Dress for Success

“Great men are seldom over-scrupulous in the arrangement of their attire.” – Charles Dickens

One thing should be clear: clothes do not make a man a gentleman or a woman a lady; and, by the same token, a real gentleman or a true lady is always a gentleman or a lady, no matter what he or she wears. The clothes you wear either magnify or cloak your personality and what you wear is in many ways less important than how you wear it.

I relaxed my company’s dress code today in hopes that there might be room for greater creative freedom, not just in apparel choices but in thought and deed. We’ve been heavily engaged in breaking down assumptions we’ve held that have prevented us in any way from making it easy for our clients to do business with us and this fashion statement was freshly pressed to that end.

The fashion choices we make are deeply personal. Like our food choices, they are based part on preference, part on need, part on availability and part on custom. Your clothing is a calling card to your personality, to your mood and to your outlook and your ability to dress appropriately can have a significant impact on how successful you are in any department of life.

It is possible to overdress. It is possible to underdress. At times it makes sense to overdress while it is less commonly advisable to underdress. The key is to dress in such a way that you do not hinder your effectiveness in life. Neutral or helpful is good. Hindrance is bad.

I’ve found that first impressions are important to people but at the same time I’ve always enjoyed the times when I’ve been surprised to learn that my initial impressions were incorrectly formed. Appearances can be deceiving and its worth remembering that fact lest you be caught in a web of prejudice.

In relaxing the dress code at my company I hope that everyone will rise to the occasion and take care to determine what is appropriate. We don’t live in a time like the Elizabethan era where what was worn when was formalized and rigid. That said, the art of appropriateness lives on.

There are those (often men) who say that they don’t really care about what they wear, but then when you look at them from one situation to the next they somehow end up not just fitting in but often matching what others around them wear. I was recently in a small town where every guy had a baseball cap on with sunglasses perched atop the cap. I was convinced of a fashion conspiracy, but were I to ask about it I’m sure that every one of them would have said that they put no thought to the ensemble.

There is no harm done in caring about what you wear, neither is there any problem in my book with not caring much about what you wear, unless your lack of concern gets in the way of you delivering the greatness that is yours to give. Clothing fitly chosen, like words fitly spoken are an aspect of your aesthetic and there is no reason to decrease the odds of someone receiving you due to a poorly composed aesthetic.

At the end of the day, it’s not so much what you wear but the goods you deliver that tell the tale. If you don’t have the resources to wear what you would like to wear, don’t be ashamed. Do the best you can with what you have and you can’t go wrong. As Albert Einstein said “If most of us are ashamed of shabby clothes and shoddy furniture, let us be more ashamed of shabby ideas and shoddy philosophies…It would be a sad situation if the wrapper were better than the meat wrapped inside it.”

258 thoughts on “Dress for Success

  1. Ndiluka Cristiano

    I really appreciated the tips. Very well structured and detailed. Albert Einstein was a very clever man by the way. This article was nothing more nothing less than impeccable.


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  4. Last night I was watching The Little people on TLC and the larger of the twin boys (can’t remember his name) was trying to help the smaller one improve his wardrobe and his skill set with the ladies. He said girls notice when a guy dresses nicely. I thought it was very bright of him and so sweet to try and help his brother like that.



  6. 網路創業

    Simply, one of the best article l have come across on this precious subject. I quite agree with your suppositions and will eagerly look forward to your forthcoming updates.


  7. Greg,
    Very impressive idea. I currently would be seen as overdressed for my current job. Although having the option to dress down is refreshing. I’m curious to see what results come from your change in dress code. Please keep us posted.


  8. Marie Chelle

    Thank you very much my friend, you are very kind in sharing this useful information with? others…. The details were such a blessing, thanks.


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  10. I thoroughly enjoyed reading this article. This is something I have thought about periodically throughout my life. I’ve gone through clothing “phases” where the time in my life dictated what was the appropriate dress for me.

    I’m glad to hear that you are willing to let people dress comfortably, yet approriate, for work. I believe this DOES help the individual to focus and be more creative at work. Especially, when they are not worried about trivial things like if their shirt or blouse is still tucked in nicely everytime they stand or sit.


