Dressing For Success... Stop looking like a fool.

[Kak]

It has come to my attention that few people give this enough thought.

A common theme of my posts is thinking big and leadership. Both of these REQUIRE interaction with other people. Sure you can build some onepreneur super outsourced company and make good money... But the VAST majority of the extremely wealthy got that way by making strategic deals, establishing influence and leading others.

Which brings me to LOOKING THE PART. It's popular, and often considered a badge of honor, in entrepreneurial circles to not own a suit, to almost intentionally dress like shit and not give a F*ck. To that, I ask, why? To what end?

I have learned how to dress properly when interacting with influential politicians and high-level C suite executives of very large companies. I have learned how to dress properly when I have to approach the lower offices with hourly workers. From formal meetings to business lunches, I have done it all. To say looking professional in every single interaction pertaining to your business is important would be an understatement.

Now, I'm no expert, but I am observant and have years of experience meeting people in person. There is no excuse not to look your best and present like someone who can back up the talk. It also doesn't have to be expensive.

Ask me anything.

 

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[Kak]

How do I look?

View attachment 19761

You'd look great if you were a mafioso undertaker from the Jersey Shore about to go to a ridiculous club after work... Not to a business meeting. Still better than the Zuckerberg hoodie.

The biggest problem is not enough contrast between the shirt and suit. The suit is solid black, which, outside of very formal circumstances, can make you look like the help, or an orthodox Jew wearing it for religious purposes. I can almost completely reccommend against buying black unless it is a tuxedo for a black tie event. Shirts need to be ironed. I have the cleaners use starch on the collars and cuffs.

A white shirt and a nice blue or red tie would clean this up and make it very business appropriate, but get yourself a gray or navy suit with very subtle patterning soon if you don't already have one. That would be very versatile.

Unbutton the bottom button and never button it again.

On a 2 button jacket. Unbutton the top button when you sit, rebuttoning it when you stand. Unbutton it when you walk outside on a hot day. Roll unbuttoned to make it a bit more casual if the situation calls for it. I would do it even more often because of the formality of the solid black suit.

 

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[SteveO]

Thanks @Kak . All you say is true and correct. Except... when you no longer need someone else's approval... thus Zuckerberg...

 

[Vigilante]

I love you brother but after I finish my current gig the only suit I will ever own again is from Billabong

 

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[MTF]

I understand this dressing advice, but a large part of why I am not climbing the corporate ladder and not owning a human resource based business is that I hate wearing suits and ties. I hate meeting new people as well, haha. That's just me.

Doing things that I do not like doing adds an unnecessary stress on me that I can better live without. I'd rather spend my energy doing something worthwhile than wear uncomfortable clothes to impress some people whose opinion I do not care about.

The way I see it is that @Kak plays the game on a different level. Do you need to dress for success if you're a solopreneur working on your e-commerce store? Not really as you don't interact with people face to face so there's no point in buying a nice suit if you aren't going to wear it anyway. If you're fine with running a small business, I don't think that Kak has a problem with that.

Should you pay more attention to your clothes when you negotiate with millionaires or billionaires who can potentially sign a 7-figure contract with you? I think so. It's a completely different world where every single detail matters.

 

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[Vigilante]

So I am at a shareholders meeting tomorrow on behalf of my company. I will be wearing a tie (sigh) but most of the shareholders will be less formal. I figure for the few times I actually plan to do this, I can play a role. To me it's like putting on a costume.

My mentor always dressed on step ABOVE everyone. That was his thing. He always wanted me to dress for success. I generally wore a polo or Tommy Bahama shirt and pants.

The one and ONLY time he ever saw me in a full suit and tie was at his funeral, as my final show of respect.

Kyle meets with senators, government officials, lobbyists, and CEO's. They still have a uniform.

I prefer to meet with my kid at the beach.

 

[Kak]

Thanks @Kak . All you say is true and correct. Except... when you no longer need someone else's approval... thus Zuckerberg...

I won't even pretend for a second that I know what its like to be Mark Zuckerberg. Those of you that know me absolutely know that I am not out to appease others, however, professionalism and dressing the part is absolutely in my best interest.

Hell, it is probably in Zuckerbergs best interest too, whether he cares or not. He can afford not to, but most on this forum, like myself, can't.

