Export contacts from Outlook or Outlook Express (or any other application) to csv format and then import to gmail. That should do it for most users.
If you have your contacts on an old GSM phone, you could export them on to the SIM card and then import them to your new phone.
While you are there, try the “find duplicates” functionality. You can also add contacts into groups. The groups show up on your phone too after the sync.
Now on your android phone, browse to Contacts>Settings>Display options>Select “Only contacts with phones”, and also Google>Select all groups.
If you want to pull social contacts too, install the Facebook and Twitter apps and select to import data from all contacts. You should then see pictures and other address data added to your contacts auto magically.