This is a fantastic primer on how to fit clothes. Since taking care to get well-fitted, nice clothes, my confidence has skyrocketed and I seem to get more respect. This is a great way for career advancement - ever notice managers are generally better-dressed (ignoring Zuckerberg, the exception to this rule)?
What I recommend to get started is go to a consignment/thrift store such as Goodwill and liberally buying cheap clothes that fit decently well. For shirts this mainly just means ensuring the shoulder crease lines up with the "angle" at the end of your shoulder. Take them all to an alterations store and have the nice lady fit everything for you. This will be the most expensive part of this whole endeavor. As a result you'll get a better feel for the types of clothes that work best for you as well as how clothes are supposed to fit, all for relatively little upfront investment.
Also get nice shoes. Reddit's malefashionadvice is notorious for advocating Clarks Desert Boots. There's a reason for this; they're fantastic. I own a pair, wear them all the time. Whatever you do, don't wear sneakers around unless you're a personal trainer. You're probably not in high school anymore, and nice shoes will instantly help you present yourself more professionally.
I would like to provide a counter-point. Disclaimer: I am a girl...
I hate wearing "fitted" clothes and shoes...god how I hate shoes...I have spent the last several years of my professional career wearing flip flops or sandals around the office.
I have never worn pants suit, in the winter I opt for a hoodie, tshirt and jeans - and generally substitute the jeans for a skirt in the summer.
As a result, I am biased towards people who wear suits (especially with ties!) - The question in the back of my mind is "what are they trying to hide?". (It should be noted that these observations are from corporate land where I no longer reside.)
I have met people who believed that simply because they were in a suit they should be listened to...even when it was clear they had no knowledge about the situation at hand - this tends to apply to project managers and the like.
When I met somebody in t-shirt and jeans I tended to get along with them, they tended to be knowledgeable and could stand their ground.
I have since moved out of corporate land, and into an environment where tshirt and jeans is the norm - and these people "get shit done" - their career development and self esteem comes from the fact that they are the best at what they do...not because "I look good this morning"
You shouldn't get respect from the clothes you wear...you should demand respect from the skills you have.
You make some good points, and I probably should have made mentioned in my original post about how I too prefer wearing comfortable clothes when appropriate (I don't sit around my house in a suit like Barney Stinson). For example, I'm currently lounging around my kitchen in a t shirt and gym shorts. But when I need to be around people, especially at work, school, and social events, I personally feel more confident when my clothes fit better, are free from holes, and I'm wearing my nice shoes.
Also, for example, the other day I organized a "Restore the Fourth" rally for my home town. As the organizer, I felt it necessary to look nice and presentable because people generally respect nicer-dressed people, and I knew I would be interviewed for the evening news. If I had worn sneakers, gym shorts, an ironic t shirt, and a neck beard, things would not have run nearly as smoothly as they did.
Have you ever intentionally dressed like a slob? I think it's a great way to build confidence because most of the interactions you'll have with people will start with them assuming negative things about you. When you see them realize that those negative assumptions were unfounded it I think it can help you un-link confidence and clothing.
"Have you ever intentionally dressed like a slob? "
Or as I call it "dressing like a Physics professor". You'll notice that people who need to work with their minds very rarely dress well, and people who use other attributes dress very well...often inversely correlated with how well they can use their minds as a tool.
An article like this shooting to the top of HN is a consequence of the rise in status of programmers. Probably nothing can be done about it, but an article on how to conform is the antithesis of hacker culture.
That's something different. By "conforming" I meant "conforming to the mainstream", which is the type of conforming the OP (and the root comment) is about.
(Edit: I agree that subcultures have their own conformity rules.)
Shared cultural values in the US definitely do not include well-fitted clothes, outside of niche markets like fashion or design, in major cities like New York.
Please don't meta-moderate my contributions to this community.
Really, why is that? I don't believe I said anything controversial. I personally haven't met anybody who, given the choice, prefers looking like a disheveled slob.
For one, people who wear sneakers often do it because they are comfortable. To equate them to high school teenagers if they are not personal trainers is quite unfair. You are free to advocate a more professional look, but if you get disrespectful on the way, people are going to hate your stance for it.
I stand by that statement more-so than any of the other ones, and I'm sorry if you found it offensive. Sneakers have no place in a professional environment. There are plenty of comfortable options for professional footwear.
