I’ve seen this phrase used in ways I don’t understand, as in just walk up to the hottest chick there and look entitled. Or just read out your request and seem entitled.
Does this mean dress like you’re rich? A facial expression?
Does it mean act nonchalant?
Show her your Social Security check.
Well, as far as the ‘hottest chick’ scenario goes, it would mean look totally confident to the point of arrogance in regards to believing that you’re as hot as she is and you know it and she knows it so lets get away from all these ugly troglodytes and get down to what we both know we want and deserve. It means act as though your looks and ultra-high opinion of yourself ‘entitle’ you to be with the hottest chick, regardless of anything else.
Basically it means act like a shallow, narcissistic douchebag*!* 
Try this exercise:
At a bar, club or whatever, walk up to the most attractive woman you see (or think you can get with) and say “I’m [your name], let’s get out of here.”
Now I’m not saying this will actually work (in fact in probably won’t for any number of reasons). But there are a couple of important details to note:
I think your examples (I’ve never heard entitled used that way!), are prescribing an air of confidence. Because, for many things a timid, understated approach will fail to impress. Think job interview!
( Misapplication of the word entitled in my opinion. )
No, it means BEing awesome!
How does one do that? Bling out like you’re Kanye West? Wear a nautical hat and ascot?
Guys always think they can buy their way into getting women to like them. Bill Gates and Mark Zuckerberg are two of the richest men in the world and people still think they’re dorks.
Unless you actually ARE rich, you can’t “dress rich” enough to look like the sort of guy who is rich enough to attract the sort of girls who would be attracted to you because of your money. You just come across like some tool trying to look rich.
Plus depending on where you are and how you became “rich”, a lot of rich people dress like 14 year olds these days and a lot of people who dress “rich” are just middle-class sales guys.
Well, I have resting bitch face (Botox…for migraines, not for wrinkles) and look classically anglo-saxon. All I need is a Lady Mary Crawley costume and I’d be set.
Posture has a lot to do with it. If you’re sitting very erect on your sedan chair, for instance.
This will almost certainly work if [your name] is Ryan Gossling.
The phrasing is deliberately obscure to allow whomever you are taking the advice from to blame you when it doesn’t work.
I wear my top hat and a monocle, and stick my pinky out when I pick things up.
It’s obscure because it’s difficult to define, but people know it when they see it. As QuickSilver, pointed out, it’s believable when you see Ryan Gosling do it in a movie.
I feel like the art of actually picking up a woman IRL has become lost on todays younger generations. It’s too much with using social media, dating sites and apps like Tinder. That’s why there are so many “I’m a 28+ year old virgin, is that weird?” threads. In my day, there were always those guys in school who all the girls were really into. Usually the good looking football player or “cool” guy in the rock band or whatever. Does that not exist anymore?
Do people not know of someone from school or work or wherever who everyone is like “that guy can get any girl he wants”?
A beret and scarf, especially in warm weather.
That’s the classy way to do it.
You walked into the party
Like you were walking onto a yacht
Your hat strategically tipped below one eye
Your scarf, it was apricot
You had one eye in the mirror as
You watched yourself gavotte
And all the girls dreamed that they’d be your partner
99.999% of ALL advice on ALL subject matters, but especially “dating” advice, can be accurately thus described. ETA: Job interview “advice” too.
It’s a question of degree. There is a clear difference between merely acting confident and acting entitled (or arrogant). Not just in approaching women, but in all things.