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  13. I like to dress up and look good when I go to work but I absolutely agree with you. At the end of the day it’s the product that you deliver that’s most important, but looking good sure does make a difference.


  14. The first and last paragraphs really stuck in my head…. thank you! very interesting and intelligent blog. I am pretty classic and simple in my wardrobe, I am tall and thin/athletic and can’t wear a lot of the cutesy fashions for little women with hips. I like to show off my abs which no one makes clothing for! I love it when people show flesh. Not just tits or legs etc…. but something kind of sensual, maybe some back…
    I love having the freedom to wear what I want. 🙂 Summertime is the best, because you don’t wear a lot, so you can’t really go wrong in shorts or bikinis!


  15. A nice post, Greg. Measured, balanced and well tailored – just like a nice wardrobe.

    In my personal life, I would be completely happy to be, in Neil Diamond’s words, forever in blue jeans. However, when at the office or when giving presentations, the attire has to fit the occasion.

    A good rule of thumb for presenters is to dress as nicely, or slightly nicer than, your audience. And you can definitely overdress.

    When I was in Canada practising as a lawyer, I did a lot of environmental law. I often had to visit plants and factories of clients to speak to people about environmental due diligence systems and their importance. For the officers and directors, it was a full suit. However, when I had to go “down in the trenches” and speak to the people on the line, I would always switch to a pair of clean jeans and a nice buttondown shirt. Nicer than what they had to wear at work, but not so nice as to increase, rather than shrink, the distance between us.


    John Zimmer


    1. Thank you for your thoughtful comment this morning, John. I had a look at your website and loved the theme and your pointers. You’ll be featured in my next company memo. Thanks and keep up the good work!


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  17. Since joining the wordpress community, no post that I have read has given me the urge to write a response. I thank you for writing the first post that has done so.

    “but were I to ask about it I’m sure that every one of them would have said that they put no thought to the ensemble.”

    This is something I have thought about a lot. Being a guy, naturally, I have lots of male friends. Most of which, would never admit to putting much thought into what they wear on a day to day basis. My best guess is that they think that putting a lot of effort into the way you dress/look feminizes them somehow. I think that a large part of how men dress is directly related to how their fathers dressed. My father, being a pilot for the better part of my life, always had to be dressed sharp, no exceptions. I vividly remember him pulling out his shoe shining kit and spending at least an hour a week doing nothing but shining his shoes. Personally, now that I am older, I do not know a single man that does this anymore.

    While my father unknowingly taught me that no matter what, you always put your best foot forward, he knowingly taught me to act as a gentleman. A real gentleman. Dressing appropriately, and putting your best foot forward at all times, the two most important components of being a real gentelman.

    Now that I am 25, sometimes, while looking in the mirror as I dress myself for the day ahead, I can picture myself as a little kid, looking up at him wondering how he ever tied his ties.

    Thank you dad


    1. I take that as a huge compliment, thank you. My father and grandfather taught me the same lessons and I appreciate you taking the time to elaborate on the influences in your life. Have a great week!


  18. I believe it can go both ways. Sometimes it doesn’t matter what a person is wearing, its what the person has to offer, however, first impression does mean allot. Because if you do not have a good first impression, you just might not get the change for the other person to get to know the inner you. I say just play it safe and have a good first impressions so that people can get to know the real you and then you can relax on the outer impression.

    Great Post!


  19. tokyo24

    I agree with the sentiments you’ve expressed,but couldn’t help but feel if we all could remember that our appearance and attire isn’t the only thing to make us then we’d have a lot more self esteem.


  20. michvayn

    This was very well written. So many jobs create dress codes and it really keeps people from being who they want to be some times. But like you said its more important who the person actually is then what they wear.


    1. Thank you. Most rules or guidelines are there to minimize the repercussions of a lack of sensitivity. Rather than educate, most companies find it expedient to create rules that are enforced by other people who tend to hew to the letter of the law rather than the spirit of it. Such an approach is effective at preventing the worse from happening, but rarely does it draw forth something finer from those governed by it.


