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.
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.'
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
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
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
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.
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.
The Pilgrims, Eygentliche Beschreibung aller Stände auf Erden, 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.)