Twelve Style Tips for Gentlemen

Twelve Style Tips for Gentlemen

1. No khaki pants.  Especially with cuffs on the bottom.  In fact, no pants at all with cuffs on the bottom.  Only wear Dockers khakis if you want to ensure your bloodline dies with your present generation or if you are going for the lumpy dad effect.  Add a blackberry holster to make the look complete in that case.  For the rest of us, no khakis!
2. No polo shirts.  No mortal man looks good in a polo shirt, even if he is on the back of a lumbering horse with a mallet in his hand.  The only time I’ve ever seen a polo shirt look good on a man was the last time Tiger Woods wore his red polo shirt on the final holes of the Masters when he won by 14 strokes.  I think that was back in 1997.
3. No baseball caps.  Unless you are Russell Simmons- then you can get away with it. Or if you are Derek Jeter on the field at Yankee Stadium. Otherwise you look like a “bro.”  Speaking of “bros”…
4. No oversized sports team jerseys.  Unless you are on the ice pounding someone against the boards, no hockey jerseys. A gentleman does not dress like this.  Unless you have one of those plastic hats that holds two beers with tubes to your mouth and you are tailgating in the parking lot of taxpayer-funded pro football stadium, just don’t do it.
5. No cheap watches.  This includes sporty marathon or G-shock watches.  No plastic watch should be on your wrist, unless you are screaming around on a fixie in a crit in Red Hook.  If you are running the Iron Man in Kona, you can wear an Iron Man plastic watch and look good. If you are showing up to a place of employment or are out for dinner, wear a real watch.  If you can’t afford one, save your pennies until you can afford one.  No watch is better than a crappy watch.
6. Details matter.  Wear decent socks with no holes in them.  They don’t have to be black.  Wear a decent belt. Add a pocket square instead of a tie.  Don’t try too hard with folding the pocket square- just fold it in quarters and have a little sprezzatura.
7. Get a suit that fits.  In fact, make sure all of your clothing fits.  I’ll take a $300 suit that fits well over a $3000 suit that bunches around the ankles and looks like it’s your dad’s suit.  Most men wear suit jackets that are too big.  Unless you’re an NBA player, get a suit that fits.
8. Wear decent underwear. Women know how important this is.  Why don’t we men?  Even if no one but you notices, you will feel better and walk the city streets with some pep in your step knowing that you aren’t wearing some worn-out tighty whiteys. Sorry, Fruit of the Loom is not a cool brand. I’m partial to 2Xist but it may just be a phase I’m going through.
9. Shine and take care of your shoes.  Shoes are tires on a racecar.  Get your shoes re-heeled.  Shine them weekly.  Successful people notice a man with poorly maintained shoes.  It implies lack of attention to detail and it ruins your whole look.
10. Plain t-shirts only.  I have violated this one with a vintage black Rush concert T-shirt or two, but that’s just nostalgia.  No “I’m with stupid” t-shirts or stupid slogans.  A plain black, grey or blue t-shirt looks classic.  Dress like a man.
11. Upgrade your wardrobe constantly.  Better, not more. Even men’s clothing styles do change over time.  Dispense with the misguided man rule that says you must wear an item of clothing until it is threadbare.  When you buy a new shirt, get rid of the oldest one in your closet. It’s also a great idea to buy a new shirt when going out with someone you’d like to impress.  The shirt will never look better than the first time it’s worn. It’s OK, really, you don’t have to still wear that 3” wide tie that you wore to prom.
12. Get a decent haircut.  Shave the hair off your neck between trips to the barber.  Nothing ruins a great haircut like hair growing down your neck like a neanderthal.