My family has been extremely fortunate financially and consequently my income has always been far greater that it 'should' be. I have been receiving share dividends since I was literally like 5 and due to where I live I could walk to all my retail jobs and employers loved me because if someone was sick they could call me and I could be there in 15 mins.
Thus, I rarely pay for transport, no gym membership (family one), I receive lots of free cosmetics, I don't drink coffee or alcohol, I NEVER eat out and I still fit the clothes I wore as a teenager so my expenses are lower than my contemporaries along with a greater income.
In my experience things work together - you shop somewhere and build a relationship with the staff so they contact you prior to sales, give you discounts, refund when they shouldn't. You need to spend money to save money if that makes sense.