Front combines email, social, and chat into one inbox, which Outlook does not, but only makes sense if handling multiple channels is central to your team.
Only use Outlook if you are locked into Microsoft 365 and do not need to manage support from social or chat alongside email.
If your team's main support workflow relies on juggling email, social messages, and chat all in one place, Front is built for that reality. It actually pulls everything into a single inbox, letting you manage those fragmented channels without losing your mind. But if email is your main thing and you aren't really living in your DMs or chat apps for support, Front's biggest features won't matter, and it just adds complexity.
Outlook is a straightforward all-in-one email and calendar tool, especially if you're already deep into Microsoft 365. It's reliable for standard email and calendar needs, but it's not designed to handle support spread across multiple channels. If your workflow is just email (and especially if you're at a company locked into Microsoft tools), Outlook does the job.
So if you genuinely need to support customers everywhere, email, chat, social, Front is the only one here built for that. If you just need solid email and calendar, Outlook is fine, especially for enterprise teams already using Microsoft. Don't pick Front unless you're committed to multi-channel support as your core workflow. Pick Outlook if all you care about is standard email and calendar and you're already using Microsoft 365.