Hey there!
This issue has been bothering me for a very long time now and i'm not sure if it's already addressed but: for me tucking a shirt or top into pants is not possible!
On my criminal character it doesnt work on any of my 5 outfit slots, so creating any clothes e.g. a long sleeved shirt tucked into high waist shorts is impossible to make, which leaves me, as a clothing designer, really frustrated being so limited in designs.
On my Enforcer it works on 3 of the 7 outfit slots I have and it's kind of bothering me that I have to switch or remove one outfit to wear another.
I've been trying to fix this by re-buying the items or using the "arrow"-buttons to switch the layering. It doesn't work. Also repairing the game or installing it freshly had no impact.
I can't tell if i'm the only one having this issue.
Thank you for taking your time reading this.