If you want to have all your Outlook contacts available in your Apple's Mail application on your Mac, you'll need to get them all into the Contacts app. This entails a two-phase process. In the case of your Outlook address book, you'll have to save your contacts to a comma-separated value (CSV) plain-text spreadsheet—a format that's readily understood across both apps. Then, the application, which Mail uses for contacts management, can import the file and organize its contents with nary a hiccup.
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To export all the data from an OLM file of Mac Outlook to Windows Outlook, you need to convert it into PST format. There is a manual solution which can help you import OLM files data into Windows Outlook.