Please be aware that some of the articles about trans and gender diverse people can be hurtful in their phrasings and tone. If you are triggered by something you read, please reach out for support to someone you can trust or to one of the organisations listed at the bottom of every page.
Discovering people wearing clothing not usually associated with their assigned gender at birth was treated variously through the newspapers at the time, from curiosity, disgust or amusement to admiration.
This great paragraph about the fact that women have been 'masquerading' as men for all of history (what it calls 'women masquerading as men', refers to various configurations of presentation / identity that go contrary to the societal norm of masculine and feminine) comes from the Kyneton Observer from an article about J. Jorgensen:
"It is an historic fact that no less than four Peninsula " veterans," who drew pensions to the day of their death for service under Wellington in all the great battles of the Peninsula, turned out to be women. Women masquerading as men have, in fact, been discovered every walk of life, from soldiers and sailors downwards; and one curious chapter in French history records the case of a Chevalier Beaumont; who was despatched on a special mission to Russia, and whose sex was vehemently (and on good grounds) suspected. The cases of women, indeed, who have chosen to renounce their sex and play the part of men would make a long and very interesting chapter of literature."
https://trove.nla.gov.au/newspaper/article/240876414
And one of the earliest recorded accounts of trans and gender-diverse people comes from Philo of Alexandria and Marcus Manilius in the 1 century CE, who wrote descriptions of transgender people during the early Roman Empire. Philo stated: "Expending every possible care on their outward adornment, they are not ashamed even to employ every device to change artificially their nature as men into women". He also attested that some members of this group, to that end, had their penises removed.
https://en.wikipedia.org/wiki/Timeline_of_LGBTQ_history
Occasionally, in the articles we've found, it describes people doing their own gender affirming care, such as someone assigned female at birth shaving their upper lip daily to result in a moustache, or another person assigned female at birth binding their chest to make it appear flat. You can find these mentions under the Gender Affirming Care tag.
You can find the articles broken into 'in masculine attire' and 'in feminine attire' just underneath this, or you can scroll further down the page to see the entire Trans and Gender Diverse collection.
Image: George M. Gould and Walter L. Pyle, Public domain, via Wikimedia Commons, https://upload.wikimedia.org/wikipedia/commons/7/76/Gould_Pyle_83.jpg