Wierd expression

Hello, Fiasco, Welcome to the Forums!
I moved your post to this section, I think you'll get an answer more quickly!
PS: it's weird

Thank you for your effort, but that's not exactly the explanation I'm looking for. I've already know the one meaning of 'penny-loafered', that is the one you mentioned, as you might have noticed I wrote I'm looking for it's meaning as in the expression 'penny-loafered self ' describing, from what I managed to deduce, someone who is bad or something like that. I've searched all the Internet and found it decribing ,for example politicians, but I didn't grasp the exact essence of that expression... I don't think it was meant to express that someone's self is 'low, leather step-in shoes', don't you think?

Anyway, thank you.
I'll still wait... maybe there is someone who knows that expression...

I do apologise for misinterpreting your first post, and I hope you won't mind if I try again.

Here is a definition from a site selling penny loafers (bear with me, I'm not going to define the shoe!)

The classic penny loafer speaks of someone tied to tradition yet open to learning and moving forward with the changing times. Frequently seen on college campuses, the loafer graduates to the business world with a self-assured stride.

I looked up "penny loafered" and got lots of hits where the expression was used, mostly in a slightly derogatory sense, as in the example you give.

I have the impression that "penny-loafered" is a term for an ambitious, middle class and probably self-seeking person. Such people are often associated with conspicuous consumption - they wear the "right type" of clothes, eat and drink at fashionable places, and usually have jobs or businesses which involve making a lot of money, perhaps from other people. (I notice that lawyers and politicians are often referred to as "penny-loafered")

In England in the 80's we used to speak of in a derogatory tone of "yuppies (Young Upwardly Mobile Professionals)

Yuppie - "A young city or suburban resident with a well-paid professional job and an affluent lifestyle" (dictionary.com)

I think penny-loafer wearers are much the same, but not defined by age, as all ages wear them, from preppies to retired middle class men and women.

Hope this helps a bit more in the context of your reading.

Well, he certainly has a sense of his own importance, and may be inclined to look down on others. He may or may not be over-ambitious, but equally may come from a wealthy background, and have genuine power, but I think you're getting the picture.