What musicians wore, and which sorts of instruments might have been considered appropriate or typical for men or women of different social classes.

My rules for inclusion in this list:

1. The dress of the musicians must at least approximate contemporary dress to the period in which the painting was done;
2. The musicians must be human, and not angels, demons, gods, etc.;
3. The artwork must have been executed post-Antiquity but before 1600.

There are several pictures of trumpeters calling noblemen to their meals; see the page about feastgear for such illustrations, and the bannered trumpets too. There's also the Research Center for Music Iconography and Prof. Mary Rasmussen's Musical Iconography, as well as Bagpipes in Medieval Manuscripts (and other Bagpipe Iconography) and Historische Abbildungen (artwork with lutes, citterns, or guitars).

See A Guide to Medieval and Renaissance Instruments for more information about the different instruments discussed below. (Some of the instruments below may be mis-identified; please contact me if you've got a better idea of what we're looking at in these pictures.)

• A man plays a stringed instrument and dances, Silos Apocalypse (British Library MS Add. 11695, fol. 86), 1109
• Sacred and profane music (fol. 1r) and a musician playing the vielle with a dancing woman (fol. 182r), a psalter (St. John's College MS B 18), early 12th century
• King David with other musicians, a psalter (St. John's College MS K.30, fol. 86r), c. 1190-1200
• Illuminations from The Cantigas of Santa Maria, 13th century
• An Irish musician plays a harp, Topographia Hibernica (British Library MS Royal 13 B. VIII, fol. 26), c. 1220
• The Maciejowski Bible (PML 638), c. 1250
  The Israelites rejoice (fol. 9): A young woman plays a round frame drum (timbrel?) with two beaters.
  Joshua battles Amalek (fol. 9): Accompanying the men into battle are trumpet-players and drummers.
  Jephthah returns home (fol. 13): One of Jephthah's daughters plays a square hand drum (timbrel?).
  Men of the land of Benjamin take daughters of Shiloh as wives (fol. 17): Two musicians (at left); one plays the viol, the other plays pipe and tabor.
  The Ark Of The Covenant (fol. 20): Two men play trumpet.
  Samuel and Jesse (fol. 25): David plays pipe and bell; his harp rests against a tree.
  Saul is troubled, Jesse's offerings to Saul, and David plays his harp for Saul (fol. 26): David holds or plays a harp.
  The women of Israel greeting David after the death of Goliath (fol. 29r) (also here: A young man plays a viol/vielle; two young women play drums (timbrels?), one a round frame drum with two beaters, the other a square drum; another young woman plays bones.
  Saul envies David (fol. 29): Young David carries a harp.
  Saul attempts to slay David (fol. 30): David carries a harp under his arm.
  David brings the Ark to Obed-Edom (fol. 39): David plays a harp, as several young men play musical instruments: (from left to right) a set of bones in each hand; pipe and bell; two trumpets; viol/vielle.
• A musician plays pipe and tabor as a female acrobat dances, Cartulary of Battle Abbey (British Library MS Cotton Domitian A. II, fol. 8), 13th century
• The Manesse Codex, 1300-1330
  Several of the illustrations feature musicians playing various instruments.
• Procession from the Scenes from the Life of the Virgin, Cappella Scrovegni, Padua, by Giotto di Bondone, 1304-06
  The procession passes three men; one plays a vielle, another plays a transverse flute, and the other seems to be playing a rackett.
• A boy plays a rebec for the feast at the Wedding of Cana (fol. 168v), Dancing musicians playing mandora and rebec (fol. 174), women playing tamborines (fol. 182), and four men singing (fol. 196v), The Queen Mary Psalter (British Library MS Royal 2 B. VII), c. 1310-1320