Why would sneakers have nothing to do in a professional environment?
Unless type X of footwear professionally disables you in some sort of way, I think the statement "[X] have no place in a professional environment" is rubbish.
In a professional environment where you're trying to sell/ negotiate, I agree with you. It's a natural reaction to make assumptions about people based on how they dress, and anyway in which you can give yourself an advantage is valuable.
Any other professional environment I disagree. Why?
I wear crocs to work. I wish I could go barefoot. What does footwear have to do with software development?
So, here's the deal with tech companies, lax dress codes, and professionalism.
When business came about, there was a general idea that the quality of a person and their business dealings was reflected in the way they presented themselves. This was a big deal back when you had to physically interact with the businessperson. If their appearance was sloppy, cheap, unclean, or otherwise with no care put into it, often the products would reflect the same lack of care.
Fast forward to present-day. Joe Emacs sits in his Herman Miller, his "No, I Will Not Fix Your Computer" t-shirt stained by cheetos and free mountain dew. His sandals expose his grimy, untrimmed, twisted toenails. He smells of BO, either because he forgot to put on deodorant or hasn't showered in days, probably due to "marathon coding sessions". His hair is also greasy and smells.
Joe Emacs likes to shout over his cube to his co-workers, because why should he make the effort to get up? Joe Emacs likes to leave trash all over his cube. Joe Emacs blares youtube clips over speakers instead of headphones, annoying all his co-workers, preventing them from working. Joe Emacs likes to talk loudly about subjects that bother or annoy his co-workers. Joe Emacs is an asshole.
Compare Joe Emacs to Fred Altair. He comes to work in crisply ironed chinos and a dress-shirt or polo. His hair is combed. He smells nice. His brown leather shoes gleam in the fluorescent light. His desk is neat and tidy. He walks over to his co-workers and politely asks questions without interrupting. He uses headphones, and doesn't discuss religion, politics, or other controversial topics in the workplace.
It doesn't matter which you would prefer to be. Joe Emacs is going to annoy his co-workers and make it a shitty place to work. Fred Altair will be appreciated by his co-workers, and make it a much more relaxing place to work.
But it's not about clothes. It's about professional attitude and environment, which is to say, respecting your co-workers and not becoming a burden on others. If you can do that while still wearing Crocs, by all means go ahead.
I don't understand. How does clothing choice have anything to do with respecting your co-workers? I think being judgmental about someone's sense of style is more disrespectful to your co-workers than wearing fitting, popular clothing.
The clothing choices I mentioned are more classic examples of behavioral stereotypes.... I don't encourage being judgmental at all. It's really not what you wear, but how you wear it and how you comport yourself in the workplace. But there are limits.
Barefoot is just not acceptable. it's unhygenic. Nobody wants to smell your feet, and even if your feet aren't smelly, you're at risk of developing a fungal infection, injury, etc. Wear some shoes.
The other aspect to picking a particular style or dress (let's call it "conservative dress") is that it makes people more comfortable. People are weird. Often they get uncomfortable if people around them dress different than they're used to. You see it in tech workers all the time: they say "I'll never wear a tie! Oppression!" or somesuch thing. Ties make them uncomfortable, just like people in shorts, sandals and a t-shirt with a slogan might make other people uncomfortable. Something in the middle would make everyone more comfortable, which makes for a better work environment.
But the way you dress can influence the way you and your co-workers behave. In my experience, dressing more relaxed leads to more relaxed personalities, which has both great and horrible side-effects. People think they can act however they would with their friends, which (for tech types) might be very abrasive to strangers. It may also affect their work, or how they compose themselves in meetings. I can't tell you how often i've heard the causally-dressed guy tell someone to fuck off in a meeting, while the guy in business-casual is much more tactful. These are just some examples.
I have very little "work" experience, but from my limited experience I've noticed the opposite effect, the guy in a suit is way more likely to be a bully. That being said, I can imagine people acting how you say. I think that a company that has employees that act this way is seriously dysfunctional and I have no desire to contribute to that.
"I have very little "work" experience, but from my limited experience I've noticed the opposite effect, the guy in a suit is way more likely to be a bully."
