Outlook.com (formerly Hotmail and Windows Live Mail) does not allow users to add photos to the contacts listed on their People page as of September 2014. Although some alternative email services, such as Gmail, permit you to upload photos representing your contacts, in Outlook.com you can only add a photo to your own account's profile. When you add a photo of yourself, other Outlook.com users will see it next to your information on their People page. Likewise, you will see photos next to any Outlook.com People contact who has added a profile photo.
Add a Photo to Your Profile
Log in to Outlook.com, click your name in the top-right corner of the page and then click "Edit Profile" to access your profile. On the Profile page, click the "Change Picture” link on the left. Click the "Choose File" button when it appears, navigate to find the photo you'd like to use and click "Open." When the photo appears in the large box on the Profile page, drag the photo to position it where you like and, if necessary, click and drag the edges of the box to adjust the photo's size. When you're done, click the "Save" button.
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