  21. Still, a decision what to wear shows who we are. Underneath we are all human beings, flesh and blood, which is beautiful on its own, but choosing how we want to appear to others and to our own reflection in the mirror is like painting a picture of our personalities.

    What you wear sets the tone of everything. I can wear practically nothing when I’m around my house in the morning and throughout the day, but if I need, for example, to make a super important call I feel like putting something on. Because I feel that if I talk on the phone naked I willn’t be as serious as if I wear a blouse.

    I absolutely love the Audrey Hepburn dress on the photograph! I also was wearing Givenchy for a very important lunch in London a few weeks ago, and the lunch went great!!!


  22. Hello Greg
    I came across your blog on wordpress and liked this particular entry. Although I think like you, society deems otherwise. Most of us, especially women, have to make every effort to “look presentable” no matter what, because first impression is really a lasting one, even if the personality or what is within us suggests otherwise once someone gets to know us.

    I know I have tried to look my best, appear my worst on bad days and in between looking casual, while being casual and yet on the days where I look my best (because I actually make an effort), I seem to get the respect I feel I rightfully deserve by those who don’t really know me well enough.

    So, although I appreciate casual days and the elimination of dress codes in a work place, I know if I am dressed for success on any given day, things appear different all around me.

    But thank you again for the wonderful article and I am glad I noticed your blog.

    Best Regards


  23. I have the belief that we are born with the “it doesn’t matter what I wear” feelings, and there comes a point when we discover that it in fact does matter to a certain degree. Depending on the person, this may have too early, too late, or just right. For me, I think I got it right. I understand that if I want to be taken seriously in the right situations, I need to dress the part. There are times when I can dress down, but you can always be comfortable. Well, perhaps except for at weddings…I personally don’t think many people are dressed comfortably for those. In any case, fantastic discussion. Congrats on being FP’ed!


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  25. Not having a dress code makes work so much easier. On the days I know I’ll be stuck behind the PC and work late, I wear jeans. Days when clients are in the office, I fancy myself up a bit. But not having to worry if it fits within the provide parameters just takes a weight off my shoulders. I could never work at a place where business attire was required. The pantyhose alone would kill me.


  26. what a great post, it’s makes me remember words that say “don’t judge a book based on it’s cover”.. and some parts of your post makes me remember of what people have done to me ’cause of what I’ve wear.. but I think it’s their opinion and I had my own too.. ^_^


  27. I enjoyed your post — the pic of Audrey Hepburn caught my eye – isn’t she gorgeous? Can you have a talk with MY boss? She dresses like she works on Wall Street and would love for all 20 of us to follow her lead, though no one visits our little upstate NY office and most of us sit at desks all day, interacting not at all with anyone but our co-workers.

    That being said, I think it’s true that I do act differently “out in the world” when I am wearing different clothing. I’m a hippie at heart but am often required to ‘go incognito,” donning suits and jewelry, hoping no one will find me out.

    And by the way, I think the caps & glasses WAS a conspiracy. You did well to walk on without asking. They were all obviously sworn to silence!

    Write on!


    1. Hepburn is, though I think many more people could be if they were not holding back. Outer beauty is much more a function of radiance than outfits and accessories, though I have no qualms about the latter if the former is in place!

      I enjoyed your blog, by the way! Have a great Sunday.


  28. “There is no harm done in caring about what you wear, neither is there any problem in my book with not caring much about what you wear, unless your lack of concern gets in the way of you delivering the greatness that is yours to give”

    Kudos for your exposition of true personal empowerment.

    One can continue to be a slave to others opinions for whatever reason or free oneself to practice our own brilliance in optimal wrapping.


  29. It’s funny I read this today, I have been trying on a new suit I bought and I feel like a skater boy trapped in a gentleman’s clothes.
    It’s not that I haven’t put on one before, it’s just that I don’t feel like it.

    Anyway, every time I think about dress codes and first impressions and the such I end up thinking people are stupid for judging someone by his clothes. And a second later I realise I do it all the time.

    Thanx for the post!


  30. Man, I’d love to have you as a boss. I went to uniformed Catholic school all of my life until college, so I can really appreciated the joys of going casual. Sweatpants are a godsend!


