Dear Sister Laurel, I read the following quotation from Thomas Merton which I thought was terrific. I wondered what you would say about it since you wear both cowl and other monastic garb. Would you mind commenting on it? I guess I also wonder if you agree or disagree with Merton's practice. [[I am deliberately discarding everything that can conjure up the artificial image of the monk in a cowl, dwelling in a medieval cloister. In this way I intend obviously, not to disparage or to reject the monastic institution, but to set aside all its accidentals and externals, so that they will not interfere with my view of what seems to me to be deepest and most essential.]] Thomas Merton, "Notes on a philosophy of solitude," Disputed Questions.
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Thus Merton's comments, when read in this specific context were not contributions to a discussion of whether or not one should wear a habit and/or cowl. Instead Merton wanted to examine the essence of a call to solitude where the individual lives the most basic or essential existential isolation and loneliness common not only to every person but to God as well. More, he wanted to do so in a way which demonstrated its enormous and universal challenge and meaningfulness. To do this he did indeed eschew those things which are "accidentals" or mere externals and which pull the discussion in the direction of monastic life alone so that he might also include folks like Thoreau. Solitude as Merton portrayed it, is a fundamental existential characteristic of human and Divine life. To embrace it as vocation is to serve both God and Mankind in a radically significant way. So Merton stripped his discussion of artificial elements which would only speak to and of a monk in his cowl or a Medieval cloister.

If you notice Merton's own practice you will see that he wore a habit at times and ordinary monastic work clothes at other times. I don't think he rejected monastic garb, nor do I think he was all that concerned with what he wore --- and this would include not eschewing the Trappist habit as something external as much as it might have included embracing it as something which was not merely external. Merton was a Trappist and part of that tradition and life was the Trappist habit. Diocesan hermits today may or may not wear a habit and/or cowl. Those coming to c 603 life from some form of religious (cenobitical) life will tend to wear a habit which is a modification of what they already wore.

Eduard Schillebeeckx, a 20th C. Dominican theologian describes this same process in his essay entitled "Dominican Spirituality" in God Among Us. [[For the most part people live by stories. I myself live by my own story. When I became a Dominican I linked my life story with the family Story of the Dominicans; as a result, my life story took on a new orientation and I picked up the thread of the story of the Order in my own way. So my own life has become part of the Dominican family story: a chapter in it. Through the story of the Order I have attained my own identity. Stories of the Dominican Order keep us together as Dominicans.
Without stories we should lose our memories, fail to find our own place in the present and remain without hope or expectation for the future. Thus as Dominicans we form a group by virtue of being our own storytelling community, which hands down its own traditions within the wider story of the many religious communities, within the all embracing story of the great community of the church, and within the even greater community of humankind. This makes us our own special family, recognizable from all kinds of family characteristics. Some are major, some are minor, but none of them can be hidden.

I understand the wearing of (and often, the well-considered choice to relinquish the habit in certain circumstances) is part of this process of making a particular story one's own and assuming responsibility for being a living chapter in that story. It is only a part of the necessary deepening of an ecclesial vocation such as c 603 eremitical life, but in such a process, when lived well it is certainly more than something which is merely an external and superficial element of living out one's call. For the solitary canonical hermit who must live "stricter separation from the world" in the midst of the world, the habit can be an especially challenging as well as indispensable piece of embracing both the mission and charism of her vocation. Those who choose not to wear a habit (and lay hermits who may not do so anyway because they have not been given the right) embrace characteristics like the call's hiddenness differently and tell the eremitical story in a different way. So long as each hermit is acting in considered and prayerful ways they are an important part of the essence of the call and an expression of the depth such vocations demands.
I hope this helps as a start on this topic of habits.