Since I have recently embarked on this 25th year of life I feel I am now able to say, "RVMVMBVR WHVN WV WVRV YOUNG?" While replacing the "e's" with "v's" for no apparent reason whatsoever. I also can wear jeans with holes in them to my full-time job, I guess that makes my day job pretty cool huh? I chose wisely.
Truth is - you can really wear anything you want anywhere, as long as it's put together. Now let's not take it to extremes. Wearing a prom dress to Superman's Fortress of Solitude, or a Moncler jacket to a Jamaican Beach would be at the very least, vexatious. I have always been a massive fan of pairing high/low fashion. Most of the time that is in reference to wearing Prada with Target, but I think it works here as well. On it's own the commonly referenced, "bro tank", would look like I was walking straight into Fraturday Night. However, paired with the satin black vest and leather/suede booties - the look is put together, completely work appropriate AND fun.
So give the high/low fashion thing a try! In the wise words of Dr. Suess,