How does a fresh graduate start his dress shoe arsenal?

[josepidal]

(Caveat: I live in Manila, near the equator in Southeast Asia. Our concept of formal wear here is limited to a suit, and the tuxedo is both nonexistent and impractical. One rung below that and what passes for office attire is a long-sleeved shirt and tie, possibly with khakis or chinos. Smart casual wear or some tropical-region version of business casual follows.)

I have been browsing the shoe threads in this forum and read Alan Flusser.

http://www.boo.com/flusser_book/doc/ch5.htm

I realize that my leather shoe collection might be deficient, and I might be working in a law firm soon. At the very least, I need things that go with a tie, without any jacket or blazer (see above caveat).

At present, I have only three shoes anywhere near business or formal shoes:

--pair of black brogue wingtips I got when I was 14, still good

--pair of brown Cole Haans I was told were dress shoes but are apparently very casual in North America and Europe

--pair of black plain-front, square toed black chelsea boots (they actually look good on me because they don't look metrosexual and I'm a short, young Asian... don't argue, I trust the opinion of females in every class in my grad school, plus their boyfriends who want to get a similar pair)

Nothing like the closetfuls of Edward Greens and Lobbs I keep seeing here, eh?

So the next time I go buy a dress shoe -- by Flusser definitions this time -- what is most practical for me to begin with?

I imagine I should get a close-laced, cap-tipped, no brogue black shoe. However, seeing I already have something in black, should I get something like that but in cordovan?

Also, is a monk strap equivalent of an open-laced shoe formal enough for a suit? Or is formal limited to lace-ups?

Also, how are Italian dress shoes for you guys? I notice no one mentions them, like Ferragamos. Do they only go with a certain Italian cut of trouser or suit?