A soft squishy saddle may feel good for the first few miles but your sit bones will sink into it, transferring the stress to your soft tissues. Your saddle area will become sweaty and then you will get saddle sores caused by friction on damp skin in the perineal and gluteal areas. Worse, the sweaty environment will encourage bacteria to grow, causing infections and eventually boils.
Much better to get a well-shaped but firm saddle (Charge Spoon is excellent) and make sure you've got it set up right, which means:
Correct angle.
Correct height.
Correct position on the rails and hence distance from the bars.
Correct height differential with the bars.
Correctly set up, a good saddle will "cup" your sit bones and carry your weight in the way Nature intended.
On shorts pads, unfortunately the cycle clothing industry has decided that we all need soft squishy pads but these are a mistake in the long run for the same reason. The pad is supposed to wick away moisture and prevent the shorts from creasing and folding, not provide thick spongey padding.My most comfortable shorts are my 3/4 dhb Roubaix bibs, which have a thin, firm pad.
Brooks saddles work by stretching to match the shape of the rider, which is why they are provided with a tightening bolt. They are fine if you plan on avoiding rain but they are damned heavy and IMO a modern plastic saddle does as good a job for less weight and expense and in wet or dry weather.