  31. I thoroughly enjoy reading the stuff on wordpress and after reading yours I am left wondering what is de rigeur…and I can only arrive at the conclusion that clothes does make the man/woman..and after that… speech and manners. Call me old fashioned if you will…..but I am particular about my attire and like every lady love new clothes. Any occasion is good enough to wear something new. I am also of the opinion that it cannot hurt to be polite and for this I look up to my husband of 29 years ….who is always so unfailingly polite and it is hard to keep up with him. I may slip up on occasions…but only at home and never never in public ……I hate scenes in public.
    Nice connecting ….have a good week.


  32. I think that’s great that you relaxed the dress code at work, it will most likely have a positive impact, because clothing is personal expression within the context of one’s environment, very tribal. The guys in the baseball caps and sunglasses are just wearing the “uniform,” they probably really don’t care what the uniform is, (be it khakis or a suit) as long as they fit in (or don’t stand apart from their peer group.)
    There’s really nothing wrong with dressing in “uniform,” and even creative types do this, what’s more important is what the environment they are dressing for is like, does it encourage personal expression in actions or ideas? empower? is it neutral? is it teamwork disguised as “follow the leader,”(I’ve had a job like that and I did not last long.)

    So as long as group thought is not stifled than neither will creativity or personal expression.


  33. A lot of what you wear in the workplace depends on what industry you work in. T-shirts in a banking industry or a suit in a construction industry would not fit in. Companies within the same industry often have different dress codes, too.

    When in doubt about what to wear in the workplace, I look around me to see what my boss is wearing and then try to dress similar to him or her. I also look to see what my peers and colleagues are wearing.



  34. I enjoyed this post quite a bit. I always make my initial impression of people, for good or ill, based not only on what they are wearing but how they present themselves. It isn’t about brand name labels and fancy clothing, but more in how the clothing they wear reflects their personality. It comes out no matter what–you can dress up the most ignorant, rude person and that’s still what they are underneath all the sparkle and spit-shine. Just sayin’.

    The end quote from Einstein was very aptly put–I had never heard it before but it’s great!! I also find it amusing because so many more people are concerned with their clothing and furniture but don’t give a second thought to the things they think or do, let alone what actually comes out of their mouth.

    This was a kick-ass post!


  35. jblack55

    As Albert Einstein said “If most of us are ashamed of shabby clothes and shoddy furniture, let us be more ashamed of shabby ideas and shoddy philosophies…It would be a sad situation if the wrapper were better than the meat wrapped inside it.”

    This is a great quote!
    That somes it up, you can’t judge a book by its cover. The clothes don’t make the man, the man makes the clothes. Good post!



  36. Very eloquently said, Gregg! I’m a student and I have most certainly noticed a change in my dressing from my first two years of medical school and now my last 2. When I started school at 22 years old I was pretty energetic, extroverted and looked at dressing as a form of art everyday. I would adorn myself with all sorts of colors, knick-knacks, and styles from different ages of fashion and different cultures all the time….. I just turned 25 and find that now I’m more introverted and not so much into flashy and trendy as I am into good quality, functional, and tasteful clothing. I’ve grown surprisingly conservative with my tastes. It’s quite fascinating! Perhaps age and stage in life strongly influence our personalities and this in turn is reflected in the way we dress ultimately. Hmm…. I wonder what I’ll be wearing 5 years from now…..


    1. Evidence of your sensitivity. Everything changes over time and inflexibility and the unwillingness to flow in relation to change are at the heart of the tension many people experience subconsciously. Thanks for your post!


  37. Style and substance are inextricably linked… I agree with your post. What you wear is important and how the person infuses the aesthetics with his or her way of carrying his or herself, the way the person talks… I personally like those that are unashamed and honest and bring their own personality to bear on the world, without falling to magazine or TV fashion trends…


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  41. Saw this a couple of days ago but did not have time to take a look. RE: If you don’t have the resources to wear what you would like to wear, don’t be ashamed. Do the best you can with what you have and you can’t go wrong. As Albert Einstein said “If most of us are ashamed of shabby clothes and shoddy furniture, let us be more ashamed of shabby ideas and shoddy philosophies…It would be a sad situation if the wrapper were better than the meat wrapped inside it.”

