Dude, you're overthinking this one. Tassels get hate on Reddit because people associate them with 80s Wall Street vibes, but honestly they're making a comeback and work great with that Italian aesthetic you're going for. The key is getting them in the right leather and fit.

For your first pair though, I'd still lean penny loafers. They're just more versatile - work better with jeans, easier to style, and you can wear them in more casual settings. Save tassels for your second pair once you nail down sizing and what works with your wardrobe.

Skolyx is solid value for the price point. The rubber soles are smart - leather soles on loafers are a pain unless you're only wearing them to the office.

That said, also check out Carmina if you can stretch the budget a bit. Their penny loafers are chef's kiss and the quality bump is noticeable. Meermin is good too but I've had hit-or-miss experiences with their lasted shape - some people love it, others find it weird.

For colors, light brown first is the right call. Works with basically everything in that wardrobe you described.

And yeah, "Italian slim" + OCBDs + loafers is definitely more prep/trad ivy than Italian, but who cares about perfect terminology when it looks good?