Yes or no, depending on the version of Win Outlook you're using. Yes, and it depends on your first answer. I'm also assuming you're not using Mac Outlook 2004.
Outlook for Mac can only import
Unicode-based .pst files (Outlook for Windows) 2003 and later versions.
ANSI-formatted .pst files, were the standard personal folder format for saving data in Outlook for Windows in versions 97-2002 can't be imported into Outlook for Mac. I still have friends on Office 2000 or using Outlook 2002 (yikes!).
Regarding your data layout, keep in mind that you'll be left with a local data account - which is what you may be seeking anyway. I use Outlook 2013 and Outlook 2014 (Mac, just moved from 2011) - I prefer the Mac platform, and moved around 15 large PST files to a Mac-based server with Outlook 2011 running - the import of each PST file took a while, but the conversion was flawless. Keep in mind that the newer Mac versions of Outlook keep their messages "separate" in that they're not in one "lumped" file like a PST file, and your Mac will slow down for a while while Spotlight is searching through and indexing those new files.
I recently imported a PST (using Outlook 2011) with thousands of ZIP, CAD, PDF, and Office files - everything worked perfectly. My only issue was having to run out to buy a bottle of booze so that I could verify that all of the files were in fact properly imported. They were.
I have found that Outlook 2014 is faster than 2011 at importing, but the end results were the same. Make sure you get your edition of Mac Outlook updated before you begin the import - at least v.14.3.9 or newer as there were some pretty significant backend changes made in Outlook with that update.