It’s not about politics.

Tie: How long is too long?

It’s not about right and wrong. It’s about style. I’m not even going to go into the hair (though it seems logical if your hair looks like the underside of a goat, then a close-crop is an obvious answer). It’s about clothes. Clothes maketh the man. So they say.

Comedian and TV host Bill Maher referred to Trump as a 50s guy, and hopefully the last 50s guy to run for president (this was of course pre-November 2016). While many of Donald J. Trump’s preoccupations may date back to the 1950s, his clothes definitely don’t. They are 80s all over. The big boxy suit. The antithesis of classic Italian-styling (which in the 2010s at last seems to have won the suit wars). Red ties worn too long. A tie should not hang past your belt buckle. The baseball cap and shirt sleeves when trying to dress down.

The business world like other areas of life comes inherent with certain expectations, but when does an outfit become a uniform? And when does a uniform make you a prisoner?

I decided to come up with a few solutions.

Danny Kastner

Some fashion tweaks for President Trump (or any man) stuck in a style rut. But I soon realized the scope of the task was vast and multi-faceted, so enlisted the assistance of an elite panel of experts, men about town, men who knew a thing or two about fashion, men whom I knew would think out of the box.

First of all, Danny the Hipster from Apprentice Season 3—famed for his colorful suits and tendency to whip out a guitar at the drop of a hat, and entertain the housemates with song. Fired for his colorful suits and tendency to whip out a guitar… well you get the picture.

Then we have Rocco Siffredi, art-house star of Catherine Breillat film’s Romance, and Anatomy of Hell—and over 1300 pornographic movies.

Rocco Siffredi

Finally, John Hollister*, Jr, great-great grandson of the famed founder of Hollister Co, surf lifestyle clothing brand brought to you by Abercrombie & Fitch. Gentlemen, welcome. Your thoughts?

Danny: “Well, I’ve written a little number to sum up my ideas, so let me just sing it to you.” (Sounds of fumbling with instrument). “Kinda hum along if you like.”

“My name is Donald Trump,
And I’m stylish you see
All my clothes come
From 1983.

“Daddy you could be more up to date
Ivanka said to me
So tomorrow I’m gonna get
a suit of burgundy.”

“Burgundy suit. Green suit. Purple suit. You can’t go wrong man.”

Great, thanks Danny, wonderful song. Up there with Imagine. Rocco?

Rocco: “I know Donald loves my work. He looks up to me. He learned how to grab pussy from watching my movies. But, maybe he is slow learner. I only receive compliments myself.”


“Oh clothes. A suit. Italian-styled of course. Fitting. Black. Pinstripe, maybe. A fedora. That’s what I choose to wear. When I’m not working—I mostly work naked.”

Sure, Rocco. Whatever. And Mr. John Hollister, Jr?

John Hollister, Jr

John Hollister, Jr: “I’m just gonna just say one word. Cargobeachshorts. President Trump needs to get away from Washington and NYC and come out to SoCal. Do a little surfing. Hang out at Venice beach, catch some rays and get a great all over body tan. Goodbye tan bed orange. Beyond that. Casual tweed. A smart bow tie. Start smoking a cigar.”

It’s not about Donald J. Trump. Not really.

Anyone can hold on to a trend too long. Male or female. Men have a tendency to find one style of clothing, usually in their mid-20s, just out of university. In those glory years, they find the “perfect” outfit, settle and spend the rest of their lives wearing shades of this one outfit. Rarely do they move beyond this safety net that becomes like a uniform and a straitjacket in one. Yet reinvention, is a vital part of growth. If you’re 20 you shouldn’t still be dressing like you were 15. Just because you are post-50 doesn’t mean you shouldn’t reinvent your style. Your wardrobe should reflect you now, not you 5, 10 or 20 years ago. Yes, for a moment, consider purple, consider tweed, consider crazily stripped socks. Have a Grande White Mocha with that.

It’s never too late to be a hipster.

Age is no barrier to looking awesome

*Yes, I know John Hollister is fictitious, but so is this whole article.