Dapper

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"Very handsome!" said the lady at the tailors. I was bursting with confidence having just picked up my first custom-tailored suit. I stepped out into the promenade deciding to wear it home. It was 75 degrees and perfectly sunny.

Within seconds of walking, I noticed something that had never occurred to me before. EVERY single woman (including grandmas) was gawking at me. Now let's be real. I'm a handsome guy, cute even. Add some wit, charm, glasses, a tuxedo and let me woo you with words now I'm a solid eight for sure. Both confused and elated I continued to indulge having my confidence serenaded with attention. "I should have gotten my suits tailored sooner!" I thought.

My shoelace came undone. I crouched to fix it, and then I saw...him. Walking in perfect stride behind me was a 6-foot male Adonis. Let's call him Chuck. Chuck too had a perfectly tailored navy suit, but unlike myself, he had an aura about him. It was in the details. Polished brown oxfords, slim knit tie, white pocket square, silver tie click, large rimmed glassed, perfectly groomed hair, a Saks Fifth Avenue bag with flowers in the right hand, and a Kurt Vonnegut book in the left. Simply put, Chuck was muy dapper. 

Having never forgotten what it was like to walk in Chucks shoes in the 3 minutes between the tailors and my shoelace coming undone, I've learned the following about being dapper. Dapper is more than clothes, it's a set of principles that guide your actions. Note: Ladies, apologies if it's geared towards men, but please do feel free to share with your soon to be dapper man.

  • Simplicity in your wardrobe is the ultimate form of sophistication.
  • Rebel from business casual. Burn your khakis and wear a suit.
  • Have a cobbler, a tailor, and a barber.
    • It's better if old men cut your hair.
    • Cobblers will save your shoes.
    • Get your suits tailored.
  • Own a tuxedo before the age of 30, then stay that size through your 30's.
  • No clip ons.
  • 90% of dressing well is having the right fit.
  • Never take an ex back. She tried to do better and is settling with you.
  • Date women outside your social circle. 
  • When in doubt kiss the girl.
  • Don't use the word "closure" or ever expect it in real life.
  • Find a Times New Roman in the streets and a Wingdings in the sheets. She exists.
  • Eating out alone can be magnificent. Find a place where you can sit at the bar.
  • Tip more than you should.
  • Be a regular at more than one bar.
  • When a bartender buys you a round, tip double.
  • Learn to bartend, but keep it simple.
  • Drink outdoors. And during the day. And sometimes by yourself.
  • You cannot have a love affair with whiskey because whisky will never love you back.
  • If you are wittier than you are handsome, avoid loud clubs.
  • Become your own curator of information.
  • Read more. It allows you to borrow someone else's brain.
  • The best public restrooms are in hotels.
  • If you believe in evolution, then you should know something about how it works. Approach life similarly.
  • No selfies. Aspire to experience photo-worthy moments in the company of beautiful women.
  • Take more pictures. With a camera.
  • There is always another level. Be grateful knowing that you are still better off than most who have ever lived.
  • Do not use an electric razor.
  • Throw parties. Pay for the liquor and food.
  • Always bring a bottle of something to the party.
  • Measure yourself only against your previous self.
  • When you admire the work of artists or writers, tell them. Then spend money to acquire their work.
  • Staying angry is a waste of time.
  • Stop talking about where you went to college.
  • No one cares if you are offended, so stop it.
  • Don't gamble if losing $100 is going to piss you off.
  • Always carry cash.
  • You use your cell phone too often and at the wrong moments.