• A drummer and trumpeter, a book of hours (British Library MS Stowe 17, fols. 95v-96), c. 1310-1320
• St. Martin is Knighted, fresco in the Cappella di San Martino, Lower Church, San Francesco, Assisi, by Simone Martini, 1312-17
  One man plays a pair of fipple flutes; another plays a lute. Behind them are a pair of singers. They are easier to see in this detail
• Musicians play tabor and bagpipe to accompany dancers, Roman de la Rose (British Library MS Royal 20 A. XVII, fol. 9), first half of the 14th century
• The Feast of Herod, from the Scenes from the Life of St John the Baptist, Peruzzi Chapel, Santa Croce, Florence, by Giotto di Bondone, 1320
  A man plays a rebec to one side of the feast-tables.
• Drummers and mummers at the wedding celebration for Fauvel, Romance of Fauvel (BNF Fr. 146, fol 36v), c. 1320
• The Luttrell Psalter (British Library MS. ADD. 42130), c. 1325-1335
  Illustrations of musicians (fol. 176), including men playing the portative organ, bagpipes, nakers, a hurdy gurdy, and a pipe & tabor.
• A man plays pipe & tabor while another balances on his head in Glossa ordinaria in Librum Sextum (St. John's College MS A.4[IV], fol. 60v), c. 1335-1350
• A boy plays vielle at Ataxerxes' banquet, Speculum Humanae Salvationis (ÖNB s.n. 2612, fol. 45r), c. 1330-1340
• Romance of Alexander (Bodley 264), c. 1338-44
  51v: Five young men play instruments on the roof of a castle -- two horns, a portative organ, a rebec, and a cittern.
  70r: A man plays the pipe and tabor for a busker in a deer costume.
  79v: A woman playing the vielle.
  117v: A man plays the pipe and tabor for a dancing bear.
• Musicians play pipes (one with tabor) to accompany a female acrobat balancing on swords (fol. 58) and a man plays pipe and tabor while a boy stands on his shoulders (fol. 94), Smithfield Decretals (British Library MS Royal 10 E. IV, fol. 58), c. 1340
• The Marriage by Nicolo da Bologna, 1350's
  Entertainers at the wedding include a woman singing while playing the vielle, two men playing the trumpet, and a man playing drums.
• Dance of Salome in John of Berry's Petites Heures (BNF Latin 18014, fol. 212v), ca. 1372-1390
  She seems to be singing and accompanying herself on a timbrel.
• Sleep (fol. 97), music (fol. 101v), and song & dance (fol. 102), Tacuinum Sanitatis (BNF Latin 9333), 15th century
• Music, Tacuinum Sanitatis (BNF Nouvelle acquisition latine 1673, fol. 86), 15th century
• The Garden of Eden, 1410
  St. Cecilia plays a psaltery.
• Virgil's Opera Omnia, ca. 1450-1475 (The Hague KB 76 E 21 I) features pictures of shepherd-flutists: Flute-playing contest between Menalcas and Dametas with Palemon as judge (fol. 20r); Mopsus and Menalcas about to play a song eulogizing Daphnis (fol. 25r); Flute-playing contest between Corydon and Thyrsis with Daphnis as judge (fol 30r)
• The sanguine temperament: A man plays a lute while a woman plays a harp, a calendar (British Library MS Add. 17987, fol. 86v), 1446
• Speculum Historiale (BNF Fr. 51), 1463: St. Cecily, Valerian and Tiburtius (fol. 8) with a trio of musicians; St. Paphnuce of Heraclea (fol. 158v) with a musician playing a hurdy-gurdy.
• A lutenist and harpist in the Garden of Love by Bartolomeo Baldini Baccio, 15th century
• Sol and His Children, the Wolfegg Housebook, 1475-1485
• A viellist and lutenist accompany an acrobat in the works of Heinrich von Veldeke (ÖNB 2861, fol. 95r), c. 1474-1574
• The Triumph of Venus, fresco in the Palazzo Schifanoia, Ferrara, by Fracesco del Cossa, 1476-84
  Young women (visible in this detail) hold lutes and recorders.
• Detail from a mural with dancers and the prince-electors at Zvikov, c. 1480-1500
• Concert by Lorenzo Costa, 1485-95
  A man plays a lute; he sings, accompanied by a man and woman behind him. There is also a rebec, resting on the table.
