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!
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 (1400-1420) Slovakia
Virgin and child from Ďapalovce
Bratislava, Slovenská národná galéria
15th century (ca. 1470) Germany
Virgin and Child by Master of the Life of the Virgin
last quarter of the 14th or first third of the 15th century century Italy
Virgin and Child with St Nicholas, St Catherine of Siena and donor by Gentile da Fabriano (1370-1427)
Berlin, Gemäldegalerie
http://onokart.wordpress.com/2010/04/02/giovanni-del-biondo/
late 15th century (1492-1498) Netherlands
Madonna in a Landscape by an unknown artist, possibly the Master of the Madonna Grog or Aert van den Bossche, formerly attr. to Master of the Embroidered Foliage
Minneapolis Institute of Arts
http://www.artsconnected.org/resource/1100/virgin-and-child-in-a-landscape
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
15th century Italy
sketch of the Virgin with Child by Pisanello from Codex Vallardi - INV 2590r
Paris, Louvre
http://fr.wikipedia.org/wiki/Fichier:Pisanello_-_Codex_Vallardi_2590_b.jpg
15th century (ca. 1455-1460) Netherlands
Madonna and child by Dieric Bouts
New York, the Metropolitan Museum of Art
http://www.metmuseum.org/Collections/search-the-collections/110000195
14th century (1370s) Italy
Madonna and child by Paolo di Giovanni Fei
New York, the Metropolitan Museum of Art
http://www.metmuseum.org/Collections/search-the-collections/110001696
15th century (1475-1499) Netherlands (Haarlem)
Virgin and Child by workshop of Dieric Bouts
New York, The Metropolitan Museum of Art