    Thanks for this! Geotravel


  42. you are a wonderful writer. my favorite is the first bit about clothes neither making a man a gentleman or a gentleman not a gentleman lest he chose ill-fitted apparel. i hope it goes well with you company and it’s according dress code.



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  44. Excellent blog! This blog was interesting and well written.

    I have always thought that choosing the right outfit for an event is very important. If you are not dressed appropriately, people will not take you serious, no matter how smart you are.

    That is a nice thing you did for your company. I am sure it will work out well as your employees have been used to a certain standard and will not stray too far away from that.

    Great quote at the end also. We should do the best we can with what we’ve got. As long as the effort is evident to look the part or to dress smart, one should be well received.


  45. The best thing is when you’re not judged for what you wear: everyone has a dressed-up and dressed-down style but that still differs from person to person. It’s important that everyone feels comfortable in their own attire, and this is the most important thing


  46. I respect people that “don’t care what others think” and choose to wear what they want…except when what they want is an eyesore and is downright distracting to others. Seriously, go to a small town Wal-mart sometime at 2 in the morning and check out what people are wearing. It’s downright ridiculous. I can do the whole t-shirt and jeans thing, but sometimes when it’s mini-skirt with a mesh top and some sort of horrible shoes that you have no idea where a human would even get them from, it’s time to start thinking, “Hey, is there a chance I could scare small children/be confused with a porn star”. If the answer is yes, for gods sake, change your clothing. I am all about free expression, but it goes a little far sometimes.


  47. I like people who is always dressed formally in public. Of course the whole image and behavior matters, but a good attire on a person ensures people around that it is worn out of the respect to the public. And nowadays it is possible to look tasteful with any budget. Thanks for the reminder


  48. I own a company where we work with business owners on refining their personal branding, presence and behavior to dictate all first impressions. Part of that process has to involve clothing and attire. I’m also on the board of directors for the charitable organization, Dress For Success San Diego. I found your perspective in this post to be very interesting and dynamic. Would love to compare notes somehow…


  49. “At the end of the day, it’s not so much what you wear but the goods you deliver that tell the tale.”

    I *like* that! Very well said, and a thought provoking blog all the way around. Everything you said seems so obvious, but it’s often the most obvious observations that need to be voiced in order to take root. (try sayin’ ‘obvious observations’ 10 times fast!)…

    I applaud the relaxed dress code for your company… coming from a company that’s really relaxed about it as well, I see the truth in your words every single day. If I wake up in the morning and jeans are the only thing that screams at me to wear’em, while it may not be the most appropriate office attire, it may also be the most relaxed, and the most creative/productive I am all week!


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  51. A very good article. Flips flops at work is something I will never understand! I don’t work but I see people wearing in various places that they really shouldn’t. And those slippy sliddy mules or whatever they call them that women wear everywhere nowadays are just glorified flip flops!

    The other day my daughter commented on the fact that at one funeral home (with lower prices) people dressed way too casual and cheerfully for a funeral and at the other one (higher prices) they dressed very nicely. I was very glad to see that observation from someone whom I would like to send to the TLC show What Not to Wear.


  52. Dressing well allows you to express yourself. It helps to get the attention of others in your office. It can also help in getting the promotion you’ve been waiting for.

    Do you know of websites that give guidance on how to dress for success?


  53. I am touched by the words of Albert Einstein: “If most of us are ashamed of shabby clothes and shoddy furniture, let us be more ashamed of shabby ideas and shoddy philosophies…It would be a sad situation if the wrapper were better than the meat wrapped inside it.”

    However people make judgement about us from our dressing first and then the rest.



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  56. Very well said.

    I think schools should post your article outside their office, for the enlightenment of both teachers and students.
    The sight of non-PE teachers wearing T-shirts and sweaty yoga pants to class hardly inspire respect and confidence
    from students. Not to mention the midriff-baring tops or lingerie worn on the outside by alot of young women.

    Though I it is important to know that “It’s what inside that counts”, what we wear and how we conduct ourselves in public/private is of equal importance too!


