Rolo, for the most part, fails at "fashion". His default choices for clothing are usually either his school uniform or something with plenty of pockets for his guns, knives, and such. However, living with Lelouch and his brother's fabulous sense of fashion, Rolo's picked up a few things. Most of it, though, makes him look kinda young. Or something. But for the benefit of the people that interact with Rolo and for my own benefit, I'm posting a few of the kinds of outfits Rolo tends to wear.
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ref 3I tried to stay with Rolo's usual, canon-influenced clothing (even if some of them seem rather ridic, but hey) and where his canon clothing wouldn't fit for in game stuff, I went with fanart that seemed the most appropriate or fit with his clothing theme.
Most of Rolo's clothing is pretty high quality stuff. A good portion of it came from the previous Rolo and had been left with Jeremiah and Euphemia. Some was made by the previous Lelouch as well. Otherwise, Rolo shops at some of the nicer places in the market due to his adapted tastes (that he learned from Lelouch).