Good point! What I ended up doing is using VBA date function to add the dates to the listbox when the user form initialized.
Private Sub UserForm_Initialize()

With shipdatelist
    For i = 0 To 24
    .AddItem Format(DateAdd("m", i, Date), "mmm-yyyy")
    Next i
End With
With orderdatelist
    For i = 0 To 24
    .AddItem Format(DateAdd("m", i, Date), "mmm-yyyy")
    Next i
End With

End Sub
If you want to add days instead of month then change "m" to "d".