Tailored Suits Florence/Milan

Your post is labeled "tailored suits" but you don't mention that in your post. I don't know anywhere in Europe where it is possible to have a suit tailored for anything under about $1,000, and many cost several times that amount. Considering the time that it would cost to have a suit tailored for you, complete with multiple fittings, I think you might be better looking at something off the rack.

I was considering hitting a tailor in Naples but my trip doesn't last long enough and the monetary investment exceeds my desires for a one off suit.

If by "tailored" you mean a good quality Italian suit, then you might try Santini at Via Luigi Alamanni 35r right across from the SMN train station. It's an outlet so it will be hit or miss as to whether you find a suit that fits your requirements (size, quality, color, cut), but the price will be good if you do. I've purchased several items of clothing there, and when I get around to buying a suit that's where I would start looking. Their hours are 9:30-7:30 Tuesday thru Saturday, with shorter hours on Mondays and closed most Sundays.

Surprisingly the big department stores sell mostly well-known suit brands that you can buy worldwide, so no point in shopping at them.

For Florence I second the suggestion of Santini, on Via Alamanni, basically across from the station on the Bar Deanna side (Florentine for west side of the station). Santini has the best prices in the city center and probably the only place downtown where you have a chance of finding a business suit for under 400€.

Tailored suits cost much more than that, sorry,

It depends on the material of the suit. In Milan, the cheapest tailored suit you can get starts around €500.

Thanks for the advice - I ended up buying a nice Cerruti suit in Milan for $350 with immediate free alterations