Here is a simple version. Let's say you have two options, one is with the strike of 100% and IV of 20%, the other one is struck at 90% and has IV of 23%. So that's a skew of 3% which means that the market expects that if the underlying goes from 100% to 90% over the life of these options, it's going to realize an average vol of 21.5%. So, if you are delta hedging and it follows that path, if volatility is higher then 21.5% you will lose money and if volatility is lower, you will make money.
In real life, however, this all would be complicated by a variety of facts (your delta model, hedging frequency, hedging vol etc).
In real life, however, this all would be complicated by a variety of facts (your delta model, hedging frequency, hedging vol etc).