 

[Kak]

LOL i thought girls were mostly into this stuff since if a girl is dressed ugly no one will look at her. Now you’re all overthinking sh*t, if youre a man just have normal short hair, and dress as you want, exactly as you want , not how some smart a$$ on youtube will give you advice. And LOL at meeting with politicians, just another corrupt bunch that licks each other’s balls and just make money by shitting on people, and you have to impress them, really ? Anyone who is asking how to dress clearly wants to impress, but who cares about impressions

Not impress, or to attract attention... Just look the part.

So politicians are corrupt... So... They control a shit load of money.

People that want to actually make money can't go through life bitching about conformists, talking about the way things ”ought” to be, and expect to make anything of yourself. Like it or not, the world we live in is the way it is. If you show up to a business meeting with me and you look like you just rolled out of bed in the morning, the deal isn't happening.

Being the best, most professional version of yourself is in YOUR best interest.

 

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[Ninjakid]

Ask me anything.

How do I look?

 

[jon.a]

For me, it's the most uncomfortable attire, hands down.
Painful? No.
Aggravating, distracting and borderline claustrophobic? Yes.
I feel the same about just a buttoned up collared shirt.

Wow and I thought that this was uncomfortable...

 

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[Longinus]

Maybe just a regular office shirt would do fine? With short sleeves, as it may get hot in factory locations?

Don't.

Ever.

 

[Kak]

My go to with sport coats are almost 100% of the time a white french cuff dress shirt. 50/50 Jeans vs dress slacks. 50/50 light gray slacks, or dark gray slacks.

I don't really wear khaki, they remind me of my 2nd of 2 jobs I ever held. I was required to wear ugly khaki pants every day.

View: https://vimeo.com/277193592

 

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[Vigilante]

nope. It's 8 pages long lol. Just giving my opinion. I guess I spoke to soon? Oops.

I'm sure if you just throw on a pair of jeans and a t-shirt you'll be Mark Zuckerberg.

Sorry this thread is so long. We will try to keep threads to a page or two in the future to make sure you can actually read them in between video games.

 

[Kak]

Thanks, @Kak!

Now, many 9-5ers hate this apparatus....NECKTIES.

But I guess it's part of the attire.
What tie colours would you prefer? Why?
And do you have a standardized way of tying a tie? I used to wear one to school every day, I just tied my ties without strict measurements....so I got a random length of tie many times until I had some kind of gut feeling behind tying ties correctly lol.

And on shoes, I feel the definition between a formal shoes and non-formal is pretty blur, given that I have seen businesspeople wearing LOAFERS...felt weird to me.

@Kak, how would you pick your shoes? Is it the Kingsman saying: 'Oxfords, not Brogues'?

Shoes for a suit... Hands down Oxford lace ups. I prefer cap toe or wingtip with leather soles. I wear Allen Edmonds.

Wingtips can work well for more casual stuff too so if I was buying one pair they would be black wingtips.

Cap toe is more formal.

I would argue that there is a large difference between a dress shoe and shoes that would be worn with a tux which are generally a super high gloss patent leather.

Ties... Whatever, I buy conservative patterns. Not weird things. I am not a fan of skinny ties. I like red and blue the best. I usually use a half Windsor knot... Look it up. I have never found a need for anything else. A full Windsor can be a big bolder knot if you're feeling like it. You have to just practice to get the length right.

 

[Kak]

I love you brother but after I finish my current gig the only suit I will ever own again is from Billabong

Thats "dressing for retirement." LOL

www.tommybahama.com

 

[Vigilante]

Yeah, when I attend an event or dinner where I have to dress up, I do. My mom always taught me to dress exact to the occasion. Right now at my desk doing computer work, I'm naked, tonight we have to go to Dallas and I have to get dressed up and all fancy. I do hate when I think others are going to be dressed up and I get there and I'm one of the only people dressed up. There is a time and place for dressing every way, if only some people could match those times and places to the correct clothing.

Holy shit that was TMI

 

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[Kak]

I'd rather spend my energy doing something worthwhile than wear uncomfortable clothes to impress some people whose opinion I do not care about.

Once again... Not to impress, just to look the part. Impressing and standing out are not the goal. Exuding professionalism is. The more capable you come across, the better the deals you can swing.