  57. To quote Einstein is fabulous! and I do think the clothes do make the person. You have so much choice in all price points to pick from and should remember that people do make snap decisions based on appearance, you really should try to make the best impression possible at the right opportunity. Comfort can be saved for home, that’s when I strip off the under clothes and put on the soft cloth, but I always dress to the nines when leaving my house, it’s just the way I AM!! I like to put my best foot forward and like to look my BEST!! It is a pleasure for me, there can still be a happy medium for others, and I believe that all people should try to look, neat , clean and a step above the way they do currently. I do NOT think sweats are GOING OUT to EAT ATTIRE!!

    Just one of my gripes, or Rants!!


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  59. I will bookmark your blog and hope that you will give us an update in a year on how much this move has improved quality/productivity/creativity in your work place.

    Based on my experience it will have the opposite effect!


  60. Love it and Love the Einstein quote! I often admire the fashionable clothes of some of my girlfriends, but I realize that it doesn’t change who they are. That’s what you’ve gotta remember. Great message.


  61. Nice perspective and hope your employees will truly embrace your relaxed dress code (not all employers are as flexible). I agree with what you say in that wearing what is appropriate is key. Although our company has a “business casual attire” dress code, our department is the “exception.” We are allowed since we are normally not in contact with our clients. Based on my own opinion of appropriateness, I stick to Fridays as the only days that I wear jeans. Thanks for the nice post and congrats on Freshly Pressed! LB


  62. Félicitations Gregg! Je suis entièrement d’accord avec vous.

    I wish you were my boss so I could wear what I want to the office. I will start working for the first time next month after graduating from a business school, and I’m anxious I’ll feel disguised wearing a suit instead of my usual Converse and jeans. I’ve worn these during my internships in luxury companies and it wasn’t a problem because I always tried to dress in a simple yet fashionable way and did my best at work. If only it could be the same everywhere!


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  64. Like they say, the person should wear the clothes and not the other way around. I find that individuals who have low self-esteem often hide in the clothes that they wear, either very lavishly or the exact opposite.

    I wish though, that we could all wear anything we want without people taking judgement on our preference, style or class. That is quite impossible though, we are just but humans! hahaha

    Great post! 😉

    I love Audrey Hepburn!


  65. Nice posting. I am always fascinated by how men like to wear uniforms – if there is no uniform, they create one. While women, in general, like to dress in unique manner. A black tie event is for me the perfect example – if a man wears the wrong type of tuxedo he is in trouble. If there are two women with the same dress one will hide in bathroom and cry!


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  67. I appreciated that a lot. I do own a lot of different types of clothes but just because I want to throw on gym pants and a t-shirt doesn’t mean that I’m not going to “bring it”. Nicely done!


  68. sayitinasong

    True- and it is the person CARRYING the dress that makes the outfit…good case in point- I went to see the exhibition of Princess Diana’s clothes at kensington palace- and the dresses there were plain(ish) and some quite garish (well, it was the 80s after all…) but in the pictures where she is wearing them- they were absolutely fabulous!!


  69. Hey!

    Great post! First of all, I love that you said the words “Freshly Pressed” in the post, and got Freshly Pressed. Coincidence?

    My office is sort of going through dress code confusion. Some staff feel that we should be dressing more professionally, but some feel that we should be able to dress more creatively. We are an event planning company, and are more creative that the average office… for example an accounting office. I am on the side of the people that think we should be more creative. If we dress like ourselves, and are free to express who we are in ways such as clothing, then we will feel more creative and produce an even better product.

    When we are young, we are told by our peers to dress like everyone else so we fit in and are “cool.” As I got older, I realized that actually the more we dress in clothing we love and the more we stand out, we are more likely to be perceived as our new definition of “cool.”

    Keep up the great blogging!
    ❤ Milieu


  70. it is a nice post.However, i think that our appearnce (clothes) is impotant for us and to others , for us because it makes more happy & for others because it send amassage about ourselives & emotions.


  71. Interesting. From my perspective, as a owner of a wardrobe and image consulting firm, I find the ‘dressing down of America’ somewhat sad.

