By the way, this is a good question. It's naive to say that you should just order what you want. Clearly there's a big spectrum between totally living to impress others and just saying f*** it.
Just like you wouldn't wear a tie-dyed tee to a job interview, you wouldn't order a Jaeger bomb in the clubhouse after golfing with the 45 year-old managing director at your bank.
If you tried to order a college mixed drink at an opera intermission, you'd get blank stares.
What if you were on a date with a woman 7 years older than you? You wouldn't want to draw more attention to the age difference through your drink selection.
Even beyond the age issue, there's the simple issue of appropriateness for given situations. You wouldn't order a pina colada at a steakhouse with red leather booths.
Granted, you shouldn't drink something you don't like, just to impress other people. Nevertheless, it pays to be aware of how your actions can be perceived.
An anecdote: my brother was at the bar after work. He orders a Manhattan, and his boss's boss says something to the effect of, "now that's a man's drink." The strike up a conversation for 5 minutes or so, and the next day he's been put on an exciting new project.