I think that learning to wear clothes is just part of the growing up process. When I was ordained a priest, I did not feel comfortable in my priest vestments or black suit. Suddenly, I am ordained, but it takes time to grow into the "priesthood" and clothes are a metaphor for that. When I worked in the business world, I never felt comfortable in a suit and tie. My Dad did. He belonged in the business world. He was comfortable there. I was not.
Some people simply do not see themselves in the world of glamour or dress up or business wear. They tend toward clothes in which they feel comfortable. Our comfort clothes will tell us something about who we are and who we are not. To "dress up" for me would be to get out of my comfort zone. I do it when it is appropriate for the occasion, but I feel like I am an actor in a play. When my Dad "dressed up", he was at home in his clothes.
I think that prayer comes in various styles. Some people are at home in "getting all dressed up" and we call this high liturgy. It has lots of pomp and circumstance. In those settings I feel like an actor in a play. I am more comfortable in my monastery where we wear jeans and flannel shirts most of the day, and our liturgies are very simple. I prefer prayer settings of silence and solitude. I don't need to so much to stare at the tabernacle, as to close my eyes and look at no image at all. In this prayer setting we even use terminology such as, "Strip yourself of ego," and "Become naked before God." When you are glamorous, everybody notices you. In contemplative prayer you become anonymous. You disappear into the Divine. It is my style.