Lipgloss&Cigs.
My job is actually to promote the west strip of Queen b/w Bathurst and Gladstone (Called West Queen West). Apart from the incredible independent boutiques, there are phenomenal cafes, antique shops, Galleries and interior designers who would blow your f'in mind.
You are right though, i think the majority of Torontonians go where they know - Queen W (E. of Spadina), Yorkville, Bloor, etc...
Who would ever think to go to Queen E? Gerrard India Bazaar? Bloor West Village? Uptown to Lawrence Village? Makes me glad I know the city so well - it means never looking like I only know Aritzia.
Little Italy does have some great boutiques, though there was one particular one I am thinkng of near the fish shoppe (closer to Isabella I think), and I don't remember seeing her shop there the last time I was on College. I think it was called Ramona or something like that...
Anyhow - if anyone ever wants to know what's going on along West Queen West, shoot me a PM and I can give you my contact info. We have some great things planned for the neighbourhood in the coming months.