Making specifically new clothes do that wouldn't be good, since right now you can make & wear any outfit you want, without having to choose between the one you like in terms of looks and the one that gives you a buff. So maybe make it something you can add to your current outfit with a sewing machine?
If you pass out from exhaustion or 2 am hitting you dont lose items, just 10% of your money, though you can't lose more than a 1000g and wake up with less energy. You only lose items if you "die" from taking too much damage