    I think it is a reflection of our society, our values and our overall approach to day to day task. We like things fast, easy and comfortable.

    Like anything else there are pro’s and con’s to this; but the nostalgic part of me longs for the day’s of three piece suits, pocket watches, the idea of a woman’s ankle being erotic, and yes even a corseted bust.

    But, practically speaking I am sure your employee’s will appreciate the dress code change.




  72. apparentemente


    looks like an in-between line, dressing properly is important, but should not be devoted too much importance to. Dressing is par of your “visual impact”, but a good commercial might as well lead to a poor product. To say give your dressing appearance the right weight.


  73. I typically do not have the resources to wear what I would like to wear. Chalk it up to having 2 children. Tis very true that it would be sad that a wrapper be better than the contents inside. What is even sadder is that I witness this all too often.

    A wonderful read. Thank you. Einstein… Genius even by our standards today.


  74. Ishana

    Very well-said. My problem is that clothes rarely fit me the way they are supposed to (apparently small females with hourglass figures are a rarity, go figure). Which means I have to take extra care in making sure I look nice for work, without anything showing that I don’t want to show.

    Our clothes are part of the pictures we paint of ourselves. While our personalities are the focal point, our attire should be a suitable accent, whether matching or contrasting.

    Thanks for the post, Gregg, you’ve given me some things to ponder.


    1. You’re welcome! Thanks for your comment. I like how you described our clothes as a part of the picture we paint for ourselves. Rather than see clothes as producing new self-worth it makes much more sense to see them as magnifying the self-worth that is already there!


  75. Ha, as a former academic I’ve had a lifetime’s worth of the “people shouldn’t care what you look like”. They do, and in my experience people most people aren’t as happy as you to find their out their initial assumptions are wrong.

    Still, good for you for trying, and for quoting Einstein, and congrats on being Pressed!


      1. ecoquisitive

        I think it does. Our survival depended on those instincts and observations (or so it seems). You had to sum up the situation without giving yourself time to think, or you might end up on the wrong side of a pointy object.

        I wonder if we’ll ever get over those old compulsions, or if we need them now more than ever? We fill our world with so many external trappings, online and off, it can be hard to delve into the real person sitting inside them all.

        As for me, I like comfort over fashion, so if I can find something that looks and feels good to me all at once, that’s a good day! We have a business casual office, yet there’s a whole range of styles going on depending on the department, position, who you’re trying to ape–er, emulate… 🙂

        One of the things I’ve noticed in my office (and in high school and middle school; not so much in college) is the tendency for a lot of women to greet you and then immediately drop their eyes to your shoes. Idle curiosity? Instant judgment call? It always seemed a bit odd, especially when you’re still responding to their greeting. Brain’s up here, folks. But then I never agreed with the “shoes make the outfit” schtick. The person makes the outfit.

        Per Anna’s comment upthread, I’m assuming that’s not a blanket statement that all folks wearing darker colors have low self-esteem. By contrast, one could say that people wearing loud, splashy colors have low self-esteem that craves the attention they’ll draw. I don’t think we can truly apply the If p, then q logic here.

        In any event, Gregg, this is the first post I’ve encountered of yours and I will definitely be back for more. You’ve given me a lot to think about.


      2. Perhaps..although, ironically, academics really seem to pride themselves in dressing poorly, as though this “proves” their intelligence. Just as ridiculous as the opposite, all things considered.


  76. Always great to see another blog about clothes. It’s one of my frequently-revisted topics too, though focusing more on the psychology of clothes than fashion.

    Re: “There are those (often men) who say that they don’t really care about what they wear, but then when you look at them from one situation to the next they somehow end up not just fitting in but often matching what others around them wear.”

    This reminds me of that wonderful speech Miranda has in Devil Wears Prada of how no-one is immune from fashion and trends, even if they think they’re being subversive or anti-fashion. In fact, the more you think yourself free of trends, the more likely you are to be unconsciously trapped by them, rather than being able to express individuality by rising above them.

    Congratulations on being Freshly Pressed!


      1. Yup, on that I can definitely agree: insight is key to defining a personal style.

        Without insight, the risk is of either becoming a fashion victim (by buying into every single latest trend), or blindly following the herd into uniform anonymity.


