Is it permissible for the man to go out wearing shorts?

All Perfect Praise is due to Allah, The Lord of The Worlds

It is permissible so long as his Awrah (private part), which is between his navel and knee, is covered. However, the regular wear traditions and modesty are to be observed. And Allah Knows Best

Is the son of the sister by breastfeeding considered a mahram in Islam, and is it permissible for a woman to go for Hajj with him?

Everything that is prohibited by lineage is also prohibited by breastfeeding. The son of the sister by breastfeeding is considered a mahram, just like the son of the sister by blood, and it is permissible for him to be her mahram for Hajj and Umrah. And Allah Knows Best.

I suffer from chronic asthma which requires ventoline inhale; which is an air causes the risperatory track/airways to expand. Am I permited to use it during the daylight of Ramadan? And does break one's fast? Noting that I can't go an entire day without using it?

Taking inhaler through the mouth or the nose breaks one's fast, because it is meant to reach the lungs which are part of the coelom. Therefore, whosoever use inhalers for couple of days is obliged to preserve his fasting and make up that day later. As for the ones the ones who need to use it every days are obliged to preserve his fast and feed a poor per day and the cost of feeding one poor is estimated (60) piasters for the year (1421AH). And Allah Knows Best.  

What is the ruling on going out wearing a long loose skirt with a long shirt that are neither tight nor revealing and without wearing any makeup?