After about 20 years in professional work, I can confirm that the nicer the suit, the bigger the asshole. The hack is to dress in a nice suit as well and then don't back down when the bully bombasts all over you. You'll probably end up with a promotion. Not backing down form a T-shirt position will probably get you laid off.
Just want to say, I love this post. It really shows the idea that presenting yourself professionally is much more than just looking nice. It's about respect for yourself and for others. When I read some of the comments in this thread and picture the writer, I imagine Joe Emacs (brilliant phrase btw) with his worship of anti-conformity and contrarian attitude. Not someone I enjoy working with. Certainly there are exceptions, but in my years of working in tech, especially the startup scene, I've definitely seen this trend and want no part of it.
And I guarantee you people take you less seriously as a result of it. You can say "their loss!" and scoff at the absurdity of it, but that's a coping, rather than fixing, mechanism.
> Sneakers have no place in a professional environment.
Tell that to Billy G, Stevie J, and just about every programmer that works for IBM, Microsoft, Apple, Intel, and Google. I'm guessing you don't really know that many programmers that work at mainly tech companies.
Even if you work in an environment which borders on unprofessional, dressing this way has many benefits. People will regularly comment on how good you look. They'll take you more seriously. You'll gain a little more confidence and pride in properly accomplishing a given style. And you can use it for the rest of your life, until the point at which your centuries-old duds go out of style (which probably won't be in our lifetime). Other people in your workplace may notice this and make an effort to clean themselves up a bit, too, which may affect their interpersonal skills and work ethic. No guarantees, but it can't hurt.
Oh, and ladies go crazy over well-fitting clothes, especially suits.
Yes, yes, yes. Many tech companies don't have the kind of environment professionals like to work in, because they foster an environment so casual it borders on 4th of july drunken barbeque.
Why would it have that environment? Usually mismanagement, but also the culture that becomes ingrained from the company's inception. The problem is when the culture is so slanted towards certain behaviors that they go a little too far and become problematic.
There are plenty of comfortable options for professional footwear.
Please let me know. I've tried for almost 20 years to find a pair of decent work shoes half as comfortable as a pair of knock off $10 sneakers. I try to get by with choosing decent looking sneakers, but it's a lost battle. Mens dress shoes are made for a foot shape that mine obviously isn't.
The most comfortable shoes I've ever worn are Keens, followed closely by Vans, then Merrels.
My local shoe guy has tried in vain for years to find me a pair of nice work shoes. His last best effort was Mephisto, which are awesome shoes and an awesome company, and completely unwearable for me after a few minutes.
I personally haven't met anybody who, given the choice, prefers looking like a disheveled slob.
I prefer wearing gym shorts to slacks. If that preference qualifies as "wanting to look like a disheveled slob," then a large fraction of the population wants to look like a disheveled slob.
More generally, I prefer not to worry about things like brands of clothing.
It's fine that others do. I'd agree you didn't say anything controversial or offensive. But, fashion isn't for everyone.
>I prefer wearing gym shorts to slacks. If that preference qualifies as "wanting to look like a disheveled slob," then a large fraction of the population wants to look like a disheveled slob.
I don't think there's any argument about that.
Any man, over 20-22, that wears "gym shorts" casually looks like a disheveled slob.
Well fitting clothes are comfortable too. You don't need to get brand name items either. There's nothing wrong with not caring about fashion - indeed, people shouldn't be judging others negatively just because of fashion. However, why not also look good? It can benefit the social aspect of your life a lot, by giving you some added confidence. So if you're looking to improve that part of your life, dressing well is a good place to start.
> I personally haven't met anybody who, given the choice, prefers looking like a disheveled slob.
Not calling people names, whether or not it's due to their clothing choices, is going to earn you more respect than the clothes you personally like to wear.
> Because a t-shirt with cola and burger residue is what characterises a hacker and an independent spirit, right?
Preferring a t-shirt doesn't mean you don't care about food stains on your clothes.
I wear high quality t-shirts, jeans and sneakers that look, fit and feel great (to me). They aren't fancy, but niceness seems pretty subjective. My wardrobe is nice to me, maybe not to anyone else.
Personally I gauge the niceness of my desk and car by their utility and enjoyability, same with my clothes. There are certain utilitarian requirements for each, it's pretty much about personal opinion after that.
