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!
second quarter of the 14th century (1340s) South East England - London?
British Library, Egerton 2781: the Neville of Hornby Hours
fol. 71r - Annunciation
ca. 1500, French - Tours
Bibliothèque de Genève
Comites Latentes 124: Book of Hours
fol. 108v - coronation of the Virgin
15th century (ca. 1475), Spanish
Barcelona, Museu Nacional d’Art de Catalunya
Birth of the Virgin by Workshop of Pedro García de Benabarre
first half of the 14th century (ca. 1300-1330), French - Champagne
Enthroned Virgin and Child
Met
http://metmuseum.org/Collections/search-the-collections/170007605
15th century (ca. 1490) Germany - Konstanz
Einsiedeln, Stiftsbibliothek
Codex 710(322): Writings by Heinrich Seuse
fol. 42r - Seuse kneeling before Mary and Jesus
beginning of the 16th century (ca. 1500) France - Rouen
University of Oxford, Bodleian Library
MS. Buchanan e. 3: Book of Hours
fol. 21r - Visitation (Mary and Elizabeth)
http://www.bodley.ox.ac.uk/dept/scwmss/wmss/medieval/mss/buchanan/e/003.b.htm
later 15th century (after 1471) Northern Netherlands - Enkhuisen?
University of Oxford, Bodleian Library
MS. Buchanan f. 1: Book of Hours
fol. 10v - detail of the Virgin from the Annunciation
Mary is inside, with her hair loose and only in her kirtle. Although images of this one figure can be hardly ever classified as accurate depictions of contemporary fashion (her hair is loose most of the time and the gowns she wear are really never in the-latest-trend style), this particular detail shows a lovely example of 15th century kirtle. It is laced in front, the neckline is a deep scoop and the bodice is tightly fitted (although the sleeves are not).
http://www.bodley.ox.ac.uk/dept/scwmss/wmss/medieval/mss/buchanan/f/001a.htm
beginning of the 16th century (ca. 1500) France - Rouen
University of Oxford, Bodleian Library
MS. Buchanan e. 3: Book of Hours
fol. 74r - Virgin and Child with what is probably a female owner of the book
The owner is depicting wearing the typical late 15th/early 16th century fashion. The black hood is a predecessor of later French hoods (A beautiful example of a something-in-between hood can be seen here. Basically, the wings of the hood (the rectangle of fabric framing the face) became the frontlet, acquiring the jewelled part called the billiment in the process. These type of hoods were around for a long time before, in many variations - buttoned in front with long hanging tip, with widened wings, combined with hennin etc. etc.)The neckline is deep and squared and edged - same as the cuffs of the long, broadening oversleeves - in what is probably white fur. There is a rosary hanging at the woman’s girdle and she seems to be wearing a necklace which creates a typical v above her bodice.
http://www.bodley.ox.ac.uk/dept/scwmss/wmss/medieval/mss/buchanan/e/003.b.htm
14th century (ca. 1330) France - Normandy
13th century (ca. 1220-1230) Italy (Tuscany - Prato)
sculpture of Virgin Mary, originally located in Prato Cathedral
Paris, Musée de Cluny
http://www.sculpturesmedievales-cluny.fr/notices/notice.php?id=728