The caligae are actually pretty comfortable, considering they are completely flat. They are made for right and left feet, unlike some ancient shoes. The caligae are actually boots, not sandles, and what sets them apart from Roman civilian footgear are the hobnails. During the Jewish war, the enemy could tell if it was Roman soldiers because of the sound of the hobnails. Those things grip the ground really well, but are deadly on hard surfaces, so you have to be careful walking on pavement, etc, or you go down hard when your feet slip.
Here are some shots from a march a few of us did last summer. You can see the Roman marching pack, which is more like a pole with the leather bag and other things lashed to it, and you carry it over your shoulder like a hobo pack. We did this along a rail trail in Northampton, got tons of weird looks (all reenactors are used to this, as are wooden bow archers, eh?), but some people who asked some good questions. The idea is to keep up a proper legionarie pace. No weapons, as we didnt want to hassle with getting permission this time, so we left our gladius and pugio in the cars. I am planning more extensive marches this year, something Legio III needs to do more of.
As for the calegia, I felt good after the march. Generally, you start to feel it after a full day of wearing the boots, but they work well and are pretty comfortable.
Dane
PS Notice the hat I am wearing, like Mike Houston's lol. There is pictorial evidence that Roman soldiers wore straw hats, odd as it may seem.
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