Van der Weyden-an example of a chaperon in the mid 1400s
"In France in the 1600’s, when Perrault wrote his version, titled "Le Petit Chaperon Rouge," a chaperon was worn by women of aristocracy and middle class. Thus for a village girl like Little Red Riding Hood to wear a "red chaperon" made her a nonconformist. Clothing codes were strictly enforced during Perrault’s time. Thus the wearing of the red cap is one way that Perrault sets up Little Red Riding Hood as not doing what one should. It also contributes to why she is punished in the end." -From Annotations for Little Red Riding Hood, this note from Jack Zipes
This note, which I've read before, seems to contradict this from wikipedia:
"By about 1480 the chaperon was ceasing to be fashionable, but continued to be worn. The size of the bourrelet was reduced, and the patte undecorated. St Joseph could, by this stage, often be seen with the evolved form. By 1500 the evolved chaperon was definitely outmoded in Northern Europe, but the original hood form still remained a useful headgear for shepherds and peasants. By this time the evolved chaperon had become fixed in some forms of civilian uniforms for lawyers, academics and the members of some knightly orders. In these uses it gradually shrank in size and often became permanently attached to the clothing underneath, effectively just as an ornament. In Italy it remained more current, more as a dignified form of headgear for older men, until about the 1520s."
So, was Perrault's story supposed to have been set years before? In that case, red chaperons were sometimes even used to denote political affiliations. Although, the wikipedia article doesn't talk much about the chaperons as worn by women or children. I've tried doing a little digging into more of the history of fashion of the era and haven't found anything to support Zipes' statement but I hope to look into this further (please let me know in the comments if you have sources or knowledge of this topic!)
Anyway, the little girl who encounters a wolf is now famously known to English speakers as having worn a red cape with a hood, through translation differences and multiple illustrations. I had mentioned a while back that it's common for modern interpretations of LRRH to wear a red hoodie, since capes aren't typically worn any more. However, I've read that for the fashionable crowd, capes are coming back as a trend for this fall/winter season. So if you want to dress in a way that's indicative of the famous character, now would be a good time to snatch up a red cape! I personally like the versions with the faux fur around the hood, as a further tie in to the story (and Little Red's ultimate triumph over the wolf-at least in certain versions...)
Monroe and Main $39.95
Also, if you're interested in modern fashionable interpretations of Little Red Riding Hood, style blogger The Clothes Horse has a post of inspiration pictures, including this wonderful collage: