First of all, the slang "hypebeast" may be defined by Urban Dictionary as : "A person who follows a trend to be cool or in style. A person who wears what is hyped up." Basically, "hypebeast" represent the type of guy who is interested in the newest sneakers, clothing or accessories from top brands like: Nike,Air Jordan, Supreme, Bape , Palace, Vans, adidas Originals, Louis Vuitton, Huf etc.
The main reason for collecting this expensive stuff is doing what's in vogue in order to impress other people or resell. However, some people argue that they use parents or older siblings money. There are also rich peoples that afford to buy this expensive clothing by their cash flow or reselling. People that resell usually "snipe" low prices on this products and sell them further, of course, with a bigger price ( For example, the new Louis Vuiton x Supreme hoodie is expected to be reselled from 2000 $ up to 20000$).
Most of the rappers can be considered hypebeasts. Some examples are : Kanye West (he is partner with adidas Originals on "Yeezy" sneakers that are so trendy) , DJ Khaled , G-Eazy, Migos etc. The mains promoters of this culture are Hypebeast magazine or Complex YouTube channel which has a series on YouTube " x Goes Sneaker Shopping with Complex" where x means a famous personality, featuring G-Eazy, 50 Cent, Macklemore, Logic, Migos and many others.
Hypebeasts are also associated with skateboarders because the most hyped brands are skateboarding brands: Supreme,Palace,Nike SB, Trasher. These brands are highly fashionable.
In conclusion, I think it is worth to be a hypebeast only if you resell most of the products and keeping only the things you really like.