Trends are only truly cool when they’re not quite cool yet.  And by the time they are in style, they’re pretty much going out of style.

Recognizing the hilariousness of how in many offices in America, it is standard that everyone dresses professionally Monday through Thursday, but on Friday, everyone goes casual with jeans and often t-shirts, at the beginning of the summer I decided to start making Thursday a “buffer” day for how I dress in the office, encouraging everyone else to participate.  How do you transition from khakis and dress shirts to jeans and t-shirts?  Hawaiian shirts.

They are button-down shirts with collars.  Perfect, tacky transition.  At first, only one other coworker would join me in Hawaiian Shirt Thursday.  But then, if for no other reason they felt like they were missing out on something cool, one by one, others began joining us.  By the end of the summer, I had half of the office on my side.  Some people dug through their closets to find the shirt; some actually went out and bought one.  And now, even in autumn, many of us are keeping the tradition going.

Of course, this isn’t the first trend I’ve started at work.  In an effort to make sure I was drinking enough water everyday, I went to Whole Foods and bought a glass Voss water bottle that I refill several times throughout the day.  At first, coworkers joked with me, “Isn’t it a little early in the day for vodka?”  By now though, several of them have privately approached me to ask where they could get a water bottle like that.  And sure enough, the glass Voss water bottle is no longer weird in my office, but instead it’s the norm.

But the irony with trendsetting is that by successfully coming up with an original and unpopular idea, it eventually becomes unoriginal and popular.  Prime example: Crocs.  For the last couple of years, I’ve looked on from a distance at the weird plastic rainbow colored Birkenstock rip-offs.  They were so trendy.  You’d see moms and their kids out at the mall, all wearing Crocs.  Even though I wanted some, I refused to buy them.  Because they were too cool at the time.

However, this week I came to a realization.  The Birkenstocks I have been wearing were given to me by my parents Christmas 1999.  I had already paid $35 five years ago to have them resoled.  It was time for me to either have them repaired again, or pay $110 for new ones.  Or… pay $30 for some brown Crocs.

To entertain the idea of buying Crocs, I checked around Cool Springs during my lunch breaks while riding my mountain bike instead of driving (another office trend I’ve been trying to start since April), but sure enough, I had trouble finding any Crocs for sale.  Eventually, some girls behind the counter at a Hallmark told me to check out the Croc stand across from Fossil in the mall.

Needless to say, with yesterday being Thursday, I wore my Hawaiian shirt, with Crocs, while drinking water from a Voss water bottle.  And boy was I cool.  Yet I wouldn’t have been caught wearing Crocs if they were still trendy.  The trend of wearing Crocs is over; which is why it was more difficult than I had imagined to find them.  I’m not saying that Crocs aren’t cool anymore; they’re just no longer a fad.

And so an important rule for a trendsetter is to not get involved in a trend that is overly popular.  But once a trend is over, then it’s “game on” to participate.  Some fads, after their prime, become an outdated, yet timeless classic.  Like Hawaiian shirts.  And Chuck Taylor’s.  And the wondrous Rubik’s Cube.  WWWD bracelets?  Not so much.