You SHOULD ABSOLUTELY CARE about the opinions of the people you are trying to make a deal with. This notion of ”F*ck them” is ridiculous. Once again. It is in YOUR best interest. You're not doing this for them.

This is the last time I defend my position on why it's important. IT IS and those that don't agree are wrong. You cool cats that can't be bothered to look halfway decent because it's beneath you... Good luck... I hope you play the lotto because you can't make real money in a vacuum.

 

[Andy Black]

I had a video call with my largest customer today. Last time I did that I was wearing a t-shirt, but after reading all this I've put on a nice shirt this time.

I don't know if it's all in my head, but the energy was great and I killed it. Maybe there is something to it...

James Schramko talks about when he was selling high end AMG Mercedes. The wife of a prospect took him aside and told him to get a better tie. He went home a bit shaken but went out and got the best tie he could. He then felt a million dollars and his sales went up.

One of my neighbors cycled for Ireland at the Olympics. He told me he was thinking of creating a subscription box of fresh white socks for cyclists. Huh? Then he told me how some of the top guys pull on a pair of brand new socks before every training session and every race. It makes them feel a million dollars. So in their world a new pair of white socks is a performance enhancing aid.


Last week I was wandering around town running errands in shorts and trainers/sneakers/runners. I popped into a cafe to grab food and check in on work on my phone. I saw two previous clients talking to each other in the corner. I slipped into a booth before they saw me. If I’d even just been wearing smart jeans with my smart runners then I’d have cheerfully said hello and bid them good day.

Some of it’s in your own head, but what you believe affects how you feel and act.

When I was an IT consultant going onto client sites where everyone wore dress trousers and a shirt then I would indeed dress one level smarter. I’d not wear a tie, but I’d wear a suit jacket. I’d take it off after half an hour and muck in with the rest of the team.

I’m a consultant and I’ve even overheard managers talking to directors on the phone saying “Yes, he’s here. He’s wearing a suit.”

But I have to work with the techies so I can’t look like a salesman or project manager who doesn’t know his arse from his elbow. I also can’t make them look bad. Make everyone look good, especially whoever pays your invoices, and good things happen.


If the biggest PR agency in Dublin asks me in to help pitch to their potential new enterprise client then I’m not turning up in runners and shorts. That would be disrespectful to both the end client and my contact in the PR agency that’s put their neck out and vouched for me.

Will I wear a suit? I might... but without a tie. I want to look like someone who can do the work as well as talk a good talk. I might even dress in smart jeans and shoes with a nicely ironed polo shirt.

It’s down to who I’m meeting, why I’m meeting them, what I want them to think about me, and how I want to feel.

It’s also about showing respect to whoever you’re meeting. Often it’s the thought that counts. They can tell you’ve made an effort, and that’s a brownie point.

Wearing unironed or dirty clothes is just being a slob. I’m taking the kids to hurling training this morning. I’m wearing shorts, runners, and a t-shirt. As will everyone else. I’m sure some will be business owners etc. This isn’t an occasion to dress to impress, but I’m not turning up like I’ve just dived out of bed. (A bed that I made btw.)

I’m an adult. I’ll wear what I want to wear, and what I want to wear are clothes that show my respect for others, and for myself.

 

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[Vigilante]

I get what you're saying, but ultimately whether we like it or not, that's how the game is played. You can use it to your advantage (given how many people don't care about their appearance, you can easily stand out just by wearing a well-fitting jacket) or rebel against it and reduce your odds of success whenever it's important to look professional.

I get noticeably different reactions when I'm shopping in a nice jacket and tie vs wearing my sweaty workout clothes. Wearing a simple dress shirt in a restaurant will make most waiters treat you differently than if you're wearing a loose t-shirt.

If I want to communicate a specific message ("I mean business"), I wear a shirt and a tie. Do I feel super comfortable in it? Not really (though after wearing it regularly for a certain period of my life I got used to it). Does it get the job done? Absolutely - particularly if you're young and people can treat you like an inexperienced teenager if you're wearing a t-shirt.

Even if you're against the traditional approach, compare these two images (both show business consultant Bedros Keuilian):

Who radiates with power, business experience, and guaranteed results?

All things being equal, would you rather hire a business consultant in a v-neck and a baseball cap or in a suit? No matter what you think about wearing a suit, I'm pretty sure that you're more attracted toward the second guy.

