Indeed, from as early as before the year 1000, images in the Western world had acquired the habit of reserving a pejorative status for striped clothing. The first figures who are graced with them –at first, in illuminations, then in mural paintings, and later on in other media– are biblical figures: Cain, Delilah, Saul, Salome, Judas. Like red hair, striped clothes constitute the usual attribute of the traitor in the Scriptures. Of course, just as they are not always redheads, Cain and Judas, for example, are not always in stripes; but they are so clothed more frequently than all other biblical figures, and those stripes, when present, are enough to reveal their treacherous characters.
Beginning from the mid-thirteenth century, the list of “bad” characters dressed in such a way grows considerable, notably in the secular miniature. […] In the image as in the street, all those outside the social order are often marked in this way by striped attribute or piece of clothing, whether because of a condemnation (forgers, counterfeiters, traitors, criminals) or because of an infirmity (lepers, hypocrites, the simple-minded, the insane), whether because they are employed in an inferior occupation (valets, servants) or an ignominious trade (jugglers, prostitutes, hangmen, to which the image often adds three contemptible tradesmen: the blacksmiths, who are the sorcerers, the butchers, who are the bloodthirsty ones, and the millers, who are the stockpilers and the tight-fisted ones) or because they are no longer Christian (Muslims, Jews, heretics). All these individuals transgress the social order, like the stripe transgresses the chromatic order and the order of dress.
— Michel Pastoureau, The Devil’s Cloth: A History of Stripes and Striped Fabrics, New York: Columbia University Press, 1991, this passage cited in Implicasphere: An Itinerary of Meandering Thought, an occasional publication edited by Cathy Haynes and Sally O’Reilly. This edition is called “Stripes,” London, 2007.
The visual embodied humiliation of inmates as public punishment has returned in the first decade of the twenty-first century…. The return of the overtly visible nineteenth-century black-and-white stripes as embodiment of punishment takes on an even more stigmatized meaning it did originally. Comic representations of the iconic uniform in film have meant that audiences have questioned this type of visible embodied punishment. Yet, Right-wing prison authorities depend precisely on these historical associations in order to make inmates ridiculous to the outside world. Shaming instead of rehabilitation is embodied in the return of the iconic black-and-white stripes.
–Juliet Ash, Dress Behind Bars: Prison Clothing As Criminality, London: I.B. Tauris, 2010, p. 155.
threadbared 
Stripes also have been appropriated recently by various subcultural arts movements oriented around circus and vaudeville. Lucent Dossier, Vagabond Opera, Vau de Vire Society, among others frequently wear black-and-white stripes as part of their look.
I recently stumbled upon your blog and have been thoroughly enjoying it. Thanks so much for sharing your thoughts.
If they push the striped for convicts enough, it could spring another fashion trend much like the oversized ‘gang’ styles, tattoos, and shaved heads that have come out of prison attire in the past few decades.
p.s. to the above comment: I can’t help but notice the striped tights worn with goth and steam punk, and how knit stripes are back again in the current preppy revival for sailor’s striped knit shirts, now being adopted by menswear as well as women’s.
From a cultural standpoint, isn’t it interesting that stripes, required a more difficult time warping the loom, and therefore more labor intensive (so potentially more desirable) would be awarded to ‘less deserving’ outcasts?
The pre-Code film Hell’s Highway (1932) portrayed the inhumane treatment of prisoners; among other more predictable forms of punishment, inmates had to wear uniforms with (striped) bullseyes on their backs that not only drew attention to their prisoner status, but seemed to invite/encourage actual gunshots taken at them, dehumanizing them even further.