“In Denmark, women approach men. Guys will only come up to you when they’re drunk. If the alcohol wears off, they’ll just walk away.” Rapha tells me during a private business dinner event at The Andaz on Wall St.

It was a fascinating conversation. (And a reminder that I’ve been living in the wrong country my entire life!)

Rapha, an American, was perplexed by how difficult it was to date in Denmark when she first arrived. Until she read a blog post about dating culture in Denmark.

It was ladies choice.

And alcohol is a must.

If you sat around as a woman waited for Danish men to approach you like American Men, you wouldn’t get far.

To succeed in dating in Denmark, you have to play the game the way the Danes do.

***

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HOODIE BY REIGNING CHAMP

WHY YOU PROBABLY SHOULDN’T WEAR A SUIT IF YOU’RE TRYING TO RAISE $50 MILLION DOLLARS

I’ve been meeting some of the most successful people in NYC – from 8-figure Entrepreneurs, to Realtors who sell some of the most expensive properties on the planet.

One thing I noticed with them is this:

They understand that there are games around them, and to succeed, they must play the game too.

“The worst thing you could do when going into a VC meeting is wear a suit.” TJ Parker, CEO of PillPack, who recently raised a $50 million dollar Series C tells me. “It’s kind of like dating, if you look like you’re trying too hard, they’re going to get turned off.”

“The Zuckerberg effect” I said.

“Yup” He replied.

Whether we like to admit it or not, we judge people by how they look before we get to know them.

Sure, your ideas, social skills and work ethic are what you’re selling.

But let’s not underestimate the power of first impressions.

Imagine going to visit a nutritionist for the first time.

Now imagine your nutritionist walks in and he was obese.

How would that affect your views on what they tell you, even if you know they’re saying all the right things?

“Stereotypes are seen as a necessary mechanism for making sense of information,” said David Amodio, an assistant professor of psychology at New York University. “If we look at a chair, we can categorize it quickly even though there are many different kinds of chairs out there.”

Dress culture in the VC world leans towards anti-suit. I can’t pinpoint an exact moment when that became the norm. I’ll take an educated guess when Facebook broke the Billions in valuation.

Of course, just because VCs culture is more casual doesn’t mean you should roll in like you’re 20 making a 7-11 run in a stained t-shirt after a Call of Duty bender.

“Some might say this is stupid, I’m going to wear whatever the f*&k I want to wear.” Roger Ehrenburg, founder of IA Ventures, says.

“To which I respond: fine. You should do what you think is right and reflects who you are. But if you go into a button-down-and-chinos firm in a ripped T-shirt, just acknowledge that you are creating a distinct impression that will unconsciously (or consciously) be noted. Part of that impression might be gee, these folks don’t really get us.” 

So what do you do?

You get smart about it.

***

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THE GAME OF DRESSING SMART

There’s a category of dressing that’s been making an appearance lately in magazine articles. It’s called dressing smart.

The funny thing is, nobody can give an accurate definition.

I’ll tell you what I tell my clients.

Smart dressing is all about adapting.

Smart Business Dress in San Francisco is different than Smart Business Dress New York. Just as Smart Casual Summers Dress in Italy differs from Smart Casual Summers Dress in Miami.

Smart dressing is combining your taste and knowledge with certain cultural norms.

That way you never are out style, but more important never out of place.

It’s not about outright changing you, but using culture norms to your advantage.

Think back to Rapha and dating in Denmark. She wasn’t changing her personality or interests to appeal to Danish men, just learning the rules.

If you want to get the rewards of those who play the game, you must be open to adapting.

How can you do that? I got an easy to remember formula for you.

***

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THE DRESSING S.M.A.R.T. FORMULA

(S)ee Things Through Their Eyes

Smart dressing should have a goal.

Whether thats signaling to a VC that you’re not corporate, or letting your Tinder date know you take care of yourself.

It’s important to look at your outfit and see it through their eyes. What message are you sending? What are their expectations?

This is where having a separate pair of eyes help. Ask a third party for brutal honesty, and take it. Don’t get upset or offended.

There are bigger things to focus on.

(M)atch Your Look To Fit Cultural Norms

A study at Princeton showed that people size you up within 1/10th of a second of meeting you, so it’s in your benefit to set the tone before from the beginning.

Dressing smart isn’t about completely changing your personal style, it’s about respecting cultural expectations and using it to your advantage.

Think of it of this way: The culture of Black Tie events call for a tuxedo, wearing anything other than a tuxedo is inappropriate and out of place.

If you want to be at the Black Tie event, it’s best to play the game of Black Ties, just as it’s best to avoid a full blown suit when meeting with VCs.

(A)dd Yourself Back In

Yes, match your look to fit into certain cultural norms, but you still have some room add some of you back into it.

Play with color, pattern and accessories. 

Just remember the cardinal rule: less is more.

Menswear doesn’t change as much as women, and part of being stylish as a man is adding small parts of your personality into it and making yourself memorable.

