Never in shorts and never hatless.

I've read many memoirs in which captured soldiers express outrage at being deprived of their hats, and one instance in which a captured officer complained to one of the officers in charge of guarding him that he had been left hatless, whereby the prisoner was allowed, under guard, to search for another hat. So it was a big deal.

It appears that a white man in 1860 was expected to wear a hat when he was outdoors. And as far as I can tell, only barbarians and heathen savages willingly barred their knees in that era. Picture of POWs dressed in ragged pants that expose knees and legs describe them as "half naked."
 
I
Shorts were traditionally for children
I have a picture of my (very proud looking) granddad on the day he graduated to "long pants" instead of the the short pants and stockings little boys wore, so it seems reasonable that no self respecting man would want to wear anything but long pants if they were from that era.

And as I recall, the men would dunk their long shirts in water and put them on to stay cool when working outside on a hot day. The long sleeves also prevented sunburn back when there was no sunscreens. Per this article, sunscreens as we know them weren't invented until the 1930s and 40s.

 
I

I have a picture of my (very proud looking) granddad on the day he graduated to "long pants" instead of the the short pants and stockings little boys wore, so it seems reasonable that no self respecting man would want to wear anything but long pants if they were from that era.

And as I recall, the men would dunk their long shirts in water and put them on to stay cool when working outside on a hot day. The long sleeves also prevented sunburn back when there was no sunscreens. Per this article, sunscreens as we know them weren't invented until the 1930s and 40s.

Many westerns have yet to learn that, considering how many have shirtless scenes. Ew!
 
There was no historical interest or goal to develop a sun-burn, much less a sun tan. Men customarily wore hats... even when they had to weave them themselves from palmetto (which was evidently not uncommon). Wearing a dilapidated hat was evidently considered less odd than wearing no hat at all...

"The cracker is independent in his ideas of dress or costume. A felt hat of a nondescript color, but once probably white...completes the costume..." (Lippincott's Magazine, 1870).

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Most Southern country women didn't bother about hats, but wore "cracker bonnets" generally with "curtains."

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It was frequently observed among country southerners that their garments were constrained in length, rarely reaching their ankles... evidently a result of the width of their customary homespun goods. Both the men's trousers and women's "cracker gowns", making ankles frequently obvious...

Crackers near the Georgia-Florida borderlands... (1858):

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Evidently, even when wearing ankle length trousers, the crackers frequently rolled them up several inches...

The cracker is independent in his ideas of dress or costume. A felt hat of a nondescript color, but once probably white, a cotton shirt innocent of plaited bosom, starch or washing, and a pair of homespun or "hickory" trousers stuck into his boots, or, more generally, rolled up about half a foot above low-quartered brogans, and showing an expanse of dirty ankle, complete the attire of the man. The woman wears a homespun gown; I cannot positively aver that she does not wear anything else, but, to the best of my knowledge and belief, she does not. Children wear anything or—nothing." [Lippincott's Magazine, 1870, 465.]

1860s illustrations of contrabands etc. in the South occasionally show the trousers rolled up above the ankles...

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Common women's skirts were evidently often rather shorter than the fashion too... From about Vicksburg, from a Union soldier:

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Again from the Georgia piney woods...

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Syrgley's "Seventy Years in Dixie" (1891), based on his own recollections and the statements of T.W. Caskey, laments that the plain common dress of the mid-19th Century Southerners was so ill considered as to have been practically undocumented outside of the observations of swells, in favor of the portraiture of folks with money...

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