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How Should Entrepreneurs Dress?

secretentourage

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I recently had a chat with a younger Entrepreneur on his way to a business meeting who asked me "Do I have to wear a suit?" I asked him what he was planning on wearing and he said jeans and Tshirt cause its really who I am. It made me wonder how others perceive how Entrepreneurs who are not given a dress code should actually dress. Here are my thoughts on it. Please provide your perspective and opinions.

Perception is reality and seems to still be the case in 2013. As further established Gen Y gets, the further we seem to get from proper attire and more towards rugged daily wear. This begs the question as to if dressing well to appeal to the masses is still important, but also who are the masses worth appealing to.


With age comes experience and regardless of our understanding of subject matters, it isn’t until we have lived through something and applied our knowledge that we complete a full learning cycle. Dressing for success is no different as our definition of what success looks like and what we believe we should look like, is also subjective to our experience level.
From my perspective and based on my experience level, entrepreneurship is about freedom and the ability to change the status quo but is also about being a role model and carries a significant level of social responsibility along with it. Therefore dressing well on your journey may hold just as much importance as dressing well for your victory party. Remember that during your journey it is very likely that you will need a network, friends and mentors; all individuals who will help you shape who you are to become but also lend you a hand or point you in the right direction when needed.


How do these people find you and how do they relate to you enough to join? First appearances still matter and what held true 10 years ago, still holds true today when it comes to how we make friends. We make friends based on our ability to relate and common interest, and our appearance is often the first way we attract or push back new individuals we meet. Anything from the media to simple business relationships will accept or reject us based on the message our attire shares about our values and beliefs.


Regardless of how well you dress in your own perspective, it will always attract individuals who share similar values and belief and therefore may limit your success if your choices are too much to the right or the left. Instead try slightly altering the image of success so you find the perfect balance of dressing well while retaining the freedom behind being an entrepreneur. Think about that freedom as your ability to tweak today’s standards rather than rewrite the code of how society functions. Instead of changing the new standard of how people should dress at work and throwing away your suit, try to simply not wear a tie. As much as you may understand the symbolism behind wearing jeans and a T-shirt to work, others who do not share that same belief and sentiment outnumber you and unfortunately will not relate to you thus separating themselves from you rather than joining your cause and supporting your beliefs.


It is important to understand that your entrepreneurship journey starts the moment you choose to create, innovate, and re-design the way people do business or think, but is isn’t until you succeed that you are given the title of entrepreneur and have the opportunity to change how society acts and what its accepts.
 
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Tom.V

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I work at home all day, every day. I conduct all of my business over the phone or email. I wear a t-shirt and gym shorts ALMOST every day of the week with a comfy pair of Saucony's. Because I can.

As for social standards and the opinions of the masses, they don't matter. The tiger never loses sleep over the opinion of sheep.

</Vig Rant>
 

NVaz

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I think it depends on the occasion (event) but i would suggest to whenever it is possible to dress in a way that makes you feel confident, that's the most important imo.
 

smarty

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what about Steve Jobs style? :)
sjobs_610x407.jpg
 
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Thriftypreneur

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This is definitely one of those "It depends" topics, in my opinion.

If you're a billionaire entrepreneur with multiple large successes under your belt and a reputation to match, people won't really give a shit about what you wear. Ok, maybe some will, but at the end of the day, they may not approve of your dress code, but they'll still be buying whatever you're selling.

If you're an up-and-comer, still trying to network, still trying to build your reputation, and all that stuff. I would say how you dress is probably one of the most important things you should think about on a day-to-day basis. I don't care what anyone says, people ALWAYS judge books by their cover and first impressions set an overwhelming tone for how others will perceive and react to you. Dressing like a slob will only make things that much harder because you instantly start out working your way uphill.

It takes work to look good. People know this. I think dressing like a bum basically tells people "I'm lazy and/or I don't care enough about myself to bother."

Obviously for those who work at home the majority of the time, it's really a non-issue. Although, personally, I find I'm way, way less productive if I wear PJs all day. So, while I don't wear a suit to sit a home, I do get dressed every day. To each their own, of course.
 

Allen

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I agree that if you are already a successful, financially independent entrepreneur, you can pretty much wear what you want, when you want. If you are successful and show up at a fund raiser wearing jeans and sandals, you will be considering brilliant, creative and quirky. However, if you have not yet made your mark in the world and show up at the same fund raiser wearing jeans and sandals, you will simply look like any other lazy slacker.

