The softness of light is dependent on two things. The size of the source and the distance to the subject.
So if the umbrella is larger than the softbox, then yes, it will make it softer. (than the softbox alone)
There is also the quality of the light to be considered. Things like umbrellas and softboxes may not give you perfectly even light. There might be a hot spot in the centre, for example. This is why some softboxes have two diffusion panels.
So your plan of using both the softbox and the umbrella may improve the quality of the light as well as making it softer. Although, I believe the softness would be the same with the umbrella, soft box or not.
Now, you have to consider that using these modifiers does eat up some light...and if you start 'stacking' them, you may end up with less light than you need....but it will surely make your flash work harder, which eats up batteries and causes longer recharge times.