How can a person have looks without confidence? If I were 6'4", 230 lbs, and had big muscles, all I would need to do is look in the mirror every morning to get the confidence I would need.
I actually have a case study that opposes this.
I had a very good friend when I was working at the gym, he was around 6'7", white guy in the Air Force, and made decent money. Was in pretty good shape somewhere between buff and lean, had all his hair, and was a really friendly all-around person.
The guy could NOT properly talk to and flirt with women he was interested in unless he was WASTED. Now he wasn't a nervous wreck around women, but he couldn't make moves unless he had plenty of liquid courage. One of the front desk workers with us was a really hot college girl who had a crush on him, and even when told this, he would never ask her out. I don't remember how it came about but they went out for drinks or a date once and he had to get plastered to drum up the confidence to go in for a kiss, and unfortunately, that's as far as it ever went.
He's currently married to a very average-looking chick that I'm not sure how he met, but he seems happy so all the best to him.
As for a response to OP's question: like many things when it comes to women, I think it's a good gesture unless it's expected. Kinda like how if I'm at a bar having a good time with a girl and she buys me a drink I might buy her one, but if I go up to some random and one of the first things she asks if I'm going to buy her or her friends a drink...immediately no.
Though I will say the guy is definitely overdoing it if he does this EVERY TIME, like for mundane stuff where you're just leaving the house and not having some sort of date night.