I remember walking into a store one time ready to drop $10,000 in cash on what I was looking for. I was wearing ripped up jeans and a t-shirt. The salespeople literally looked right past me and pretended like I wasn't there. I can almost guarantee you had I walked in with a shirt and tie on they would have been hovering around me and getting me bottles of water while I browsed. If my memory serves this was in a consumer electronics Big Box store but you will see it most notably in car dealers and jewelry stores.

This is brilliantly captured in the movie Pretty Woman when Julia Roberts is shopping for dresses.

 

[GPM]

This thread needs to be bumped, because believe it or not, it is very powerful

Going in to a meeting as the best dressed person, and knowing your stuff. That is power. Being on the ball is all well and good, but when you look the part and look better than everyone else, that demands attention.

When you are swinging for the fences, you must look the part. No one wants to go into massive deals with someone who can't even dress themselves.

Psychologically I am on my game when I look good. I just feel better in my core, and guaranteed that comes across in how my interactions go. All this adds up for the potential for big wins.

And if anyone is wondering, yes I just walked out of one such meeting.

 

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[GPM]

I'm 27yo, single, south american, currently 9-5 corporate job and don't have any project, plan or business. Im starting from bottom with no money or big ideas.

@Kak is in the boardroom dealing with massive players while building multiple businesses which will be in the 8-10 figure range. Why exactly should we take the advice of someone with no money or ideas, rather than from someone with proven experience?

Fastlane you say? I am not sure how sitting on your computer and shitting on someone giving free advice on how to be successful is in any way even remotely fastlane. Perhaps it would be wise to do more listening and less talking.

 

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[amp0193]

Just read "The Magic of Thinking Big" (you'd like it @Kak if you haven't read it) and all of this clicked for me.

I get it now.

Gonna go back and re-read this thread and stop looking like a chump.

Went to a barbershop for the first time in my life yesterday and got a nice looking haircut. I feel more confident already.

New shoes are next on the list. Time to ditch the nikes.


I don't often need to appear to folks in "business" situations (yet). I just want to up my game in every day life clothing.

My wife thanks you @Kak.... "I've been trying to get you to do this for 10 years".

 

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[Kak]

I have a few suits and a few pairs of Allen Edmund shoes (the only dress shoes I buy... life time sole replacement and stiching! Well worth the price of the shoe)
@Kak My suits have a ticket pocket and functional cuffs (surgeons cuffs) are these details noticed in the higher end of the business world? Do you think it could be overkill or overlooked? Also, if I’m doing formal dinner, do I wear the shirt with cuff links? And can cuff links be “fun” in the higher end of things? I have these little F1 car cuff links and everyone seems to love them if they notice it.

I wear only french cuffs just because I like them. Those are nice details for suits, but unnecessary. To help the folks of the forum, I would say that there is ZERO reason other than your own enjoyment to go higher end than Brooks Brothers and Allen edmonds. It just needs to look good. 90 percent of people, even those that wear suits, won't be able to tell whether you're wearing a nice fitting Jos A Bank or a Brioni.

I would argue it is best NOT to try to be noticed for your clothing, but just exude professionalism. Leave no doubt in their minds. So with that said, the small details do add up and look nice but most people don't notice and that's a GOOD thing.

On one side of the spectrum, I have a Ravazzolo, on the other side I have Stafford sport coats from JC Penny that I LOVE. I have lots of Jos A Bank stuff and I also like Indochino.

I'll tell you the Ravazzolo is incredible, but I worry too much about it and almost never wear it. It has all the goodies like pick stitching, ticket pocket and functional cuffs.

 

[Vigilante]

It was sort of a pun. Here's the the thing you said the only time he saw you in a full suit and tie was at his funeral. How can he see you if he's dead?

You think I am going to entertain your morbid pun and attempt at humor regarding a discussion about my dead mentor?

I've only ignored one person in the history of this forum. I might have just made it two.

 

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[GPM]

@sparechange you can't even take the time to hit shift at the start of your sentences, or when using "I". I think that says a LOT about you.

I don't think you comprehend the scale of the deals we are going after. These are not some internet sales, or product sales. If the business will not scale to 8+ figures in a few years WE DON'T GO AFTER THEM. These are different people, and you interact accordingly with them. If you want to wear cheeto stained clothes then go ahead, this is not the thread that you need to bother yourself with.

