Initially, I didnt like using gmail, but ever since I’ve started using Google Apps to manage my personal emails, I’ve fallen in love with the gmail interface, and wanted to move all my Outlook emails to gmail.
I tried using the GML software but it required the .NET framework, and often hung without uploading all the emails.
Here is a very easy way to upload your Outlook mails to Gmail, without the need of any software.
Step 1: Enable IMAP on your Gmail/Google Apps account. This step by step tutorial tells you how to enable IMAP.
Step 2: After you configure GMail on your Outlook (as part of the above step), you will see the IMAP folder (Gmail) and it will list out all the labels that you use as separate folders.
Step 3A: If you dont not wish to maintain a backup of the emails in Outlook, and just want them in your gmail inbox, drag the mails to your gmail Inbox (Under IMAP folder). If you drag them to your labels folder, they will automatically be labelled.
Step 3B: If you do wish to keep a copy of all emails in Outlook, you can right click on the folder you wish to upload, and hit -> Copy folder. Once the folder is copied, you can move those emails to GMail, so your original emails will still be stored in Outlook.
This could take a while, especially if you have large emails. I tried selecting all the emails, and moved them to gmail, and my Outlook hung, so I did them one batch at a time.
You can comment here, if you face any problems.

Pretty neat bro - good and easy
If I do that with all my archives, I’m gonna run out of GMAIL space hahahah!