Note: I am not a professional fashion historian. If you spot any inconsistency or outright fallacy somewhere in the picture descriptions please feel free (or even better, obliged) to let me know!
15th century Italy
Bastia Mondovi, Chiesa di San Fiorenzo
Episodes from the Life of St Anthony Abbot (?) (frescoes)
source (flickr, Andrea Carloni)
Always remember to keep your women at a walking stick’s length.
early 15th century (1405-1410), French - Paris
Bibliothèque nationale de France
Latin 7789: De Senectute; Pro Marcello, both by Marcus Tullius Cicero
fol. 56r - “Milo of Croton carrying an ox on his shoulders watching two wrestlers practice in a pen”
http://gallica.bnf.fr/ark:/12148/btv1b84516084/f49.planchecontact.r=francais+7789.langEN
last quarter of the 15th century, French?
BnF
Latin 1173: Heures de Charles d’Angouleme
fol. 3v
http://gallica.bnf.fr/ark:/12148/btv1b8432895r/f1.planchecontact.r=latin+1173.langEN
14th century (ca. 1365), French
University of Chicago Library
MS 1380: Roman de la Rose by Jean de Meun and Guillaume de Lorris
fol. 22v
15th century (ca.1410) France (Paris)
Genève, Bibliothèque de Genève
Ms. fr. 190/1: Des cas des nobles hommes et femmes by Giovanni Boccaccio
fol. 60r - Sardanapalus, among his wives, being informed by a soldier that his enemies are at the gates of Nineveh
14th century (1338-1344), Flemish (Bruges)
Bodleian Library
Bodley 264: Roman d'Alexandre; illuminated by Jehan de Grise
fol. 80v
http://bodley30.bodley.ox.ac.uk:8180/luna/servlet/detail/ODLodl~24~24~141290~145533
14th century (ca. 1365), French
University of Chicago Library
MS 392: Le Jeu des échecs moralisé (The Moralized Game of Chess) by Jacques de Cessoles
end of the 13th century France or Flanders
Lausanne, Bibliothèque Cantonale et Universitaire
U 964: Biblia Porta
fol. 266r
early 15th century (1405-1410), French - Paris
Latin 7789: De Senectute; Pro Marcello, both by Marcus Tullius Cicero
fol. 65v - Lucius Flaminius with his mistress watching an impending execution
http://gallica.bnf.fr/ark:/12148/btv1b84516084/f49.planchecontact.r=francais+7789.langEN
About the incident, from wikipedia:
Cato reported that during his consulship, Flamininus took his mistress with him to the north of Italy. Whilst there, a noble Boii and his family sought sanctuary in Flamininus’ tent. As the mistress had often told Flamininus that she had never seen a man die, the consul turned to her and asked her whether she wanted to see a Gaul die. The Boii noble was still speaking through an interpreter when Flamininus ordered his lictor to behead the Boii noble.
15th century (first quarter?) France?
Paris, Bibliothèque nationale de France
Français 606: L´Epistre d'Othea by Christine de Pisan
fol. 34v