Can't sync iPhone to Outlook

How are you attempting to sync it currently?

If you haven't, try these steps.
1. Connect iPhone to your computer via usb cable
2. Open iTunes
3. Click Devices > Your iPhone
4. Click the Info tab
5. Under Contacts, click the Sync contacts from and then click Outlook, click apply
 
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I use Outlook as well and synchronize it with my iPhone. For this purpose I use Google account and a program called Sync2. It can be used to sync iPhone with Outlook via Google account.
 
If you have a gmail account and ran Thunderbird, the calendar feature syncs without PC connection to all devices with access to that gmail account
 
Configure iTunes to Sync Outlook Contacts, Calendars and Notes

1.Click the "Start" menu, select "Program Files" and click "iTunes." iTunes will open on your computer.
2.Connect your iPhone to your computer using the device's USB connector cable. Wait for your iPhone to establish a connection with your computer. Once the device has successfully connected, your device will appear beneath "Devices" on the left side of the iTunes program window.
3.Click the name of your device. A summary of the contents of your device will appear on the right side of the iTunes window.
4.Click the "Info" tab above the summary of your iPhone's contents. Click to check the box next to "Sync Contacts with" and select "Outlook" in the drop-down menu.
5.Scroll down and click to check the box next to "Sync Calendars with" and select "Outlook" from the drop-down menu. Click to check the box next to "Do not sync events older than" and type the number of days you want to restrict your calendar history to displaying.
6.Scroll down and click to check the box next to "Sync Mail Accounts from" and select "Outlook" from the drop-down menu. Type your email address in the text field.
7.Scroll down and click to check the box next to "Sync notes with" and select "Outlook" from the drop-down menu.
8.Click the "Sync" button at the bottom of the iTunes window. This will sync your Outlook contacts, calendars and notes with your iPhone, but in order to send and receive email messages from your Outlook account on your iPhone, you need to configure your iPhone's Mail application settings.

Configure iPhone to Send and Receive Outlook Messages
1.Turn on your iPhone and enter the passcode if you have one.
2.Tap the "Settings" app.
3.Tap "Mail, Contacts, Calendars" from the menu.
4.Tap "Add Account" and then tap your email account provider.
5.Type the login information into the corresponding text fields and tap "Next."
6.Tap "Save" to finalize the setup of the email account on your iPhone's Mail app.
Items you will need
 
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