Start by creating a spreadsheet with the following headers in any order. Here's a sample:
Subject
Start Date
Start Time
End Date
End Time
All Day
Description
Location
UID
Busy Status
English 101
01/30/2019
9:00am
01/30/2019
9:50am
FALSE
With professor Smith
LARTS 404
abc@abc.com
BUSY
Group Process Day
02/02/2019
02/02/2019
TRUE
Oak Glen Hall
def@def.com
BUSY
Meet and Greet
02/04/2019
8:00am
02/05/2019
5:00pm
FALSE
Meeting others all day long for two days
ghi@ghi.com
FREE
For the Busy Status column you can write any of the following: FREE, WORKINGELSEWHERE, TENTATIVE, BUSY, AWAY
Then export it as a CSV file (Download this sample)
Upload the csv file using "Choose File" above, and hit "Generate & Download" to get the iCal ics file
Then you can simply import the ics file into outlook:
