Poor religious and the religious poor...

Original Habit of St. Francis of Assisi.

"Suppose there should come into your assembly a poor man in shabby clothes..." - James 2
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One of the most shocking things to the friends and relatives of St. Francis of Assisi as it concerned his  conversion was his dramatic divestment of clothing before the Bishop of Assisi and the townsfolk who gathered to witness the father's case against his errant son.  As most people know, Francis removed all of his clothing, renouncing the world and his familial inheritance.  The Bishop covered him with his cloak and later clothed him in the garb of a pilgrim, or penitent.  (The original tunic is shown in the photo above.)
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The original habit of the Franciscans and Poor Clares consisted of the poorest material - exactly what the poor and the peasant of the day would wear, albeit designed after the habit of the pilgrim and monastic.  The poor wore what amounted to little better than rags in some cases.  The ordinary folk wore the meanest garments, the fabric rough and course - hence the religious habit of the mendicants reflected that poverty.
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Later Teresa of Avila went to great lengths laying down the regulations concerning the Discalced Carmelite habit, requiring it to be poor fabric, not extravagantly made - in other words, short cowls, tighter tunics and shorter sleeves, etc.  Likewise subsequent reforms of the Franciscan order focused upon genuine poverty of dress.  As the history of religious life demonstrates, decline and relaxation of religious observance has often been marked by refinement of religious garb and lodging. 
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Contemporaneous reforms of the Franciscans have also specified frugality in clothing and life style, thus we have seen the adaptation of denim, normally associated with the work and everyday clothing of ordinary people, being used for the habits of several new foundations of Franciscans.  Interestingly enough, I know of a diocesan group of friars who changed their habit from the less attractive denim to a dressier, darker grey-heather fabric, similar to men's suiting, adding a scapular and pulled together by a white cord.  All nice and neat and respectable looking...  Their apostolate seems to have evolved into a more polished, professional organization these days as well.  Secure in a nice convent, the brothers impress me as being very much like the older institutionalized branches of the Franciscans.  The irony of which is not easily missed, since I believe this group, not unlike many similar ventures elsewhere, were founded to be a more authentic expression of primitive observance and evangelical poverty.  I digress however.

St. Clare's Habit.

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My point is that eventually the concern for outward appearance and conventional clothing can infect religious life just as much as it does secular life.  I think some of the few groups who have not yet mitigated their observance of poverty would be the Missionaries of Charity and The Franciscans of the Immaculate, as well as a few other communities, not to forget the very 'little ones' of course.  (I know for sure the Missionaries of Charity do not have suits or dress up clothes, nor do they wear western, secular clothes under their habit - I never got that with other groups BTW.)  This may be good news for the poorly dressed individuals, including those who wear denim to Mass.
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Others may disagree with me on this, but I think there are far more important matters to be concerned with while in church or at Mass than what other people are wearing.  Immodest clothing is another matter all together and ought to be addressed by the priest.
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Remember, the mendicants and monastics dressed poorly, imitating the poor Christ while "associating themselves with the lowly" or poor - their clothing was made of the same fabric as the poor they professed to belong to.  So when you see a man dressed poorly in church, maybe he really is poor.  He's obviously religious if he is in church. 
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Photo credit.