Gloves appear in two sets of contexts before the 16th century: in ecclesiastical and royal/ceremonial contexts, and in scenes of outdoor labor and falconry. It is only in the very end of the 15th century, and later, that they are worn as a fashionable accessory.

I've attempted to divide up the gloves by type. For additional information on the history of gloves and their manufacture, see these links.

• A rabbit-hunter wearing mittens in the January fresco at Castello Buonconsiglio, c. 1405-1410
• A leather glove, 15th century, found in London; additional views 1, 2, 3, 4, 5, and 6; also Two leather mittens (both for the left hand) were found in a chest on the Mary Rose (1545); a line drawing of one of them can be found on page 14 of the 2005 Annual Report of the Mary Rose Museum
• An infant's knit mitten, 16th century
• The Åsle mitten, c. 1510-1640
• A falconry party in the July section of the Augsburger Monatsbilder (1520s)
• Embroidered mittens, c. 1600 (V&A 1507&A-1882)
• Elizabethan gauntlet mittens, c. 1600
• Portrait of Henry Cary, 1st Viscount Falkland by Marcus Gheeraerts the Younger, 1603 (also here); it's more like a mitten-backing for a pair of fancy gloves.

• A field worker, a harvester, two shepherds (fol. 87v), men plowing a field (fol. 170), and a seed-sower (fol. 170v), in the Luttrell Psalter (British Library MS Add. 42130), c. 1325-1335
• Cain ploughs a field (fol. 6) and shepherds seeing the star (fol. 13) in The Holkham Bible (British Library MS Add. 47680), c. 1327-1335
• Ploughing scene, the Macclesfield Psalter (Fitzwilliam 1-2005, fol. 77r), c. 1330
• The Offering of the Heart, c. 1410
• August in the Les Tres Riches Heures du Duc de Berry, 1412-1416
• Shepherds in The Nativity by Robert Campin, 1425
• Annunciation to the Shepherds, book of hours (Bibl. Sainte-Genevive, MS 1277, fol. 053), c. 1433-1465
• Detail from The miracles of St. Leonard from the church of St. Leonhard bei Tamsweg in Salzburg, c. 1452-1461
• Detail from The Crucifixion from the altarpiece at St. Florian in Austria, c. 1475-1500
• Presentation scene, Chroniques de France et d'Angleterre (British Library Royal 14 D. V, fol. 8), late 15th century
• January in the Grimani Breviary, c. 1490-1510
• St Cecilia and her Fiancé by Cornelis Engebrechtsz, 1518-1520
• Portrait of Robert Cheseman by Hans Holbein the Younger, 1533

• Gloves said to be those of St. Hadelin, 11th-13th century
• Gloves of Roger II, c. 1105
• Effigy of Henry II, c. 1189
• Gloves of Emperor Frederick II (also here, c. 1198
• Effigy of Richard I, c. 1199
• The Three Kings before Herod, The Murthly Hours (NLS 21000, fol. 12r), 1280s
• Glove-plaques from the tomb of Jean de Chanlay, Bishop of Le Mans, 1291
• Silk liturgical glove, first quarter of the 14th century
• Bishop Wykeham's Glove, c. 1386
• Romans and their pontiffs, Ab urbe condita (BNF Fr. 271, fol. 66v), end of the 14th century
• Assassination of Onias III, Bible historiale (BNF Fr. 3, fol. 251v), beginning of the 15th century
Thane rysez the riche kynge ... His gloues gayliche gilte and grauen by e hemmys, With graynes of rubyes.