I like to think of it like putting a spin on a classic dish, like a burger. You still need a bun and meat for it to be considered a burger, but adding my own spice blend makes it my own.

(R)ules Still Apply: Fit, Color, Quality

Just because you should lean towards Zuck and not Bond doesn’t mean it’s an excuse to be sloppy.

The rules of great style still matter: Fit is the most important factor, color combinations should be pleasing, and quality never hurts.

(T)ry It On Ahead of Time

Breaking your usual dress codes can sometimes feel uncomfortable.

And nothing comes across as obvious as someone that isn’t comfortable in their clothes.

I have two golden rules about “new” when it comes to dressing for events:

1. Never get a new haircut less than 5 days before an event

2. Never wear a new outfit.

There will be times when you won’t have the luxury of breaking in your outfit a few times before a meeting. In this case, I recommend wearing the outfit the day before and morning of your meeting so you can get used to it. Just make sure you do check for stains and give it a good press with the iron.

***

3 ENTREPRENEUR AND VC APPROVED LOOKS TO GET YOU STARTED

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MARLED CASHMERE SWEATER: CLUB MONACO, $400 | BLUE COTTON SHIRT: DRAKES, $295 | BROKEN-IN CHINOS: J.CREW, $75 | BROWN BELT: SUIT SUPPLY, $59 | FILLMORE LEATHER BOOTS: PAUL SMITH, $675

UPSCALE STANDARD

“I always wear one of two uniforms: Khakis, collared shirt, brown shoes (with or without sweater), OR Dark jeans, white collared shirt, blue blazer. You can never lose with these outfits. Especially the first one. There are plenty of riskier outfits, some worn by the most successful of fundraiser. But if you’re looking for safe dress — these are it.” Jon Steinberg, Former President of Buzzfeed says.

Sure, Jon calls this safe. I prefer to call it classic. And just like a classic dish like steak frites, quality of the ingredients does wonders.

A white collared shirt is a little too safe for my taste here, luckily blues and browns work so well together. Drake’s beautiful deep shade of blue gives off a chambray feel, but pulls it back on the casual notch.

Top it with a cashmere sweater, much softer and less itchy than a wool, with just the right amount of warmth.

Matching the boots and belt in this case seems like you’re overthinking it when the brown is this light, opt for a darker shade for your belt and you’re good to go.

***

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ENGLISH TWEED BLAZER: J.CREW, $425 | CLASSIC BROADCLOTH DRESS SHIRT: BROOKLYN TAILORS, $175 | STRAIGHT-LEG SELVEDGE DENIM: RAG & BONE, $175 | SUEDE CHELSEA BOOTS: GRENSON, $440 | DARK BROWN BELT: SUIT SUPPLY, $49 | POCKET ROUND: ALEXANDER OLCH, $60

DRESSED UP DENIM

Turn the knob and lean towards dress up, without going full suit.

The blazer is a business classic, but ditch the tie and swap the dress pants for some dark denim.

Fit is especially important because you run the risk of looking like a middle aged dad trying too hard.

Make sure the tweed blazer fits your shoulders and your sleeves tailored to the perfect length.

Avoid flared or denim that’s too wide.

Suede chelsea boots show you got a bit more style over oxfords and are still appropriate, and the rich brown works beautifully with the blues.

***

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UNSTRUCTURED COTTON BLEND SUIT JACKET: BEAMS PLUS, $240 | COTTON-MESH POLO SHIRT: SUNSPEL, $165 | BREATHABLE BOXERS: EX-OFFICIO, $26 | PIMA-COTTON CHINOS: POLO RALPH LAUREN, $125 | BRAIDED LEATHER BELT: POLO RALPH LAUREN, $100 | LOW CUT SOCKS: UNIQLO, 3 FOR $9 | LEATHER SNEAKERS: COMMON PROJECTS, $410

HOT & HUMID

White leather sneakers for a VC meeting?

“Yessir. Perfect” TJ Parker says.

Business and warm weather can often be a brutal combination. My all time favorite secret weapon? Ex-Officio Give-n-Go boxers. Made of a diamond-weave mesh nylon/lycra spandex treated with Aegis Microbre Shield, these are the ultimate underwear for the heat (and year round for that matter). They stay  cool and are highly breathable.

The polo shirt has made a comeback recently thanks to Daniel Craig co-signing it in Casino Royale. (In fact, the Sunspel cotton-mesh polo is the exact one he was wearing.)

Minimal white sneakers balance out the casualness of this outfit without being too distracting, just make sure you add a barrier with low-cut socks to save your feet from blisters.

An unlined, unstructured blazer is the hot weather option for trying harder. But if its too hot, put it on right before you walk in and promptly take it off.

They’ll only need to see it on you for the first 1/10th of a second anyway.

***

YOUR TURN! HAVE YOU EVER USED STYLE TO YOUR ADVANTAGE? WHETHER IT’S FOR A JOB INTERVIEW OR A DATE, LEAVE A COMMENT BELOW. 

peter@theessentialman.com'
Author

Hi, I’m Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here