Crying seems to have been a very manly thing in the late 1700s, and even in the early 1800s. At the time, manliness had two components - the plain-speaking, patriotic, independent man, and the paternal, emotional family man, which were combined in the ideal. An example comes from the ballad 'The Sailor's Tear', from 1835:

He leap’d into the boat

As it lay upon the Strand;

But oh! his heart was far away,

With friends upon the land,

He thought of those he love’d the best,

A wife, and infant dear, —

And feeling fill’d the Sailor’s breast,

The Sailor’s eye, — a tear.

Of course, this is only true in the context of domesticity; men were expected to have strong feelings about their family, but were still expected to maintain the traditional masculine virtues of stoicism and courage. Even so, Royal Navy sailors wept at Nelson's death, and this was celebrated by society.

Source:

Weeping Sailors: British Manliness 1760-1860, Joanne Bailey, http://www.britishnavalhistory.com/weeping-sailors-british-manliness-1760-1860/

Shakespeare predates the times asked about in this question, but for what it's worth, in his plays (circa 1600), when men cry, it's generally labeled as effeminate.

From "As You Like It":

"ROSALIND [Disguised as a man.] Never talk to me; I will weep.

CELIA Do, I prithee; but yet have the grace to consider that tears do not become a man."

From "King Lear":

"I am ashamed That thou hast power to shake my manhood thus; That these hot tears, which break from me perforce, Should make thee worth them."

And leaping to the other end of time-period, to 1887, here's a quotation from Strindberg's play, "The Father." (Which alludes to "If you prick us, do we not bleed..." from Shakespeare's "Merchant of Venice.")

"LAURA. What! You are crying, man!

CAPTAIN. Yes, I am crying although I am a man. But has not a man eyes! Has not a man hands, limbs, senses, thoughts, passions? Is he not fed with the wine food, hurt by the same weapons, warmed and cooled by the same summer and winter as a woman? If you prick us do we not bleed? If you tickle us do we not laugh? And if you poison us, do we not die? Why shouldn't a man complain, a soldier weep? Because it is unmanly? Why is it unmanly?

LAURA. Weep then, my child, as if you were with your mother once more. Do you remember when I first came into your life, I was like a second mother? Your great strong body needed nerves; you were a giant child that had either come too early into the world, or perhaps was not wanted at all."

Perhaps "crying" is too broad a term. It runs the gamut from a tear squeezing out your eye under great emotional stress, to blubbering like a child. And a lot of stuff in between. There is also the issue of crying from what? Many strong emotions can provoke tears, and not all of them involve sadness or misery, which is what we usually associate with crying.

My impression from what I've read is that the answer to these questions would matter very much, in considering how people viewed it. There might be nothing shameful about shedding some tears of sorrow at the death of friends or family, but sobbing uncontrollably could be considered unmanly.

The Victorians, for example, were not unsentimental people. There are lots of examples in period literature of what we might today even call overblown emotions, extreme by modern standards, at least in anglophone countries. Melodramatic at times. They did not despise sorrow, or the response to it. On the contrary, the understood it well. Tears alone would not carry stigma.

What they considered unmanly was helplessness. "Being a man" didn't mean you never shed a tear. It meant you didn't sob like a child, you didn't whimper, wail, fall apart, lose control completely.

So I think we should consider these questions when quoting literature from this period. What exactly did the "crying" consist of, and what was the context.

I just recently finished Roger Crowley's "City of Fortune: How Venice Ruled the Sea". This isnt quite England but I do know Venice had the help of English soldiers in multiple battles. Throughout these battles, when something unexpectedly good happens, the doge and nobles break down and weep.

According to Lars Brownsworth's book on the Byzantines, the Western Crusaders from Lombardy, France, and England felt the Byzantines were effeminate, so they at least felt themselves to be quite masculine.

This may be a bit of a stretch, but I've recently been reading Lord of the Rings, and characters who are meant to appear strong and valiant shed tears. While fictitious, it does indicate that crying wasnt seen as unmanly in England around the time it was written (post-WW2 I believe).