  77. This is fabulous.

    I also think that what people wear reflects their self-esteem. Those with low self-esteem tend to wear darker and more understated clothes as they don’t want to draw attention to themselves. And those with a higher level of self esteem are less afraid to wear brighter colours, or push fashion boundaries.

    Sometimes this doesn’t work. Sometimes people wear clothing to shock others and cause comment – because of their low-self esteem and confidence. They may not be comfortable with attention but want to be noticed to add validation in some way.




    1. Interesting observations, Anna. I wonder if children could be taught to use their clothing choices as a means of magnifying what self-worth they have. To do so they would first have to identify what self-worth they possess at any given time…another useful exercise! Despite the many calls to “fake it until you make it,” I am a firm believer that you can’t give what you don’t have.


    2. @Anna

      Wearing brighter clothes and pushing the boundaries of fashion to garner attention are a pretty good indicator of low self esteem. On the other hand I wear black tee shirts and black jeans because I work in a factory and sometimes stop off at a store on the way home. I used to wear white tee shirts to work but didn’t care for how dirty they looked by the end of the day.

      @ Gregg

      A few years ago George Will called men who wear jeans and shorts little boys because that’s what in his opinion little boys wear. I have always considered that statement as elitist bigotry spouted by those who wear nicer clothes let prefer to hire someone else to do the dirty jobs needed doing.


  78. I agree with what you are saying but the other side of the coin is what the expectation is of a business customer paying good money from a company or team of people for professional services. The margin for “creativity” is not exactly a sizable one when you are expected to dress in a way that represents your firm. Obviously, those who have more concern or interest in the clothing they wear everyday are more apt to find ways to individualize that still align with corporate protocol. The possibilities are there if you’ve a taste for it…. but don’t show up to my company wearing flip-flops because you are being “creative”.


    1. My expectation is that creativity needn’t compromise the reputation of professionalism and care that we’ve developed over the last decade-and-a-half. The key to that happening lies in the development, and continued refinement of sensitivity on the part of every team member to know what is right, when. Thanks for your comment!

      P.S. Haven’t seen any flip-flops yet, but there is neither sand nor sea kelp in the office so I’m trusting that they are unlikely to appear any time soon.


      1. Very well said Greg. I was walking through my university campus yesterday and saw a girl wearing a potatoe sack over her head while performing the most beautiful ballet I had ever seen. The people who seem to think that the way you dress at work is important are the same people that accept the excuse “I was just doing my job.” I want to thank you for exposing the intelligence in creativity and putting an end to institutionalized thinking in your company. You, like Dickens, are a great man!


  79. DeeDee

    Audrey Hepburn has always been a symbol to me of beauty, graciousness and generosity, no matter what she was wearing. I love the picture of her you included with your post!


  80. Colin

    I once knew someone that, whenever their poor clothing choices were remarked upon, proclaimed loudly: “I don’t care what people think”! I always thought this was foolish. If your beliefs go against the prevailing norms, and you feel they are worth fighting for, by all means, fight for them and be different. The world needs more people who are willing to stand up for what they believe. I did find it hard to understand how jean shorts and a stained t-shirt were a worthy cause, especially when the situation caused for a nicer attire. I always think it should be a “pick your battles” type of deal. However, I think an argument could be made for dressing nicer than then the current casual in everyday life. I guess just chalk it up to a fundamental difference of opinion! Thanks!


  81. Isabelle Kearney

    Well said. I appreciate the concern you have to bring out the best in those that work for your company. To create an atmosphere of creativity and self-expression is so important, while expecting the highest and finest of each one. Appropriateness definitely comes from the inside – to have a sense of what to do, say or wear should be dictated by each individual situation. Kudos!


    1. Stephanie

      I think this is so true! I like how you said “its not so much what you wear but the goods you deliver”. Sometimes people get so wrapped up in what someone is or isn’t wearing they forget that the person may be a hard worker. On the other hand first impressions can make or break you. Hopefully with you relaxing the dress code for your company it will allow for more creative freedom from your employees.


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