothing but looking good and getting male attention. Then Mr. Modest-girls-are-prettier came along and I slowly came to the conclusion that real modesty is a balance.
Think of it this way: If you had a very valuable painting, you wouldn't leave it out on the dining room table to get stained and tattered. But neither would you put it away in a sack where it would get moldy and moth-eaten. You'd put it up in a frame, so that its beauty would be evident but it would still be protected like the treasure that it is.
To dress scantily is immodest because it makes feminine beauty a common thing, to be shared with anyone who passes on the street. Dressing with the goal of covering everything possible is also immodest in its own way, though. It says that feminine beauty is something low and dirty which must be hidden away. Dressing becomingly but without being revealing communicates that I respect the great gift of my feminity.