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

Kak

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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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kelvinfernandezm

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I enjoy Eastern spirituality for its simplicity and non duality. In those philosophies you are taught to look at everything the same. A homeless man, a rich man, a stone or a nugget of gold you're to look it at with the same eyes. Even though I do my best to follow those principles, I know other people do not.

The majority of people judge you by what you wear. Specially in today's western society where people wear the things which they identify with. In my case I'm sort of stuck in my teenage years style wise. I have no clue where to even begin to change my dressing style. I dress like I just came out of 2006's rap music video (without the baggy pants). On top of that I'm a minimalist, if you went in my closet you are only going to find some white t's and jeans and one pair of shoes.

Honestly I'm starting not to like that, for the simple fact that I know people are judging me for what I wear. I don't mind buying more items to add to my closet to get a new look even if it means breaking the rules of minimalism. Can you please help me get a new style. I want something simple, something that I can wear everyday but still looks business like.
 

Kak

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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.
 

Kak

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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.
 

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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'?:playful:
 

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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?
 

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

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Kak

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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?
Yes, will do.

Is this blue collar sales role your primary need?

Weird question, but what part of the country are you in?

Jeans and a sport coat work great in Texas and probably most of The South for anything from blue collar/meetings with the working class, up to lunch meetings at all, but formal venues.
 

Kak

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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'?:playful:
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.
 

ZF Lee

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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.
Ohhhh now I know what to call them!!! (after a googling session on wingtip images) Where I come from, everyone just calls them 'smart shoes' lol....

I must have surrounded myself with some folks who are less aware of the nicer things in business.

I think I have what you call cap toes. Don't think it is Allen Edmonds though. I don't think the brand is in my country anyways, unless it s a minority brand here.

Now on belts, @Kak, what would you recommend? Anything more special than the ordinary?

And on socks, somehow I have spotted folks wearing short white socks with the shoes, and it doesn't feel good to me intuitively. What do you typically wear? The longer dress socks?
 

Kak

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Now on belts, @Kak, what would you recommend? Anything more special than the ordinary?

And on socks, somehow I have spotted folks wearing short white socks with the shoes, and it doesn't feel good to me intuitively. What do you typically wear? The longer dress socks?
Belt- The ultimate would be to buy one that matches the styling of the shoes. Otherwise just match the color.

Socks- You can't go wrong by matching the slacks. Yes long dress socks. No wild patterns, subtle conservative patterning if any.
 

Cruze

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Really interesting thread - and thats right. The first impressive to your business partner is very important. You perceive someone in a different way who is well dressed than when he comes around the corner wearing T-shirts and flip-flops.
 
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ZF Lee

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Really interesting thread - and thats right. The first impressive to your business partner is very important. You perceive someone in a different way who is well dressed than when he comes around the corner wearing T-shirts and flip-flops.
Same goes for university.

I have never been so disgusted seeing male peers coming in dressed in lazy slippers, dressed rather weakly in sleepy t-shirts, and looking as if they came to take a nap than attend a class (and yes, they do take naps in class!). Turns out that the free-loaders in group projects also DRESS shabbily. So, that can be a red flag to look out for.

My horror applies the same for girls. Wearing shorts that are too short, with flip-flops that scream 'immaturity' to classes.

Folks who dress like that don't tell me that they are game for the task at hand.

And on hairstyles, please don't dye your hair too harshly! A slightly different hue of brown is fine, but a screaming orange or a sharp dash of pink? What does it tell people? I feel that this is a pet peeve for me.
 

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Don't.

Ever.
Why not?

I haven't found the need for construction site visits yet, but I read newspapers with business folks attending to project openings in somewhat that entire, with safety helmets.
 

Kak

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Olimac21

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For those interested in dressing better, I find two youtube channels: Based Zeus (dating+fashion advice, cheap clothes and tips on mindset too) and Teachingmenfashions (a lot of grooming advice and clothes).

That being said, my recommendation would be to go minimalist with clothes because is very easy to overspend if you listen to all people´s advice on what you should were.

If you do not like minimalist or owning just a few clothes, try sharing clothes with people who have a similar size than you, buy second hand or just keep a budget limit to it.
 

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Yes, will do.

Is this blue collar sales role your primary need?

Weird question, but what part of the country are you in?

Jeans and a sport coat work great in Texas and probably most of The South for anything from blue collar/meetings with the working class, up to lunch meetings at all, but formal venues.
Thanks. Midwest. Chicago.
 

Supercar

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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.
 

