Pirate: During his imperial days, where he's more often than not paired with England.
Shotacon: He was shown to have creepy fantasies about the Italy brothers when they were barely teens. A deleted strip almost takes this too far, when Italy was a toddler.
Surprise Santa Encounter: Double Subverted. Belgium and Romano knew Netherlands was setting up a meeting with Santa... The surprise was when he brought a spaced-out Spain over his shoulder while dressed as reindeer. They were horrified, but at least no money was spent!
Team Mom: At start, being equal partners with Austria (or property?), and raising the boyish S. Italy.
Toros y Flamenco: Quite averted: he has only appeared in a matador costume in one official art, not in the strips, and doesn't seem to be a Latin Lover. The fanartists, on the other hand...
Word of God also says that he was two-faced like Russia and either very severe or cruel to his colonies that are not South Italy. To be fair, those notes are very old and were taken off Hidekaz's proper site, so we don't know how true they are right now. Volume Five profile does mention that he has a "mysterious aura of light and darkness," which might be a reference to the White Legend and Black Legend respectively.
This was mostly Played for Laughs with in the 2011 Fool's Bath. He gives a rather crazy look when France was about to spill who the true culprit of the event was, then he switched to his happy face and claimed that the letters he sent were meant to be a group hang out and not meant to be threatening.
Italy: Hey Germany! My older brother Romano is here, isn't he so cool?
Germany: Er, ya it's nice to meet you.
Italy: See I'm the Northern half, and Romano's the southern half! We were occupied separately, so my brother has been with Spain longer than he has with me! Come on Romano, say hello!
Romano: (to Germany) Munch on a bullet, potato freak.
The Dub Version has some interesting alterations note (Italy): Hey Germany, check it cool! This is my big brother Romano. Isn't he shizzy? **(Germany): I am Germany. A pleasure. **(Italy): I'm the north of the country, and he's the southern part. Since we've always been governed separately, he had to spend more time with our big brother Spain so he's become kind of a dick! Right? Now say "Hi" to my friend! **(Romano): (to Germany) Suck my balls, you damn potato eater! **(Germany): Uh!?
Dismotivation: From the Vol. 5 profile: "He does have the will to work, he just doesn't feel like it for now!"
Does Not Like Men: Rare male example. He's kind and flirtatious to women, but strict and asocial to men.
Sir Swears-a-Lot: Ties with England as the most foul-mouthed character in the entire series.
Spell My Name with an S: A bit lighter compared to the other characters, but some fans tend to use "Rovino," an actual Italian name meaning something along the lines of 'collapse,' instead of "Lovino," which isn't actually a given name (but a surname) but was just copied en masse due to L/R confusion.
Tsundere: South Italy is a fierce mix of all Type A varieties, partly out of insecurity that Spain only wants him for his inheritance and partly that his lack of domestic/artistic talents makes him inferior to his little brother. And yep, Romano's Tsundere side is specially strong when around Spain.
The Mafia: Seen once as thugs. Informs his outlook. It makes a lot of difference to the page quote which Italy you mean.
The Unfavorite: To some degree, especially during his "childhood" days when Spain was more fixated on North Italy than him. He was seriously worried that he didn't have anything to offer, lacking his brother's domestic and artistic skills.
It is hinted that the reason he is so mean to Spain is that he has abandonment issues-and considering that Ancient Rome chose to leave with North Italy instead, that Spain tried to swap him for his little brother, and that he thinks Spain only wants him for his inheritance, no one here can really blame him.
Oh, and Spain passed up saving Romano that one time because he had to make 500 roses instead. To be fair, Spain's own economy was in no condition to save anyone, and he also felt really bad about it.
Joshikousei: Her everyday clothes seem rather reminiscent of this, including a long, double-breasted pink coat with a sailor-style collar (pictured above) and a short sleeved purple dress that looks even more so. Subverted in the case of a sketch of her Gakuen design, as she wears a more Western style uniform much like Seychelles'.
Like Brother and Sister: Notes say her and France's relationship comes off as this. Although France being France, he probably doesn't see it the same way as she does.
Sempai/Kohai: Implied to be the nature of their relationship, as Monaco refers to Seychelles with the suffix "-kun", something often used by seniors referring to their kohai. Fandom often portrays them in this sort of relationship, or Monaco as Seychelles' Cool Big Sis.
When She Smiles: She's usually drawn looking like The Stoic, but smiled constantly during the 2011 Bloodbath, looking absolutely adorable.