The Urban Dictionary is probably most laconic about it, defining 'hip' as 'Cooler than cool, the pinnacle of what is "it". Beyond all trends and conventional coolness'. To explain the meaning we need to look back to the Slave Trade era times when it is believed to arrive in America from West Africa and formed a part of the lexicon used by former Africans in their new homeland. It had entered mainstream English in the 1960s as a part of the Beatnik subculture. Today it means 'Being modern, Informed, up to date, fashionable, contemporary, and relevant'. E.g.: 'Fort Greene is an incredibly hip, up and coming area in Brooklyn that attracts hipsters, artists, and foodies'. Looks like 'hip' and 'hipster' are related words but thanks to its respectable age 'hip' cannot be short for the much younger 'hipster'.