I'm also encluding some examples of hoods being worn in the "chaperone" style, as they sometimes provide good construction-related details. Additional pictures can be found here as well.
The Maciejowski Bible, 13th century Ruth dines with Boaz: Several men wear hoods, pulled back, with center-seamed white linen coifs covering their heads.
Manoah in the Psalter of St. Louis (BNF Lat. 10525, fol. 55v), 13th century; button-front hood (but could it be a hooded courtepy?)
The illustrations of Der tugendhafte Schreiber and Der Kol von Nssen in the Manesse Codex, 1300-1330, show two different styles of wearing similar hoods; in the former, fur-lined hoods are worn as chaperons, with a decoration at center front of the roll, whereas the latter wears the hood more conventionally, over a coif.
The feast of Job in a Bible historiale (BNF Fr. 164, fol. 150), 14th century; note what appears to be a single button under the chin, as well as a folded-back section at the top of the head
The Luttrell Psalter (British Library MS. ADD. 42130), c. 1325-1335
Working men in several illustrations seem to be wearing fairly simple hoods; the length of the tails and cowls varies quite a bit. (2, 4, 6, 7, 9, 10, 12, 15, 16 [note contrasting lining], 22, 23, fol. 80 [note boy carrying fruit in tippet], 30, 33, 34)
Fols. 4r, 25v, 40r, 44r, 52r, 56r, 59v, 109r, 113v, and 133v, Voeux du paon (Morgan Library G.24), c. 1350; notice contrasting lining in hoods, variety in dags, and unusual methods of wearing or draping the hood.
Le Roman de la rose, c. 1350 This illustration shows men wearing hoods with contrasting lining; one is worn with a brooch or ornament of some sort, another has an embroidered (?) pattern above a feathery dagged edge.
The Book of Modus and Ratio (BNF Richelieu MS Fr 12399), 1379: Men frequently depicted wearing hoods; the tails of some hoods are wrapped around the back of the head, or around the head; in some cases, there is a cap worn on top of the hood. A few examples of men wearing buttoned hoods.
Illustration from the Roman de la Rose, 1380 Narcissus is wearing a hood; about all that is visible of it is the extraordinarily long liripipe/tail at the back.
The Book of King Modus and Queen Ratio (BNF Fr 22545), end of the 14th century 72: Notice that the men's hoods match their tunics.
Laborer, Liber de Moribus hominum (BNF Fr. 1166, fol. 28v), end of the 14th century or beginning of the 15th century The face opening seems to be folded back, and there is a U-shaped dagging along the bottom edge.
De mulieribus claris (BNF Fr. 598) (BNF Fr. 598), beginning of the 15th century, shows several men in hoods, frequently with round dagging.
Several of the huntsmen in The Book of the Hunt (BNF Fr. 616), beginning of the 15th century, are wearing hoods, many of which have dagged edges.
Bible historiale by Guiard des Moulins, 15th century Several illustrations (available through Gallica or Mandragore) depict men wearing hoods in different manners.
April, Les Tres Riches Heures du Duc de Berry, 1412-1416
Border, The Hours of Margaret of Orleans (BNF Lat. 1156 B, fol. 135), c. 1426
Many of the 15th century workmen in the Mendel Hausbuch are wearing plain hoods.
The Nativity by Robert Campin, 1420-25 St. Joseph has pushed back his hood around his shoulders; the shepherds wear hoods too.
The Decameron (BNF Arsenal 5070), 1432 108v: The pious husband wears a blue hood. 215v: Men's hoods worn as chaperons/wrapped about the head. 223v: A baker wears his blue hood in the conventional manner, contrasting with the wealthier man wearing a chaperon. 304: A red hood worn under a fur hat, and a blue hood wrapped around like a chaperon. 347v: Two men wearing hoods, one of whom puts his on in the middle of the narrative. (The hood, I mean. The tail too, apparently.)
Suche a stinke in the chapell he hade, That dwelle ther he ne myghte. He stopput his nase with his hude; Nerre the chapell dur he yode, Anturs for to lere.