From Morte Arthure, c. 1440

• Coronation of Leo VIII, De casibus (BNF Fr. 234, fol. 183), third quarter of the 15th century
• Allegory: The cardinal virtues, The Book of the Treasure (BNF Fr. 191, fol. 119), second half of the 15th century
• Speculum Historiale, 1463: Heretics and ecclesiastics (BNF Fr. 50, fol. 2), Miracle of Our Lady: the fat abbess (BNF Fr. 50, fol. 246), the martyrdom of St. Savinian (BNF Fr. 50, fol. 324v), St. Taurin in front of the idol (BNF Fr. 50, fol. 364v), the martyrdom of St. Pothin (BNF Fr. 50, fol. 387), St. Firmin I preaches (BNF Fr. 51, fol. 69), St. Maximinus of Trier and St. Athanasius (BNF Fr. 51, fol. 132), the dream of St. Gregory of Nazianze (BNF Fr. 51, fol. 164), the miracle of St. Martin (BNF Fr. 51, fol. 297), and the translation of St. Martin (BNF Fr. 51, fol. 393v)
• Presentation scene, The City of God (BNF Fr. 18, fol. A), c. 1469-1473
• Roboam is dubbed by the emperor, The Knight Cifar (BNF Esp. 36, fol. 165v), fourth quarter of the 15th century
• The coronation of St. Julian, The Golden Legend (BNF 244, fol. 66v), c. 1480-1490
• Gloves from the tomb of Bishop Nicolaus Shiner, 1510
• Pope Sixtus IV and St. Ambroise and St. Augustine in The Triptych of the Immaculate Conception by Jean Bellegambe, 1526
• Knit silk gloves, possibly belonging to Archbishop William Warham

• The Manesse Codex (UBH Cod. Pal. germ. 848), 1300-1330: König Konrad der Junge (fol. 7r), Herr Wernher von Teufen (fol. 69r), Herr Ulrich von Gutenburg (fol. 73r), Herr Leuthold von Seven (fol. 164r), Herr Konrad von Altstetten (fol. 249v), and Kunz von Rosenheim (fol. 394r)
• St. Martin is Knighted (see detail) by Simone Martini, 1312-1317
• Solomon teaches, Bible historiale (BNF Fr. 8, fol. 249v), c. 1320-1330
• A falconer in the the Luttrell Psalter (British Library MS Add. 42130, fol. 159), c. 1325-1335
• A lady luring a falcon, the Taymouth Hours (British Library, Yates Thompson 13, fol. 74), c. 1325-1335
• Gauls and the Roman envoys, Ancient history until Caesar (BNF Fr. 251, fol. 247v), second quarter of the 14th century
• Ptolemy with a falcon, Der Naturen Bloeme (KB KA 16, fol. 85v), c. 1350
• The Marriage, 1350s
• Ivory mirror-back: A falconry party, 1350-1375
• A man with a falcon, from a minnekästchen, c. 1350-1400
• From the works of Guillaume de Machaut (BNF Fr. 1584), c. 1372-1377: Machaut and his alerion, Dit de l'alérion (fol. 96v); Machaut and the lover's servant, Fontaine amoureuse (fol. 161v); The allegory of the harp, Dit de la harpe (fol. 175v)
This hand borwen ofte to trewaunde with these gentel folk. In here grete haukinge glooves thei kunne putte it and hide it.

From The Pilgrimage of the Life of Man, c. 1450

• Hunting quail, Tacuinum Sanitatis (BNF Nouvelle acquisition latine 1673, fol. 72v), c. 1390-1400
• The book of Modus and Ratio (BNF Fr. 1297, fols. 54, 56, 58, 60, and 71v), first quarter of the 15th century
• Ptolemy with a falcon in Jacob van Maerlant's Der Naturen Bloeme (KB 76 E 4, fol. 47r), 1450-1500
• Homage of Roboam to the emperor, The Knight Cifar (BNF Esp. 36, fol. 164v), fourth quarter of the 15th century
• Hawking glove of Henry VIII