 

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[CDNY]

No worries, @Kak! My apologies for disrupting your AMA thread. You took the time to do this and I should’ve been more open to your input. After thoroughly reading through this entire thread, I’ve already learned a bunch of different things I can do to dress better. Seriously, thank you so much!

 

[Kak]

The conclusion, if you hate fashion but good at making inventions you coop up with a sales guy

i didn't give crap bout fashion for a long time, but now i found a middle ground by dressing fitted.

fash·ion
/ˈfaSHən/
noun

1. 1.
   a popular trend, especially in styles of dress and ornament or manners of behavior.

Fashion is NOT what we are going for here. Fashion is what @The Abundant Man posted full of movie stars. Fashion people will buy skinny ties and tiny lapels and a suit so tight they'll look like a bobblehead.

Rico suave sales douche in his shark skin suit and his jet black greased back hair is NOT what we are going for here either.

I'm also not talking about wearing the same cheap, wrinkled, dress code, suit 16 days in a row like the 35k per year analyst on the 5:30 subway train living out his miserable existence.

Even the word "style" implies some sort of eccentricity.

We are ONLY looking at timeless business attire that has been the staple of American business for more than the last century. Clothes that make you look like someone that can do what you say you can do. The fact remains, we judge people on first impressions. If you look like a dipshit, you will more often than not be treated like one. If you look like an intelligent, capable and educated LEADER you will do better in business.

That said... this is why I like Brooks Brothers. There is nothing in the store I loathe. It's all classic American business.

@Vanderbilt this entire forum is devoted to entrepreneurship. A form of leadership. Ushering in the new. Leading people to adopt your visions of how whatever industry should work. We don't do that from the back room with our heads burried in some piece of technology dicking around with intracacies best left to the experts. There is a reason Ray Crock turned McDonalds into what it is today. There is a reason Waziniack needed Jobs. There is a difference between leader and expert. You can be both, but if your business is to outgrow your efforts, experts must be hired to their role.

 

[AgainstAllOdds]

Thanks for doing this. I have two questions.

1. Can you share pictures of what kind of suits/outfits you'd recommend everyone have in their closet? I'm planning to get some new ones made.
2. My business requires a lot of blue collar sales and I find it detrimental to over dress as it loses trust with the customer. Would you agree? Or how would you sell to blue collar small business owners?

 

[minivanman]

So what you are saying is that I should not wear my Galapagos Islands shirt that says I Love Boobs along with my flip flops? Did I mention I like to wear socks with my flip flops?

 

[Vigilante]

A friend told me a story that happened a few years ago in the town where he lived. There was a wealthy older guy in town who was a car aficionado. Another hobby of his was doing his own yard work, even though he could easily afford a landscaper.
One day, after working in his yard for several hours, he decided it was time for a new Porsche. He jumped in his truck and drove to the nearest Porsche dealership, still dressed in his dirty, sweaty shorts, t shirt and sneakers. He walked into the showroom and began looking at the cars, with his checkbook and ready to pay in full on the spot. The salesmen completely ignored him. After twenty minutes, he angrily left and drove to the next nearest Porsche dealership whose salesmen presumably didn't ignore him and bought a car. He then told this story to all of his wealthy friends which probably didn't help the first dealership's sales.
An opposite example is my girlfriend, who likes those expensive handbags. She has a nice collection, including a few models which she says are not made anymore and are highly sought after by collectors. I have been with her when she walked into designers stores (Chanel, Gucci, Dior) and seen salespeople descend on her like a swarm of hungry mosquitos offering her glasses of champagne. They spotted her bag and knew she had the money and willingness to buy.

My dad's old business partner went on to build a huge successful company. One day, he was out working on his dock at his estate in southern Florida. He lived on a peninsula, where on one side was the Atlantic and the other side was the inter coastal. He noticed his dock needed some staining (or something) so he was out working on the dock, when a tourist boat went by. The particular "key" he was on was an area where the boat operators sold famous home tours by water to star gazers. As the tourist boat floated by, he heard the tour guide say on the loudspeaker to it's passengers "and on the right you will see a worker. These estates have high maintenance and usually have a staff on hand like this guy to take care of the wears and tears of owning a beachfront mansion like this."

So many Fast Lane angles you could take on that short little story. Don't judge a book by it's cover.