Following are depictions of medieval men and women on pilgrimage. Trends to note: colors (brown or black), cloaks, broad hats, satchels (or "wallets"), staffs, and badges (especially the scallop-shell of Santiago de Compostela). There are also several manuscripts of Le pèlerinage de la vie humaine, in which the hero is depicted as a literal pilgrim; a few image-collections from some of the manuscripts of this texts are linked below.

Some additional links on pilgrims & pilgrimages in the Middle Ages, and on pilgrim's badges.

I especially recommend the Centrum voor Kunsthistorische Documentatie's Kunera for finding pilgrimage badges; for more information about Kunera (and how to navigate it), see Kunera: A Dutch saint and a database of badges and ampullae.

• Pilgrims on the tympanum of the Cathedral of Saint-Lazare, by Gislebertus, c. 1120-1130
Apparailled as a paynym in pilgrymes wise.
He bar a burdoun ybounde with a brood liste
In a withwynde wise ywounden aboute.
A bolle and a bagge he bar by his syde.
An hundred of ampulles on his hat seten,
Signes of Synay and shelles of Galice,
And many a crouch on his cloke, and keyes of Rome,
And the vernicle bifore, for men sholde knowe
And se bi hise signes whom he sought hadde.
This folk frayned hym first fro whennes he come.
'Fram Synay,' he seide, 'and fram [the] Sepulcre.
In Bethlem and in Babiloyne, I have ben in bothe,
In Armonye, in Alisaundre, in manye othere places.
Ye may se by my signes that sitten on myn hatte
That I have walked ful wide in weet and in drye
And sought goode Seintes for my soule helthe.'

Piers Plowman, Passus 5, lines 517-531

• Fresco of pilgrims at the Church of the Madonna del Parto in Sutri
• Pilgrims at the Holy Sepulchre (and Jerusalem?), History of William of Tyre, (BNF Fr. 2628, fol. 1), end of the 13th century
• St. James depicted as a pilgrim, The Lives of the Saints (BNF Fr. 185, fol. 47), 14th century
• The miracles of St. James, The Lives of the Saints (BNF Fr. 183), first half of the 14th century; fols. 39, 40v, and 41v
• Guide-book to Palestine for pilgrims, c. 1350
• The sick, the leprous, and the lame praying at St. Hedwig's tomb; pilgrims at St. Hedwig's tomb from Vita beatae Hedwigis (Getty Ludwig XI 7, fol. 87v), 1353
• Pilgrims from a fresco at the cloister of the Premonstratensian Order in Leles, Slovakia, c. 1350-1400
• A traveller and the patron saints of travel in John of Berry's Petites Heures (BNF Latin 18014, fol. 181v), ca. 1372-1390; note the badges mounted on the outside of the scrip
• Illustrations from a manuscript of The pilgrimage of human life produced in northern France in the early 15th century
• A barefoot pilgrim wearing red clothes in a missal (Universitätsbibliothek Graz 716, fol. 6r), c. 1400-1450
• The Pilgrims in The Ellesmere Chaucer, c. 1410
• The Voyages of Jean de Mandeville and the Liber peregrinationis by Ricoldo de Montecroce (BNF Fr. 2810), c. 1410-1412
  Illustrations of pilgrims bathing in the Jordan (fol. 129v), traveling (fol. 142v), paying tribute to the Saracens (fol. 170), at Sardonay (fol. 171v), in Tartary (fol. 173), in the Valley of Hell (fol. 215), travelling (fol. 265), at Nazareth (fol. 270), at Mount Carmel (fol. 270v), at Bethlehem (fol. 272), at the Holy Sepulchre (fol. 274), and at the hills of Lebanon (fol. 274v).
• St. James wearing a pilgrim's hat with shell badge, and carrying a scrip and a walking staff, The Hours of William Porter (PML M.105, fol. 29r), c. 1420-1425
• John Poloner's description of the Holy Land, c. 1421
• The Holy Pilgrims on The Ghent Altarpiece by Jan van Eyck, 1425-29
• St. John the Baptist and St. Jodocus, c. 1425-1435
• Marginalia depicting pilgrims on the road (apparently to Santiago de Compostela) accompanied by St. James, in the Book of Hours of Marguerite d'Orléans (BNF Lat. 1156 B, fol. 25), c. 1430
• Jodocius of Brittany wearing a pilgrim's hat with three scallop-shells, a scrip, and a staff, a book of hours (PML M.19, fol. 165v), c. 1440
They sawe þe man ... haue a-bowte his necke a skrippe and a staf in his hande, as he hadde ben a pilgryme of Seynt Jame.