• The Maciejowski Bible, c. 1250: The elders meet Samuel, Saul gives Michal to David, David is applauded in Judah, Abner leaves, promising to build support in Israel, Joab slays Abner, Boaz encounters Ruth, David and Bathsheba get married, Absalom leaves David to plot a conspiracy
• Ahasuerus and his court, Bible Historiale (BNF Fr. 160, fol. 211), first quarter of the 14th century
• Allegory of Carnality, The Romance of Fauvel (BNF Fr. 146, fol. 12), 1320
• A seed-sower in the the Luttrell Psalter, c. 1320-1340
• St. Leonard in front of Clovis I, The Lives of the Saints (BNF Fr. 185, fol. 126), second quarter of the 14th century
• Bible historiale (BNF Fr. 162), third quarter of the 14th century: Moses comes down from Sinai (fol. 65), Moses receives the Law (fol. 91v), Moses and the Hebrews (fol. 112v), Hosea writing (fol. 123v), and St. Paul preaches (fol. 225)
• Leather glove, 15th century
• Guillaume de Digulleville and Idleness, The pilgrimage of human life (BNF Fr. 376, fol. 43), second quarter of the 15th century
• Negotiations in front of Marchot, Tristan de Léonois (BNF Fr. 112(3), fol. 66), c. 1470
• Gloves which belonged to Henry VI
• Portrait of Galeazzo Maria Sforza, Duke of Milan by Piero del Pollaiuolo, 1471
• Self-portrait at 26 by Albrecht Dürer, 1498
• Mary of Burgundy by Bernhard Strigel, c. 1500-1510
• Gloves reputed to have belonged to Henry VIII
• The lute-player (St. Mary Magdalene?), first half of the 16th century
• Gloves given by Henry VIII to Sir Anthony Denny
• Portrait of a lady by Paolo Cavazzola, c. 1515
• Portrait of Count Sciarra Martinengo Cesaresco by Moretto da Brescia, 1516-1518
• Portrait of a man by Moretto da Brescia, c. 1520
• Portrait of a young man by Jan Mostaert, c. 1520
• Portrait of a young lady by Bartolomeo Veneto, 1520-1530
• Balsam harvest, The Book of Simple Medicines (BNF Fr. 12322, fol. 187v), c. 1520-1530
• Portrait of a man with gloves by Titian, 1523-1524 (also here)
• Flight to Egypt in the Book of Hours of Françoise Brinnon (MMW 10 F 33, fol. 60r), 1524
• Portrait of Franois I, King of France by Jean Clouet, 1525-1530
• Portrait of Anton Fugger by Hans Maler
• Portrait of a man by Moretto da Brescia, 1526
• Portrait of a lady in a green dress by Bartolomeo Veneto, 1530
• Portrait of Lucrezia Sommaria (see detail) by Ridolfo Ghirlandaio, 1530-1532
• Portrait of a Roman courtesan by Parmigianino, 1530-1535
• Fol. 7v in the Hennessy Book of Hours, c. 1530-1540
• Portrait of a member of the Wedigh family by Hans Holbein the Younger, 1532
• Portrait of Charles V by Christoph Amberger, c. 1532
• Portrait of a member of the Wedigh family by Hans Holbein the Younger, 1533
• Portrait of a lady by Bernardo Licinio, 1533
• Portrait of Jean de Dinteville and Georges de Selve (The Ambassadors) by Hans Holbein the Younger, 1533
• Portrait of Charles de Solier, Lord of Morette by Hans Holbein the Younger, 1534-1535
• Portrait of Christina of Denmark, Duchess of Milan (see detail by Hans Holbein the Younger, 1538
• Portrait of a young woman and her little boy (see detail) by Agnolo Bronzino, 1540
• Portrait of a man holding gloves and a letter by Hans Holbein the Younger, c. 1540
• Portrait of De Vos van Steenwijk by Hans Holbein the Younger, 1541
• Portrait of an unknown young man at his desk by Hans Holbein the Younger, 1541
• Portrait of John Chambers by Hans Holbein the Younger, 1543
• Portrait of a gentleman with gloves by Lorenzo Lotto, c. 1543
• Portrait of Barbara Kressin attributed to Lambert Sustris, 1544
• Portrait of a Florentine noblewoman, 1540's
• Portrait of a woman holding gloves, c. 1540-1560
• Portrait of Barbara Kresslin, 1544
• White gloves attributed to the reign of Elizabeth I
By the Lady Mary Gray, 2 peir of swete gloves, with fower dosen buttons of golde, in every one a sede perle.
By the Lady Mary Sydney, one peir of perfumed gloves, with twenty-four small buttons of golde, in every of them a small diamond.
By Lichefelde, two peir of gloves perfumed.

From the New Year's Gifts to Queen Elizabeth, 1577-8

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By the Lady Waulsingham, 4 paire of gloves set with buttons of golde.
By Mr. William Russell, a paire of gloves, garnished with gold and sede perle.