If your business process and business systems have you working on the computer or phone all day where no one sees you, by all means wear what is comfortable. However, I am still a strong believer in first impressions and a stylish and well tailored suit, with or without a tie, will never, ever, hurt your reputation! Plus, in a world of jeans and t-shirts, it makes you stand out, especially at events that cater to the successful.
 

AllenCrawley

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I work at home all day, every day. I conduct all of my business over the phone or email. I wear a t-shirt and gym shorts ALMOST every day of the week with a comfy pair of Saucony's. Because I can.

Fair enough but if you had a meeting with potential investors or potential clients would you show up in a t-shirt and gym shorts?


As for social standards and the opinions of the masses, they don't matter.

Ok, forget the masses but the opinions of those that can directly affect your business do matter.
 
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theag

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I love dressing well and wearing suits. Can't afford nice stuff right now though and also don't have much face-to-face customers contact right now due to my online marketing job, so for now I mostly stick to jeans, dress shirt and (sporty) leather shoes. Also not worth investing in new clothes right now because I intend to lose some more weight / gain more muscle first.

But in the future I see myself walking into million dollar meetings in an expensive custom suit, rather than sitting on a beach running my business from a laptop. ;) Everybody has different priorities/goals. I guess thats why I'm kinda trying to find an "offline" need/market that I can serve, instead of building a (passive) online business, like most people here.
 

Allen

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I love dressing well and wearing suits. Can't afford nice stuff right now though and also don't have much face-to-face customers contact right now due to my online marketing job, so for now I mostly stick to jeans, dress shirt and (sporty) leather shoes. Also not worth investing in new clothes right now because I intend to lose some more weight / gain more muscle first.

But in the future I see myself walking into million dollar meetings in an expensive custom suit, rather than sitting on a beach running my business from a laptop. ;) Everybody has different priorities/goals. I guess thats why I'm kinda trying to find an "offline" need/market that I can serve, instead of building a (passive) online business, like most people here.

I've been wearing suits most of my adult life while working as a soldier in corporate America. Thoughout those years, I've learned that a $300 suit that is well-tailored looks a lot better than a $800 suit that is not well-tailored. Point being, it doesn't cost that much to look good! Find a style/brand that fits your physique and lifestyle and make it your own!
 

Tom.V

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Fair enough but if you had a meeting with potential investors or potential clients would you show up in a t-shirt and gym shorts?
Maybe just for shits and giggles, but I'd probably throw on something nice for such an occasion as first impressions are obviously important. All other times non-business related, I could care less.
 
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Kak

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The "its who I am" people are full of crap. Does anyone honestly think a suit and tie is natural apparel for an everyday routine? Of course not, unless you are forced to. It is however a matter of professionalism and respect in doing business.

A t shirt and jeans for a business meeting, because its who you are???... Give me a break. Who you are is going to get you thrown out of my office.

Now.. Only an idiot would put a suit on to sit in front of a computer all day.
 

splok

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he said jeans and Tshirt cause its really who I am. It made me wonder how others perceive how Entrepreneurs who are not given a dress code should actually dress. Here are my thoughts on it. Please provide your perspective and opinions.

My perspective is that I'd be instantly skeptical of anyone whose identity is defined by (and limited to) a certain style of dress.

My personal opinion is that clothes are a tool and that they contribute to our accomplishing (or not accomplishing) our goals to varying degrees, so we should wear whatever clothes optimize our chances of success. If you're pulling a long day of work at home and feel more productive when you're comfortable, then by all means, code in your undies! If you're trying to convince someone to invest, you should carefully consider your own attractiveness and their proclivities before showing up in your underwear...


Now.. Only an idiot would put a suit on to sit in front of a computer all day.

Well, to be fair, what we wear can affect our behavior and performance:

Science!
"A recently published study from professors at the Kellogg School of Management at Northwestern University shows that when research subjects wore a scientist’s or medical doctor’s white coat, they performed better on a test"
 

Aututto

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I actually have read through most of a book called "Dress For Success" and it really helped me understand this issue.

If you are totally self employed and spend most of your day in front of your computer at work; then you can wear whatever makes you happiest.

Now meeting with investors, clients, customers, and sometimes partners; you should do your best to look professional. You can rave and blab about all your success but you are no greater than the mass of society.

You think Steve JObs attire is a good example? Well if you know anything about him he was hot headed and full of his own success. Required his employees to be professional while he wore jeans to work. The result? He got fired from his own company. So I would not go down that route.

