PARENTING FAIL: Who Taught Millennials How To Dress Up?

MillenialThe older I get, the more I slowly morph into my father.  The shocking part about that transition is; I’m perfectly happy with the change.  My father was a bad ass, no bullshit kind of guy.  He spent 23 years as a Police Officer in the New York City Police Department. The majority of his time with the NYPD, he was assigned to Brooklyn precincts.  As a young no-nothing dickhead, I didn’t realize how important everything he was teaching me really was.  I’m not talking about my morals or values, that goes without saying.  Also, those weren’t taught to me, they were expectations placed on me by my father.

My father taught me things like; a firm handshake is the sign of a gentleman.  He taught me how to tie and wear a neck tie.  You may read this and think that I’m representing the handshake and neck tie lessons as trivial; quite the contrary.  Those two lessons have had a profound impact on my life in terms of my success and financial stability.  I’m going to share some of the basics of wearing a suit or business casual outfit that are absolute musts.  I see too many millennials that look like 5 pounds of shit in a 1 pound bag and it makes me crazy.  Also, your weight is not an excuse to look like a soup sandwich; get it together regardless of your size.

So, you’ve been invited to a wedding, you’re going on an important job interview, you want to impress your woman with a fancy night out – whatever the reason, pay attention.  Do NOT expect to walk into a store and walk out with a perfect fitting suit.  You can get a suit in stores like Kohl’s that are sold as individual pieces.  Other than an absolutely emergency, I can’t condone this behavior.  That doesn’t mean you need to spend a ton of money having a custom suit made.  Stores like Jos. A Banks or Men’s Warehouse have some decent quality suits for reasonable prices.  But back to my original point, suits MUST be tailored.  Tailoring takes time (in most cases, two weeks or more).  It’s important that you factor the cost of tailoring into your suit budget.

If you’re trying on the suit and thinking, “maybe I don’t need to have it tailored, it fits well!” Stop.  Even if your girlfriend is saying, “I think it looks nice.” It doesn’t, you need tailoring.  If you decide otherwise, you’re going to spend hundreds of dollars on a suit and look ridiculous when the sleeves on your jacket come down to your thumb.  Yes, that’s ridiculous.

My last point along these lines is the shirt.  You’re going to have to ask the tailor or the salesman at the store to measure you for you proper shirt size.  Wearing a shirt under a jacket is much different than throwing on a J-Crew button down.  It needs to be form fitting so that it doesn’t bunch up along the waist and should when you put your jacket on.

Pockets Get Buttoned

Guys – you’re killing me with this one.  Button holes on the back pockets of your pants were placed there to hold the pocket closed with a sewn on button!  It’s not an aesthetic!  Take the time and do it right.  Fill that hole!



You’re A Dickhead If You Do This.

I’m not going to sugarcoat this one; if you button the top button on your dress shirt, you’re a dickhead.  Top buttons get closed only if you’re wearing a tie.




TieTie Length

Tie length is super important, but millennials use so much of the tie to form a big fat knot, that the tie length is ridiculously short.

The ideal tie length brings the tip of the tie to the center of your belt.






gigGig Line

The gig line is the line made by the alignment of your button-down shirt, your belt buckle, and your pants fly. Make sure they are all in a straight line.







Yes, there is a right and wrong way to wear a belt.  Men should be feeding their belt in from the your left hand side – behind your back – around your right hand side.  Feeding it the other way is how a woman wears a belt.  If you’re doing it wrong, congratulations, Sally.

Also, on the topic of belts; wear one!  If you’re not wearing suspenders, a belt is absolutely mandatory.  Should you elect to not follow my advice, I assure you – you will look like a giant slopopotomus.


short sleeveShort Sleeve Shirts with a Tie

If you’re doing, or thinking about doing this.  You’re a lost cause.  Move on.








I’m going to make this easy for you.  Go, they have great looking ties at reasonable prices.  Stick with dark colors here though.  Stay away from bright colors or wacky patters; you’re a man not a cheerleader.  Blue and red are classic tie colors and safe bets.

Along the same lines, get a tie bar.  Tie bars are great accessories and really put a suit together.  Also, they’re functional in that they keep your tie in place and keep it from whipping you in the face when the wind blow.

Placement of a tie bar is important also.  The most common faux pa is to place the bar towards the bottom of the tie.  Don’t do that.  The tie bar should be place in one of two places; even with your nipples or even with the top of your breast pocket.  You chose.

white socksShoes

Lets get this out of the way up front, it’s never ok to wear sneakers with a suit.  Get a pair of classic leather shoes when you dress up.  You don’t have to spend an arm and a leg on your shoes either.  Spend some time online to see what the expensive brands are doing, in terms of style.  Then head to your nearest department store for a good looking pair of knock offs.  You’re set!

I’m going to group socks in with this point.  First rule, never, ever, ever wear WHITE SOCKS with a suit.  Even if you don’t think anyone can see your socks because your pants cover them.  Rest assured, everyone will see them when you sit down.

I tried to stay away from style in this article because, I’m certainly no fashionista, and to each his own.  However, if you want to be thought of as a man, or better, a gentleman, these points are the bare minimum.  If you’re interested in being a tool and looking like a 5 year old playing dress up, well.. keep doing what you’re doing.  You’re nailing it.


James D'Arcy

James D'Arcy

Jim is a senior executive for a private security contractor. He has been responsible for, among things, the protection of assets, people and property for several multi-billion dollar companies. Jim can be reached at

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