Yes you can. An error will be thrown if the existing values have a larger size than the new datatype. See below.
koen>create table things (name VARCHAR2(100));
Table THINGS created.
koen>insert into things(name) values ('Car');
1 row inserted.
koen>alter table things modify name VARCHAR2(5);
Table THINGS altered.
koen>alter table things modify name VARCHAR2(2);
Error starting at line : 1 in command -
alter table things modify name VARCHAR2(2)
Error report -
ORA-01441: cannot decrease column length because some value is too big
01441. 00000 - "cannot decrease column length because some value is too big"
*Cause:
*Action:
koen>