Seven Sacraments Altarpiece by Rogier van der Weyden, 1445-50 The chaperons and hoods in this detail of the left-side panel provide good details of various dagging styles
The Great Book of Hours of Anne of Brittany (BNF Lat. 9474), c. 1503-1508 January (fol. 4): a man wears a hood over a cloak but under a hat February (fol. 5): a subtle pattern (brocade?) on a hood worn with a hat
Women's Hoods
One thing I've noticed: I can find no examples in period illustrations of a woman wearing a dagged hood. Sure, I've seen them in dagged sleeves, and even in one example, a gown with a dagged bottom hemline ... but no dagged hoods.
I've found a few literary references, though. Margery Kempe, in a section of her writings posted as an inset further down on this page, describes herself ("this creature") as having been proud and vain, and wearing hoods with dagged tippets. (As discussed elsewhere on this site, it seems that "tippets" refer to the long tail of a hood, rather than sleeve-streamers.) There is also the green hood in a satirical mid-15th century poem, which is also described as "daggyd."
The Maciejowski Bible, 13th century Boaz encounters Ruth: Farmworker picking up grain (lower central part of illustration); notice white linen head-wrap worn under the hood.
The Luttrell Psalter (British Library MS. ADD. 42130), c. 1325-1335: Some of the women (like the milkmaid in fol. 163v) wear open hoods, sometimes over a veil (6)
Le Roman de la rose, c. 1350 This illustration shows women wearing hoods with contrasting linings; one of the women wears hers on the back of her head (see also the Romance of Alexander cited above).
Some of the women in Le Roman de la Rose (University of Chicago Library ), c. 1365, wear open hoods, some of which seem to have buttons; see fols. 80r, 81r, and 83r, for example.
Tacuinum Sanitatis, 15th century (BNF Nouvelle acquisition latine 1673), c. 1390-1400: Celery (fol. 28v); Hissop (fol. 29v); Marjoram (fol. 30)
Bible historiale by Guiard des Moulins, beginning of the 15th century The Judgment of Solomon (BNF Fr. 10, fol. 318): Two women wear open hoods. Birth of Israel (BNF Fr. 10, fol. 444): One woman's headdress looks like an open hood worn over a veil and wimple. Abraham travels: Sarah wears an open hood. The death of Job's children: The women wear open hoods; yellow (golden? brass?) buttons can be seen along the right edge of two of the hoods.
A shepherdess in the Rohan Hours (BNF Lat. 9471, fol. 85v); a bright red lining on the black hood
And, whan this creatur was thus gracyowsly comen ageyn to hir mende, sche thowt sche was bowndyn to God and that sche wold ben his servawnt. Nevyrthelesse, sche wold not leevyn hir pride ne hir pompows aray that sche had usyd befortym, neithyr for hyr husbond ne for noon other mannys cownsel. And yet sche wyst ful wel that men seyden hir ful mech velany, for sche weryd gold pypys on hir hevyd and hir hodys wyth the typettys were daggyd. Hir clokys also wer daggyd and leyd wyth dyvers colowrs betwen the daggys that it schuld be the mor staryng to mennys sygth and hirself the mor ben worshepd.
A woman wears an open hood with an almost exaggerated (wire-supported?) front in Terence's Comedies (BNF Arsenal 664, fol. 230v\, ca 1410
Les Tres Riches Heures du Duc de Berry, 1412-1416
Women in February, July, and September wear open hoods.
Border, The Hours of Margaret of Orleans (BNF Lat. 1156 B, fol. 135), c. 1426
The Decameron, 1432 Women wear open hoods in 108v, 215v (note buttons and seam), 304, 314, and
347v. Another 15th century illustrated Decameron (BNF Fr 239 has many more women in open hoods, some with buttons along one edge.
Lust, a book of hours (Morgan Library M.1001, fol. 98r), c. 1475
Livre d'heures de Charles d'Angouleme, late 15th century This illustration (also here) features a lady in a scarlet open hood with a long liripipe tucked into her belt.