I generally disagree with the post. I think fountain pens and fancy notebooks are are a waste of time, though I've been through phases with both. For me - cheap pencils, cheap graph-paper, cheap folders, and a system to keep order.
There are often ways to be smart that don't involve spending money. There's an idea of people who have more money than sense who go with an expensive option because they're hoping that this increases their chance of getting the thing they will want/need.
I have a digital watch. It has a lap timer in it, and shows the full date, cost less than USD100 and far more reliable than the swiss watch I have.
But there is some truth in the article - if you're just frugal all the time out of principle it sends bad signals.
I also find strange the stigma attached to being a "loser".