Seems like, while it rarely snows in Rome itself, that there is freezing rain in the winter, and in the mountains, and rough weather any time. Yet we always see Romans depicted dressed for sunny days.
Weren’t sandals a poor choice in cold rain and mostly unpaved streets? Something more along the lines of moccasins would be appropriate.
And coats against the wind, and longer, monk-like robes with hoods in the mountains in winter.
Were these men, such great solvers of mechanical and engineering problems so unattuned to clothing?
Or are the images we see all based on those put on pottery and mosaics, presumably the elite posed in their finest sunny day wear.
Roman men only wore togas on formal occasions (think business suits today). The richer a man was he more occasions he’d have to wear one. Women did not wear togas unless they were whores or convicted adultresses.
If walking any distance, as for example in the army, men would wear boots.
Togas were ‘special’, and indeed recognised as inconvenient; normally men would wear a tunic and women a stola (basically a dress).
What is true is that Romans never wore trousers, and thought they were weird.
This is correct if by ‘boots’ you mean ‘really super-sturdy sandals’. The roman soldier wore something like these.
The toga was never worn as the only article of clothing. Under would be atleast two tunics, one being an “undershirt”, the other being the actual “clothes”. Think of the toga as a fancy jacket.
The military boots are called Caligae, and were so distinctive as to mark any man who wore them as a soldier (which is why modern drawings or films sett in Rome showing everyone, including slaves, wearing something like them are so silly.)
In fact, “Your mother wears Caligae” was a roman insult. It implied that said mother was a soldier’s whore. (That’s an anecdote by the way, so don’t quote me on it. It’s fun to use, though.)
BTW, the silly things are damned uncomfortable until you develop calluses. wince
I read somewhere that Roman soldiers stationed in Germanic areas of Europe wore enclosed boots during the winter.
Some modern-day echoes there. “Your mother wears army boots” is still extant, and the army surplus boots I bought as a student were also dammned uncomfortable until my feet adjusted 
Thanks for pointing that out, slaphead. I was afraid people would think I was joking if I did it
Aww, now you’re going and ruining my fantasies…
Can I still wear nothing under my toga at the next toga party and pretend we didn’t have this conversation? Yes? OK, great!
Ah, but women can wear bikinis 
In Soviet Russia, his mother probably does wear army boots. And she’ll hurt you.
Since I don’t attend toga parties, you can even skip the toga.
In cold weather Roman soldiers wore socks .
Roman’s would wear a Tunic, not a Toga. I’d call a Toga= suit or even a Tux.
They’d wear a sheepskin as a cloak in bad weather.
I know from experience one can wear shorts, sandals and heavy high wool socks and be fine even in quite cold weather.
The Toga was made out of wool and was thought to be rather warm wear.
Didn’t Cato go around wearing a toga without a tunic underneath? Something about the “traditional” way of wearing it.
Also, Colleen McCullough did massive experimentation with togas and wrapping while writing her excellent Masters of Rome series and determined that a man could not wear a loincloth under a toga. Something about how the toga was wrapped around the body and supported by the left arm meant that a man could not keep the toga on AND fiddle with a loincloth if he needed to urinate, and it was unthinkable a slave would help him with such an intimate thing.
She did twelve years of research before setting pen to paper (or fingers to keyboard, as the case may be) so take it for what it’s worth.
It would be more fun in Latin. Unfortunately Babelfish doesn’t do Latin.
My god. That saying now actually makes sense. “Mom” wears army boots because she got them from a solider - the old fashioned way. Which makes it a lot rougher insult than it is understood today. I can’t wait to use it.
A matter which has caused much frustration for me. (Can’t find a good Latin translator.)
Romans also wore closed shoes and boots.