Dress for Success?

An old friend, who I hadn’t seen in ten years, showed me a picture of her two beautiful children.  As someone who has always done a nice job of putting herself together, she was quick to point out that the child pictured in the completely random outfit was dressed by her husband.  I laughed, as more often than not I am “that husband”.  My worst offenses are on school mornings when there is no time for a redo, and despite my wife’s ridicule our child usually heads out in my selection,  dressed quasi clown-like (except for the shoes, selected downstairs, which are thankfully not of the clown varietal).  It does beg an important parenting question – What is our responsibility when it comes to guiding the fashion choices made by our children?

To this day, I have a limited intuition around how to put an outfit together.  Sometimes I get it right for my kids, but their changing combinations confound me.  For my own person, I’ve completely outsourced the mental effort of looking respectable to my wife.  She has curated a series of shirts and pants that work together.  Much like my strategy in math classes throughout my youth, I’ve simply memorized the formulas.  I don’t need to understand, but I am aware.  At least no one laughs at me anymore, which was not always the case.


My second favorite outfit from childhood could be labeled “Don Johnson Formal“.  It was laughable.  Pin striped suspender pants, a canary yellow sport coat, a baby blue golf shirt partnered with a silver/skinny/square tie, all finished off with white mesh loafers.  The only thing missing was Tubbs.  Acquired at TJ Maxx, my mom just rolled with it, letting me commit fashion suicide.  I can only imagine the embarrassment and shame the family felt as they dined out for special occasions with a complete asshole (me, at least in appearance).

Acquired at TJ Maxx, my mom just rolled with it, letting me commit fashion suicide. 

My favorite outfit put Miami Vice to shame.  Remember Jams?  You probably think of the shorts, but there were also Jams shirts.  The outfit in question involved both.  The shirt had a deep blue base and was covered in a rainbow of flowers.  The shorts that “went” with the shirt were purple, but not a complementary purple.  They clashed like the houses of Lannister and Stark.  More alarming than my lack of understanding of the color wheel was the large thigh-sized “6” on the front right leg, mirrored by the large thigh-sized “9” on the front left leg.  For the life of me, I couldn’t understand why strangers pointed and laughed, and nudged their friends who proceeded to laugh, as I walked by them on the street.  It was only a few years later, in the cruel halls of middle school, that the reality of my endorsement for “69” at such a young age spiraled back to me in an instant.  One of my friends made a 69 joke.  I inquired.  I cringed.  The pointing, the laughing, the shame.  It was overwhelming.  The shorts never saw the light of day again.

dress for success

What’s up!?!? Kids’ fashion at its finest. The lone remaining pic of my “69” Jams.


Another friend recently shared the below picture with me.  This is a great family.  Their son, who is the “fashionable” one in the crew, reminded me so much of a younger me in my Jams uniform.  If he wants to roll around in a “snapback” hat (that’s what they call the flat brimmed hats these days) and an airbrushed t-shirt with Bonnie from Five Nights at Freddy’s, bless his heart.  He’ll either grow out of it or his parents will gently guide him.  As a bonus he will always have this picture to immortalize a unique period in his life.  That’s no small thing.

Kids' fashion

A modern version of me, dressed for success in his own special way.


So what responsibility do we have for our children in the fashion department?  Let them fail, or step in to assist?  Is it more important to “dress for success” or to let our kids be who they want to be…even if it kills us?

I think that the answer lies somewhere in the ether.  No one should let their kids wear “69” Jams, although I’m guessing (hoping, praying) my parents had no idea.  They did the right thing letting me clash and be Don Johnson.  There are other obvious times to step in, whether it be profanity or inappropriate on the sexy scale, but I’m a believer that we need to let our kids make their own choices.  In my case, they could realistically have a fashion sense that I simply don’t understand.

I did arrive at a point in college where I looked around the room at a party and realized that I was an awful dresser.  It was time for some sort of a fashion intervention.  On my next visit home I shared this revelation with my mom, who smiled and told me to get in the car.  Within an hour I had a new wardrobe.  It may not have been the hippest or priciest wardrobe on campus, but at least it matched and I now looked like an adult who an employer or someone from the opposite sex might consider as a potential option.

Whether we like it or not, appearance matters.  It gets you in the door and allows your amazing personality and character to shine through.  My mom was waiting for me to come around on my own, and chances are she wouldn’t have let me go much longer.  Hopefully my wife and I are wise enough to do the same if required.  Dress for success?  In due time, but definitely at some time.