When do you see people like Trump or Gates wearing gym shorts a t shirts? Never because that attire is kept for private. Gates almost always has on a nice shirt at the least.

To sum it all up; no you don't have to dress well to succeed. But it certainly does affect the people you attract, show the people you work with that you care, and help increase your chances of succeeding more.

This whole "wear what you want" bandwagon bs has so many flaws that get looked over. Just use some common sense when you dress yourself for the work your doing. Like it or not; people judge books by their cover. Just remember that. You could rise to richest man state in a t shirt in shorts but it won't be easy. Work smarter not harder.

Successful people use everything they can to help boost their success.
 
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Aututto

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My perspective is that I'd be instantly skeptical of anyone whose identity is defined by (and limited to) a certain style of dress.

My personal opinion is that clothes are a tool and that they contribute to our accomplishing (or not accomplishing) our goals to varying degrees, so we should wear whatever clothes optimize our chances of success. If you're pulling a long day of work at home and feel more productive when you're comfortable, then by all means, code in your undies! If you're trying to convince someone to invest, you should carefully consider your own attractiveness and their proclivities before showing up in your underwear...




Well, to be fair, what we wear can affect our behavior and performance:

Science!

Just realized you said essentially what I said. Oops! Well thats two supportives on success dress :)
 

Mike Kavanagh

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I wear what I want ... Because I can.

Though you should try different things. If you just get set in one way you don't get to experience other things. Dress well.
 

MJ DeMarco

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Dress for the occasion and for each situation.

Dress to eliminate friction.

If you walk into a Fortune 100 company with an objective to sell them 10,000 units of your new invention, do you think showing up in jeans and a t-shirt is acceptable? How about a meeting with a couple of VC's who may or may not invest $5M in your business? Any attire outside of normal would cause friction and potential objections to your sales goal. Do you really want someone to say "Ya know, I really like his inventory management system, but who shows up to a meeting in flip-flops and a Hawaiian T-Shirt? Can rely on this guy for software support if he's sitting on a beach all day?"

Any appearance friction can become a sales obstacle and that is a detriment to your goal. (The exception obviously if your dress is related to the product -- if you're selling Margarita Mixes to a Bev Distributor you could probably get away with the flip-flops and beach shirt.)
 
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Get Right

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I dress according to the client that is buying my service(s).

One day it is a suit, one day it is jeans. Sometimes I change 2 or 3 times a day. Make THEM comfortable talking to you.
 

dknise

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I've been laughed at for wearing jeans, t-shirt, and Nike's plenty of times at startup events. Every, single, time it comes up I will go into a discussion comparing actions. Maybe the person across from me accusing me of my clothes is dressed better, but every single time I am winning in the actions race. They are always looking for a partner or an idea.
 
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FastNAwesome

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In my experience dressing sharp + acting accordingly is HUGE when dealing with gatekeepers, lazy administration workers who do only what they have to (and try to estimate who they can screw around with and who they cannot), and also to be taken more seriously in banks and business establishments in general.

Also as already mentioned, it's a matter of respect to people you do business with. Btw. I know we're not a "get-a-job" crowd, but at times when I needed a job, dressing properly helped me a lot, as I basically almost always stood out as the ONLY one who actually wears a suit. I also have friend who is an employer and he says people have become so careless and disrespectful, they send CV's with silly photos, illiterate etc. This basically means - just be DECENT and your chances of an interview go through the roof.

I guess my point is wear a suit when appropriate, but also know how to carry yourself. Be a gentleman and a class act, only then it's full effect. I love that expression...it would be a huge compliment for me if I ever overheard that someone says "that guy is a class act".
 

theag

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I've been laughed at for wearing jeans, t-shirt, and Nike's plenty of times at startup events. Every, single, time it comes up I will go into a discussion comparing actions. Maybe the person across from me accusing me of my clothes is dressed better, but every single time I am winning in the actions race. They are always looking for a partner or an idea.

Thats most likely true. But now imagine you show up dressed sharp AND with all the actions under your belt. Your outcome can only improve by doing this and its almost no extra effort as it doesnt have to be expensive clothes.
 

AmyQ

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Our office is casual, not business casual. We all probably look unemployed to outsiders

We all own at least 3 business casual and business wear outfits as well. You never know when opportunity is going to knock, and sometimes you have to wear a suit to answer the door.

As far as wearing a t-shirt because "that's who I am." I am not my clothes. My clothes are a tool that I use to protect me from the sun and germs and, occasionally, to present an image that will further my goals.
 
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