Speculum Sacerdotale,
British Library MS Add 36791

• Jerusalem, The History of William of Tyre (BNF Fr. 68, fol. 98), third quarter of the 15th century
• John Lydgate and the Canterbury pilgrims leaving Canterbury, The Siege of Thebes (British Library MS Royal 18 D. II, fol. 148), c. 1455-1462
• Works of mercy: accommodating the stranger from an altarpiece at Trier, c. 1460-1470
• The martyrdom of St. James (BNF Fr. 50, fol. 268), St. Mary Magdalene and pilgrims (BNF Fr. 50, fol. 342), a pilgrim meeting St. Peter (BNF Fr. 50, fol. 342v), St. Arnoul of Yvelines on pilgrimage (BNF Fr. 51, fol. 420v), and St. Laumer gives alms to pilgrims (BNF Fr. 51, fol. 437v), Speculum Historiale, 1463
• Meal of the Pilgrims by Friedrich Herlin, 1466
• St. James, a book of hours (PML M.196, fol. 103v), c. 1470
• Christ, dressed as a pilgrim, approaching two disciples, also dressed as pilgrims, a book of hours (PML M.1001, fol. 80r), c. 1475
• Detail: St. Roche's hat (with three badges) and cloak, an altarpiece with St. Sebastian, St. Roche, and St. Wolfgang from Bad Aussee, c. 1475-1485
• Legend of St. James the Greater: The arrival of the pilgrims at the lodging-house from a Hungarian altarpiece, c. 1475-1485
• Legend of St Lucy, 1480: at left, St. Lucy and her mother on pilgrimage at the grave of St Agatha, with other (more typically-attired) pilgrims in the background.
• The Book of the Wanderings of Felix Fabri (c. 1480-1483)
• The legend of St. James the Greater: the landlord (innkeeper?) sneaks a silver vessel into the pilgrim's son's bag, from the altarpiece at Linz, c. 1480-1490
• St. James (note the shells, walking-staffs, and pilgrims' scrips in the border), a book of hours (PML M.234, fol. 37v), 1480s
• The hospitality of St. Roche in the Legend of St. Roche by Stefan Koblinger (fol. 1r), 1482
• St. James with a pilgrim, a book of hours (PML M.231, fol. 198v), c. 1485-1490
• St. James the Great as a pilgrim in a book of hours, c. 1490-1492
• Works of mercy: accommodating the stranger from an altarpiece at Linz, c. 1490-1500
• Thomas, a seven-year-old blind boy, on pilgrimage to the tomb of St. Louis, Life and Miracles of Saint Louis (BNF Fr. 2829, fol. C), end of the 15th century
• Canon Pietro Casola's pilgrimage to Jerusalem, 1494
• St. Jodocus wears a shell from Santiago de Compostela on his hat in an altarpiece from Innsbruck, c. 1495-1505
• Santa Croce from an altarpiece for a Dominican cloister in Augsburg, by Hans Burgkmair the Elder; see details for a group of pilgrims, a pilgrim, some pilgrims offered hospitality, and a seated pilgrim wearing a hat with badges and a vernicle
• St. Roche from a predella at Obere Fellach, c. 1505-1510
• Escape of St. Cantius, St. Cantianus, and Cantianilla, c. 1505-1515; in this detail, one can see the crossed-key badges and vernicles on Cantius and Cantianus's hats, indicating that they were pilgrims in Rome
• St. Paul and St. James the Greater (detail of the scrip) from an altarpiece by Gordian Guckh, c. 1510-1520
• St. Coloman from an altarpiece at Neuburg Cloister, c. 1510-1520
• A stone relief of a pilgrim by Hans Lutz at a church in Bolzano, c. 1513-1514
• Detail from St. Laurentius with the treasure of the church in front of Valerian, altarpiece at Graz, c. 1515-1525
• St. John the Evangelist, St. James the Greater, and St. James the Lesser from an altarpiece at Neukirchen am Ostrong, c. 1515-1525
GIVE me my scallop-shell of quiet,
      My staff of faith to walk upon,
My scrip of joy, immortal diet,
      My bottle of salvation,
My gown of glory, hope's true gage;
And thus I'll take my pilgrimage.

from The Passionate Man's Pilgrimage
by Sir Walter Ralegh, written c. 1603

• Woodcut of a pilgrim attributed to Albrecht Dürer
• Pilgrim badges in the borders of a Nativity scene in a book of hours from the first quarter of the 16th century (The Hague, MMW, 10 E 3, fol. 90v)
• St. James the Great as a pilgrim in a prayerbook (The Hague, MMW, 10 E 4, fol. 90r) c. 1525
• Queen Isabella of Portugal on pilgrimage, Genealogia dos Reis de Portugal (British Library Add. 12531, no. 9b), 1530-1534
• The pilgrim-mantle of Jakob Trapp VII, 1559
• The Pilgrims, Das Ständebuch, 1568
• Pilgrimage-clothing of Stephan III (c. 1570): hat and cloak, staff, and bag. (More photos available via Bildindex; select Orte from the top menu, then scroll at left to N and then pick Nürnburg; then click Sammlungen; Germanisches Nationalmuseum; Kunstgewerbe; Tracht und Kleidung, inkl. Zubehör; and finally Männerkleidung.)
• St Roche among the Plague Victims and the Madonna in Glory by Jacopo Bassano, c. 1575; note St. Roche's hat (with a pilgrim-badge) and cloak
• A True and Strange discourse of the traveiles of two English pilgrimes: What admirable accidents befell them in their journey to Jerusalem, Gaza, Grand Cayro, Alexandria, and other places by Henry Timberlake and John Burrell, 1601