A couple of years back I was hosting two female Russian acquaintances in Helsinki. As I got up one morning to go to Uspensky Cathedral, they expressed interest in the Finnish Orthodox Church and felt bad that they had not been to a liturgy in a few years and were losing touch with Orthodoxy. But when I suggested they come along, they said, "Oh, we can't! We didn't pack any skirts." All their lives to that date they had watched babushkas chastise women for trying to enter a church wearing pants. Having been to their hometown regularly, I know this crowd, and the thing is, the priests generally don't mind if women wear pants, but it's the old women at the door who decide who gets to enter and who doesn't.
In the end, I just couldn't convince them that in the Finnish Orthodox Church, you won't see too many women wearing skirts, and there's no pressure on dressing in just the right way. Nonetheless, they were too afraid to come along with me. If rules on clothing are frightening willing Christians from coming to church and rededicating themselves to Christ, then a gentle push to "modesty" has gone too far.
FWIW, in the Romanian Orthodox Church, pants are fine in parish churches, and at monasteries it might be best you wear a skirt, but the monks and nuns are always thrilled to get visitors anyway and you'll always be welcome.