If you are in a profession that requires a "uniform" then I may have some empathy for your ideas. Otherwise, I am mentally unable to grasp the need for this thinly-veiled, vapid, conformist outlook regarding external appearances.
Anti-conformity to the "mainstream" seems to be a compulsion, or even an addiction, with self-described hackers. Why not maintain the hacker ideals of innovation and disruption while hacking others' perceptions of you to make yourself seem more trustworthy and respectable? You will surely wind up with someone of the sort as your boss. That's just the way the world works.
Anti-conformity to the "mainstream" seems to be a compulsion, or even an addiction, with self-described hackers.
You are correct. Is there a point though?
Why not maintain the hacker ideals of innovation and disruption while hacking others' perceptions of you to make yourself seem more trustworthy and respectable?
Precisely. And this cuts both ways. Hope you can see that.
You will surely wind up with someone of the sort as your boss. That's just the way the world works.
Sure, hence HN, YC and the audience here that is actively striving towards being their own boss. Actively changing the way the world works as part of their striving for freedom from such bosses!
There's nothing there that says you have to wear a suit and tie to work. It's a guide for wearing clothes so you don't look like a bowl of oatmeal. Rules are always made to be broken once you understand how the system works. Male fashion doesn't mean you have to wear slacks and button down shirts. I wear jeans, sneakers and tshirts every day. But I've learned how to buy clothes that look like they fit me and less like a cholo gangster.
Your choice of dress depends on both your age and the environment you're in. I definitely wouldn't wear trainers (sneakers) to work, but equally I also wouldn't wear anything other than trainers to certain clubs. It's very easy to look over-dressed and pretentious if you're 18. Equally it's very easy to look like an idiot trying to wear teenager's fashion if you're 30 and cruising about in high tops.
I absolutely agree that fit is crucial for clothes. However, everyone has a different context and you really don't want to look woefully out of place. Sometimes that means wearing (nice) trainers.
> managers are generally better-dressed (ignoring Zuckerberg, the exception to this rule)?
Managers dress better because they have a softer skill set that depends more on perception than hard results. Zuckerberg is a hacker, with a hacker's mindset. That's why he doesn't dress up.
To be fair, plimsolls such as Keds make for fine casual wear and can often be integrated into nice outfits, so long as you take care with regards to the sizing and coloration.
Somehow I associate suits with either dishonest people who use them to try and project false integrity (salesmen, bankers, recruiters, etc.) or servants who are forced to wear them by their masters[1] (porters, security staff, heck in some city offices even the cleaners wore them).
Since I like neither dishonesty nor subservience and find ties incredibly uncomfortable, I intentionally don't wear any such thing. It is astonishing how much we read into clothes though. I was regularly mistaken for a bouncer while standing outside a club wearing plain black clothes (despite drink in my hand).
"Somehow I associate suits with either dishonest people who use them to try and project false integrity (salesmen, bankers, recruiters, etc.) or servants who are forced to wear them by their masters[1] (porters, security staff, heck in some city offices even the cleaners wore them)."
You associate it correctly in all cases. As somebody who's come to appreciate suits as a powerful tool, it's worth learning the game. Wear a suit to a car buying negotiation and save a few thousand dollars on your next car, or wear the "livery" of your company and find yourself promoted faster than if you don't. It's stupid, but most people are stupid.
(I've learned how to wear a suit without a tie, try and project a comfortable, casual, glamorous [bm]illionaire look, they almost never wear ties with their suits [1][2][3]
I associate suits with making me feel like a million bucks -- at least when they fit well. And i firmly believe nothing looks worse than an ill fitting suit.
Also, black at night is fine but most people should avoid black during the day. It compliments very few complexions.
Suit advice:
I'm 30. Most the people I work with and talk to about clothing are in my age range, say, 25-35. Not "young" still, but we don't feel old and certainly don't want to put on a suit and see our fathers in the mirror.
If you relate to that, and want something more contemporary, I'd suggest taking a look at Theory. They are on sale right now 50% off and are a value at that price. I don't love them as much for the full price. They are sold as separates and you can pick one up now for $375 or so.
These jackets are partially canvassed (not bad, not great), have spandex or lycra in the blend that gives them a TINY bit of stretch, and the single vent and width of the lapels is modern enough to look good on a young man, and classic enough to still look OK in 5 years.
