Dear Hipster:

I find myself floating back and forth between Hipsterville and Broburg. There are times when the more intellectual and artistic ways of Hipsterville (even if they verge on pretension) appeal to me. But there are other times when the more relaxed (even if they verge on stultified) ways of Broville are hard to resist. Much like pimping, being hip all the time ain’t easy. Sometimes I just want to wear board shorts and flip-flops and not give a shit about irony, or my hair, or the origin of my morning coffee. Is that okay? Must I pledge allegiance to the flag of Hipsterville and burn the banner of Broburg? (If so, what do you think those two flags would look like?)

— Danny, Normal Heights

I picture the bro flag as two bro-lhouettes, hi-fiving in backwards baseball caps on a Solo cup–red field with crossed surfboards, pool cues, and bottles of weak beer.

Hipster flag’s a bit tougher, because no hipster would rally behind a known flag. While most critical types have observed that the majority of hipsters look and act more or less the same, hipster credo number one is “I am not a hipster,” so a hipster flag would scream Oxymoron!

To your more serious question (“Is that okay?”), I say, “Nay.”

Being cool is hard work and takes a serious commitment. One does not simply surf the day away, catch the MMA fight at Hooters, slam a few Buddy L’s, and then catch the closing set from a twee-tastic, suspender-clad Brawny ad of a man singing soft songs of love, loss, and the perils of an unflinching soul.

Don’t let your cool slip away, Danny, because it won’t come back without a fight.