DustinH

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For those interested in dressing better, I find two youtube channels: Based Zeus (dating+fashion advice, cheap clothes and tips on mindset too) and Teachingmenfashions (a lot of grooming advice and clothes).
I watch Real Men, Real Style, the Gentlemen's Gazette, and Sartorial Talks. I will check out the TeachingMenFashions.

These were helpful in learning about little things such as how to wear a pocket square and new ways to tie a necktie.
 

garyfritz

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I have probably 60-70 ties -- and I haven't worn one in years. My current function has me interacting with customers frequently, but as a tech expert, not as a sales guy. I started out with a jacket and tie, and rapidly realized I was dressed about 3 levels higher than 98% of my clients. Now I wear slacks and a nice shirt and I still out-dress the clients.

I really don't care for the current fitting style for jackets and suits -- fitted so snug that it looks like you're busting out of them. Fabric puckered and straining a bit against the buttons when you're in a relaxed neutral position, and worse if you actually move. It's like the "skinny jeans" of jackets, but it seems to be the style for young men. I'm 61 and I don't care for it. I'll stick with jackets that have enough fabric to reach the buttons, and pants with enough inseam to reach my shoes.

Suit.jpg
 

MTF

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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.
 

minivanman

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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.
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.
 

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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.
 

Vigilante

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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
 

ChrisR

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Crazy timing with this thread. I recently got a new sales job that I'll be starting soon so I've really been needing to figure all of this out. I've mostly been watching youtube videos on this matter and they have helped a lot. I've already found some gems in here that I wasn't able to find elsewhere.

Thanks Kak!
 

DustinH

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I read a book a while back about how to be a "Rainmaker" in your organization (I am in real estate so this is an important concept for me personally). The book had somewhere around one hundred things rainmakers do that other people do not. The only concept that really resonated with me enough for me to remember it to this day said "the rainmaker should dress to be the best-dressed person they will see that day."

That makes total sense to me. Does that mean wear a suit and tie everywhere everyday? No. It means dress a little better than anyone else in the crowd in which you surround yourself. Just always be a little bit better dressed than everyone in the room.
 

dompie85

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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.
 

Kak

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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.
 
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Kak

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I read a book a while back about how to be a "Rainmaker" in your organization (I am in real estate so this is an important concept for me personally). The book had somewhere around one hundred things rainmakers do that other people do not. The only concept that really resonated with me enough for me to remember it to this day said "the rainmaker should dress to be the best-dressed person they will see that day."

That makes total sense to me. Does that mean wear a suit and tie everywhere everyday? No. It means dress a little better than anyone else in the crowd in which you surround yourself. Just always be a little bit better dressed than everyone in the room.
Not bad. I can get behind this .
 

Kak

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I really don't care for the current fitting style for jackets and suits -- fitted so snug that it looks like you're busting out of them. Fabric puckered and straining a bit against the buttons when you're in a relaxed neutral position, and worse if you actually move. It's like the "skinny jeans" of jackets, but it seems to be the style for young men. I'm 61 and I don't care for it. I'll stick with jackets that have enough fabric to reach the buttons, and pants with enough inseam to reach my shoes.
TOTALLY 100 percent agree. They still sell the classic business suit. The party douche suits as I like to call them have no place in the boardroom.

And by douche suits I mean:
Anything shiny
Anything super bright and colorful
Anything so slim you look like a bobblehead
Anything with tiny lapels
Anything with giant lapels
Skinny ties
Shiny shirts
Funky patterned shirts
I probably missed some this is just off the top of my head.
 

Philip Marlowe

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Great thread, @Kak

I couldn't agree more on appropriate attire. I setup an appointment to meet with a guy for some design work. When I got to his office, he was wearing an old hooded sweatshirt, smelled like cigarettes, and hadn't shaved in days. Nice guy, but I knew right then it wasn't going to work out. Maybe that's wrong, but so be it.

Not to hijack, and just my two cents, but you really just need a few quality items. Allen Edmond's can last a decade when polished and re-soled, as can Florsheim or Bostonian. Go to Jos A Bank for a nice two-button suit when they're on sale and TAILOR the suit coat, not just the trousers - don't let them give you the jacket fit off the rack. Get 2-3 decent ties with crisp, white shirts (please avoid the TJ Maxx package deals with the gray/orange/red shirts and matching tie). Add a classic, used watch (Omega is always safe) and you're good for every wedding and graduation.

If you want to go up a few levels, make the shoes Edward Green; the suit Brooks Brothers (1818 is fine); French-cuff shirts as Kak says; and the watch a Breitling or Rolex.

-PM
 

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