• The Marriage of Mary, fresco in the Cappella Tornabuoni, Santa Maria Novella, Florence, by Domenico Ghirlandaio, 1486-1490
  This detail gives a better view of two men playing pipe and tabor in the background.
• The Lute Player and the Harpist, Israel van Meckenem the Younger, 1490
  A lady plays the harp, while a man plays a lute. (The lute-case is visible next to the stool the man is sitting on.)
• Archery Festival, 1493
  Several men are either playing or carrying musical instruments. A dark-skinned man dressed in Italian (?) fashions plays a tabor. A jester carries a bagpipe tucked in his belt.
• Illustration from a book of hours, c. 1500-1525 (The Hague, MMW, 10 F 14, Fol. 9r)
  While riding a boat, a man plays a wind instrument, and a woman plays the lute.
• Two Musicians by Albrecht Dürer, 1504
  One man plays a wind instrument (possibly a shawm) and another accompanies him on a tabor.
• The Lute Player by Andrea Solari, 1510
• May from the Da Costa Hours (PML M.399, fol. 6v), c. 1515
  A spring afternoon on a rowboat. A young man plays a shawm; a girl plays a lute.
• A fife-player and a lute-player (in a collection of images relating to Landsknechte and Kampfrauen)
• The Minstrels’ Pillar in St. Mary’s Church, Beverly, c. 1520-1524
• A Concert, mid-1520s
• The Concert by Callisto Piazza, c. 1528-1530
• Fol. 5v in the Hennessy Book of Hours, c. 1530-1540
• Lady Playing a Lute by Bartolomeo Veneto, 1530
• Concert of Women by the Master of the Female Half-Length, 1530-40
  Three young ladies; one plays a lute, another plays a transverse flute, and the third seems to be singing along.
• Flute quartet and country concert in the frescos at the Castello del Buonconsiglio by il Romanino, c. 1531-1532
• The lute-player (St. Mary Magdalene?), first half of the 16th century
• Woodcut of a piper and lute-player by Edward Schoen, 1535
• Henry VIII's wind band in the gallery at Whitehall by Hans Holbein
• The Fountain of Youth by Lucas Cranach the Elder, 1546
  In this detail, musicians playing a flute and tabor drum are dressed all in white.
• A concert in a garden, second part of the 16th century
• Children's Games by Pieter Bruegel the Elder, 1559-60
  In this detail, a young girl plays the pipe and tabor.
• The Triumph of Death by Pieter Bruegel the Elder, 1562
  A lady sings, accompanied by a man playing a lute; they are easier to see in this detail.
• Pierre de Moucheron, Merchant of Middelburg and Antwerp, and his family, 1563
  A girl plays a keyboard-based instrument while the rest of the family dines (or at least poses around the table).
• The musicians in The Wedding at Cana by Paolo Veronese, 1563
• Detail of a young man playing the lute for a fresco of dancers at Villa Caldogno by Giovanni Antonio Fasolo, c. 1565
• Detail of a young woman playing the lute for the concert fresco at Villa Campiglia Negri de' Salvi by Giovanni Antonio Fasolo, c. 1565
• Peasant Wedding by Pieter Bruegel the Elder, 1568
  Two men play bagpipes to entertain the banqueters.
• The Peasant Dance by Pieter Bruegel the Elder, 1568
  A man sits and plays the bagpipe for the dancers.
• The Singer, The Organist, The Harpist and Lutenist, Three String-Players, Three Fifers, and The Drummer, Das Standebuch, 1568
• Fête at Bermondsey by Joris Hoefnagel, 1569
  Two fiddlers (lower right-hand corner) prepare to play for the festivities. They wear similar scarlet outfits.
• A concert, c. 1580
• A ball in Augsburg, c. 1590-1595 (musicians in the balcony playing wind instruments, and a musician playing vielle)
• Singers and musicians, Album of Hieremias Buroner (British Library MS Egerton 1554, fol. 2), c. 1592-1599
• Dancers and musicians, Album of Johannes Cellarius (British Library MS Add. 27579, fol. 149v), c. 1600-1606
• An open-air banquet, with musicians playing lute and viol, Album Amicorum of Moyses Walens (British Library MS Add. 18991, fol. 64), c. 1605-1615