What did a Roman wear?
Why, a toga, of course.
Roman toga (public domain image)
Wasn’t that a troublesome garment to walk around in?
Yes, you had to readjust it constantly. Walking and talking with gestures messed it up.
How big was it?
6 meters of fine wool cloth cut in a circle.
In a circle?
Yes; that was one of its distinguishing features. The Greek himation was rectangular and its folds hung squared off at the bottom. The Roman toga-folds hung in curves.
Was it hard to put on?
It was best to have help. Doing it by yourself without a mirror (and no one had big mirrors) gave pretty bad results.
If it was such a troublesome thing why did people wear it?
Tradition. It became the symbol of Romanness and all Rome’s fine virtues. Only Roman citizens were allowed to put it on. People got sentimental about it.
How long was the toga worn?
All thoughout the Republic and the Empire. Give it a good seven or eight hundred years.
(I’m afraid a Roman would sneer at this Hollywood actor-friendly version of a toga. Compare it with the toga on this Roman statue. Notice the fold hanging out above the belly, and the tail hanging below the ankles.)
Statue of the emperor Marcus Aurelius (AD 161-180) wearing the toga (public domani photo by Klaus-Dieter Keller)
So much wool cut in a circle—it must have been expensive. How could the common Romans afford one?
Do you know about patrons and clients? In those days everyone except the emperor served somebody. Everyone was somebody’s “client”. A client made common cause with his patron, voted for him when he ran for office, walked around with him when he needed to show his support, served him in any way he asked. In return, the patron protected his client and saw to it that he was provided for. Once a year he gave him presents. One of those was a new toga.
Was the toga ALL they wore? Did they put on anything under it?
During the Republic they wore only a loin-cloth—just a linen cloth with the corners tied, as you see on a lot of Crucifixion pictures of Christ. Later they wore a long shirt—or two when it was cold. Augustus always felt chilly and Suetonius says he sometimes wore three and four of those linen shirts under his toga.
A man like Caesar was always conscious of how he looked and was forever watching his toga, making sure it hung properly and the folds were pretty. When the assassins began to stab him, his first thought was for his toga. He arranged it so that when he fell it would cover him decently. He had nothing on underneath but the loincloth.
How did they finally do away with the toga?
It wasn’t easy. Remember that, as it represented Romanness and Rome had great prestige, it looked very attractive to people. In a provincial town like Segóbriga in Spain, the natives must have looked with very wide eyes at the real Romans strutting proudly around in their togas. The statues of all the great figures of the past in the theater of Segóbriga (and everywhere) wore togas. It was the dress of heroes.
There was a ceremony when a youth first put on a man’s toga. In his home, in the presence of his relatives, he shed his boy’s toga with a purple band, the toga praetexta, and solemnly donned the pure-white toga virilis.
Toga praetexta (public domain image)
Not only the living relatives looked on. The ceremony took place in the atrium with the masks and busts of his famous forefathers. Afterwards they all went to the Forum where he inscribed his name on the list of Roman citizens and walked over to the Temple of Juventus and made an offering to thank the deity for safeguarding him until manhood.
But in time, yes, people wanted to get rid of it. Several emperors had to issue edicts ordering citizens to wear it every time they went outdoors. To go to the Colosseum, for instance. Privately, even the rich began to cheat a little and pull off their togas whenever they could. They felt comfortable only in a tunic.
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Great Names in History 
Was Suetonius his contemporary? Actually it kinda goes with his character: he had to make his exit on his own terms. Unbelievable.
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No, Erika, Suetonius was born more than a hundred years after Caesar was assassinated. His book is odd. With Livy and Tacitus you see a clear line. They were glorifying Rome. And Plutarch is a moralist. But Suetonius throws into his biographies the good and the bad without a comment. He even shuffles them together on the same page. Of Caesar he tells the most ugly gossip, which would make you conclude the guy was a monster. But then again he seems to make him into a hero and speak of him with admiration. Very modern, you might conclude–neutrality. Yes, but still you wonder where he stands and which of his anecdotes he doesn’t believe. If Caesar was as bad as you see him on the first pages, he was too disgusting to admire.
The toga looks very pretty, but very impractical. I’m surprised it lasted so long. Are you serious about Caesar? Did someon write about that? How can someone possibly control their dying moments??
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Erika: “Then, realizing that they were attacking him dagger in hand from all sides, he covered his head with his toga, while with his left hand he dropped the folds over the lower part of his legs so as to fall with more decency, with his body covered all the way to his feet.” Suetonius, Lives of the Twelve Caesars, Chapter LXXXII.