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I would love to say hipsters are cooler, but I have to say the jock is cooler sadly. Hipsters know a thing or two about cool, but cooler bourgeois (look it up) people are generally cooler than otherwise. Being non-bourgeois to be cool is like taking out a loan to be cool yaknowhatimsayin. This probably makes the jocks cooler from an objective standpoint. That's just me though.
The term "hipster" makes me sad for the human race. If you like sweaters, skinny jeans, glasses, and goatees, then by all means suit them if you want. Most athletes work their ass of to achieve "coolness". And I've never met a dickhead jock. Most are fairly nice and hard working individuals while "hipsters" are wanabe fags.
I don't like the presumption that I don't know what 'bourgeois' means, OP.
Also, where's the option for 'neither'?
In this hypothetical scenario, we're comparing a stereotype to another stereotype, both of which are usually used in a pejorative way. There's no "objective standpoint" because they're not objective classifications. I can think of cool hipsters and lame hipsters. I can think of cool jocks and lame jocks (although the jock stereotype is more an American thing).
The jock has to earn their coolness by being good at whatever sport they play. Sometimes the 'coolness' they are given is much undeserved, regardless how athletically talented they are (dickheads and whatnot). Other times, they can be the type of person that is good at mostly everything they do and everybody gets along with them and wants to be their friend.
The hipster has to earn their coolness in a different way. Most of the time it's more of an 'adopted coolness' versus the kind of 'natural coolness' the jock has. Oftentimes, the hipster may think that they are super cool and stuff, but in actuality, they are really douchebags that nobody really likes. Snoody and stuck up those ones are... To me, for a hipster to really be cool, they have to have a type of eccentricity about them. The types of people who are naturally different. They aren't trying to be different, they just are. They always have been and always will be. Not sure if you'd label those types of people as 'hipsters' though. The word 'hipster' often has a negative connotation.
Overall though, the coolness of any particular person depends on that person specifically, not their generic stereotype someone labels them with.