The most apparent difficulty in learning 14th century Germany is, of course, the language.

I listed some relevant books in Are there any history books on the Late Middle Ages? and in Any medieval history books or documentary recomendations for a beginner?, in addition to AH's book list on medieval Europe, but not so many German books on later Middle Ages, especially on its society and culture, have been either written or translated in English. Wilson's book on HRE (though in formidable size) and some of Ozment's works would be the solid departure point to HRE in Later Middle Ages.

I can at least add following books to them, however:

• Bumke, Joachim. Courtly Culture: Literature and society in the High Middle Ages, trans. Thomas Dunlap. Berkeley, CA: U of California Pr., 1991.
• Ohler, Norbert. The Medieval Traveller, trans. Caroline Hillier. Woodbridge: Boydell, 1995, 2010 (rev. ed.)

Both are translation of the classic but good introductory books by German medievalists published in 1980s (though the former mainly covers only up to ca. 1300).

• Rubin, Miri. Cities of Strangers: Making Lives in Medieval Europe. Cambridge: Cambridge UP, 2020.

This new book provides us with some convenient details on medieval city life, though not primarily restricted to Germany.

I really hope that Hanseatic cities are out of your interest, since most of few up-to-date English books on the Hanseatic league are either or both of highly academic nature or/and very, very expensive, in contrast to German one. I personally cannot guarantee the quality of every text found in the following 'official' site as well as BBC's Hansa and English, but at least they give some historical outlines better than Wikipedia (, and the former has some book guide, unfortunately most of them are in German):

• https://www.hanse.org/en/hanse-historic/the-history-of-the-hanseatic-league/
• BBC's introduction on the Hanseatic League (for BBC4's program below): https://www.bbc.co.uk/news/extra/A2MFANtn3Z/hanseatic_league
• BBC4's 'Hansa Inheritance' (Radio Program available for free): https://www.bbc.co.uk/programmes/m0006l6d

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What I can list as recommendable documentaries below are unfortunately only in German. I hope they can at least show you some example of clothing and streets in 14th and 15th centuries' Germany (German subtitle for those who with hearing difficulty is available in some videos, and all linked to the official streaming site of the broadcasting).

• Karl IV. und der Schwarze Tod: Zeit der großen Pest ('Charles IV and the Black Death: Age of the Plague') (2010)
• Die Deutsche Hanse (1/2): Eine heimliche Supermacht ('The German Hansa (1/2): A secret superpower') (2010)
• Die Deutsche Hanse (2/2): Eine heimliche Supermacht. Die Deutsche Hanse am Wendepunkt ('The German Hansa (2/2): A secret superpower') (2011)
• Ein Tag im Mittelalter: Ein Tag im Leben des Wundarztes Jakob Althaus im Jahr 1454 ('A Day in the Middle Ages: From the life of Surgeon Jakob Althaus in 1454') (2016)

(Edited): corrects a miss-translation of the German title of the documentary.