From the New Year's Gifts to Queen Elizabeth, 1578-9

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By the Lady Walsingham ... a peire of perfumed gloves, the coaffe ymbrodered with seed pearle, and lyned with carnation velvett.
By Mr. Doctor Lopus, a peire of perfumed gloves.

From the New Year's Gifts to Queen Elizabeth, 1588-9

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By Mr. Josephe Lupo, one paire of pfumed gloves.
By Mr. Thomas Lupo, Josephe his sonne, one paire of pfumed gloves.
By Mr. William Warren, one paire of perfumed gloves.
By Mr. Peeter Guye, one paire of pfumed gloves.
By Mr. Jerolimo Bassano, one paire of perfumed gloves.
By Mr. Anthune Bassano, one paire of pfumed gloves.
By Mr. Edwarde Bassano, One paire of pfumed gloves.
By Mr. Andrewe Bassano, one paire of pfumed gloves.
By Mr. Cæsar Gallyardo, one paire of pfumed gloves.
By Mr. Trochins, one paire of perfumed gloves.
By Mr. Innocent Comye, one paire of perfumed gloves.
By Mr. Richard Graves, one paire of perfumed gloves.
By Mr. Walter Pearce, one pair of pfumed gloves.
By Mr. Robert Hales, one paire of pfumed gloves.
By Mr. Thomas Lupo, Peter Lupo his sonne, one paire of pfumed gloves.

From the New Year's Gifts to Queen Elizabeth, 1599-1600

• Gloves presented to Elizabeth I
• An Elizabethan glove
• Portrait of Mary Tudor by Anthonis Mor van Dashorst, 1554
• Lord Darnley's cuff, c. 1555
• Portrait of Mary Nevill, Lady Dacre, and her son Gregory Fienes, 10th Baron Dacre by Hans Eworth, 1559
• Glove of Mary Queen of Scots, 1560
• Portrait of an unknown lady, c. 1560
• Portrait of a gentleman, c. 1560
• Portrait of Alexander Farnese, c. 1560
• Portrait of Elizabeth I, c. 1560-1565
• Portrait of Charles IX, King of France from the workshop of Franois Clouet, 1561
• Portrait of Elizabeth Roydon, Lady Golding by Hans Eworth, 1563
• Portrait of Sir Thomas Howard, 4th Duke of Norfolk by Hans Eworth, 1563
• Shakespeare's gloves
• Portrait of Elizabeth Cornwallis, Lady Kytson by George Gower, 1573
• Woodcut of Queen Elizabeth from the Booke of Faulconcrie by G. Tuberville, 1575
• Portrait of Antonius Anselmus, his wife and their children by Marten de Vos, 1577
• Nobilis Neapolitana in Jost Amman's Trachtenbuch von Nurnberg, 1577
• Portrait of a man by Adriaan Key, c. 1580
• Portrait of Queen Elizabeth: The Welbeck or Wanstead Portrait by Marcus Gheeraerts the Elder, c. 1585
• Portrait of Elizabeth I, c. 1585-1588
• Pair of gloves, 1590-1610 (V&A T.145&A-1931)
• Portrait of Sir Francis Drake by Marcus Gheeraerts the Younger, 1591
• Portrait of George Clifford, Earl of Cumberland by Nicholas Hilliard, c. 1590; notice the Queen's glove in his hat
• Gloves in the Album Amicorum of a German Soldier, 1595: Cortegiana Romana, Governator di Roma, Castelan di Roma, Another lady, Another lady, Vedoua Senese, Duchessa di Venetia, Another lady, and Another lady
• Portrait of an unknown lady attributed to William Segar, c. 1595
• Miniature portrait of Sir Henry Percy, 9th Earl of Northumberland by Nicholas Hilliard, c. 1595
• A glove from Venice, c. 1600
• Portrait of Henry Wriothesley, 3rd Earl of Southampton by John de Critz, 1603
• Portrait of an unknown lady, c. 1603
• A pair of lady's knit gloves, first half of the 17th century
• Wedding gloves with symbols of love and marriage, c. 1622
• Pair of man's gauntlets, England, c. 1625-1650