I think this is a balance. Well fitting clothes (suits or not) do enhance a person's appearance and speaks to their attention to detail in that area --they may or may not apply to other areas. On the other hand, dressing without dedicating much thought can come from, among other things, being too busy with 'important' things, the person is kind of lazy, at least in terms of dress, or perhaps they think they're being anti-pattern --but they're not, as many other people do the same.
That said, most people who wear suits, to address that area, don't really wear well fitting (bespoke) suits. Ill fitting suits are worse than down dressing or dressing like a slob --it says you're being rote and don't really pay attention to detail. I see this symptomatically in salespeople, and others you mention, yes indeed, it looks horrible.
A well fitting suit and matching clothes do enhance people's aesthetic look and that bleeds into their professional appearance, rightly or wrongly, in my opinion.
By the way, if your stay-at-home clothes fit well and they match in color, pattern and mood, they don't have to be special or expensive. They need to match you in some way, however. It can't be a mishmash of incoherence. It becomes a visual cacophony and can be hard to get past.
It's like looking at the person preparing your food and seeing them sweaty, clearing their throats, wheezing and uncomfortable, yet, they're washing their hands and at no point sneezed or coughed and never touched their face before finishing the preparation, but it still seems gross.
Nobody's body is an amorphous blob, male or female.
It's simply a matter of design and convention - clothes are designed to fit some body types, and conventional clothing styles are predicated on "degrees of freedom" of possible design that can only comfortably suit some body types without looking like a tent or a gorilla suit.
Actually "male" formal styles have more give in their degrees of freedom than informal styles for either gender, or formal styles for women, because fat men have often been suit wearers.
Still, IMO, designers ought to see "fat people of any sex" as a challenge to their ingenuity. I'd really like to see what people would come up with if effort was applied, rather than merely shifting the proportions of something designed for thin people.
Mid-high end brands build their clothes to an aspirational fit model. Most people are forced to make that fit work for them, either through tailoring, or optimizing around what attributes of their clothing are important to them. Fashion is pretty backwards on fit - bottom line is wear your clothes the way you want to wear them, swag or no swag.
I feel your pain, but I don't see how the recommendations would change for blobby men. The only issue for blobby men following these recommendations is that it's really hard to achieve the desired results with off-the-shelf clothing.
For example: IMO, most big-bellied men shouldn't be tucking-in a dress shirt unless they're required to. A better-looking alternative would be to buy a dress shirt that's one size larger than what's needed and wear it untucked.
The problem I have with dress shirts - as someone who "shouldn't" tuck them in - is that by virtue of being dress shirts, they are longer because they are designed to be tucked in. Casual shirts are generally OK.
Plus, going a size larger doesn't hide my belly as much as I think it does.
As noted by another poster: I'm better off working on the belly than finding the right length shirts and debating tucked in vs out!
I'm not thin and never will be. Even when I worked out 6 days a week for 2-3 hours a day, had a resting pulse of 46 and a body fat percentage under 10% I was still built like a square.
Ignore this claptrap. Find good rules that fit your body within the following guidelines:
1 - shoulder fit is important, nothing says you don't know how to dress yourself like bad shoulder fit. This works for T-shirts to tuxedos
2 - sleeve length is important
3 - find comfortable pants you look decent in, don't hide anything, just fit in them well. What you wear up top is far more important than what you wear on the bottom
"Before we jump in, let us note that clothes best flatter a fit body. "
I'd say the statement in the article is more accurate. Fit rather than thin. And if you are not fit I'm thinking it would be better to work on that before the fashion.
Everytime I see an overweight person who's wearing nice clothes that fit well, I don't see an overweight person. That is, the well-fitting clothes take away from their being overweight almost completely, at least in my perspective. You do make a good point, however, that those folks would probably want to untuck their shirts.
While I study biochemistry in school, I will not pretend to be able to give medical advice, so I can't answer your question with regards to medication. However, for those overweight folks who just haven't been tending to their diet and exercise as much as they'd like, leangains and a good strength-training program is a fantastic way to shed fat and become more "fit." Although, if you're really interested in getting involved, I personally believe http://rippedbody.jp to be a better resource for the information on leangains (although leangains.com is the original source), simply because it's better organized and more straightforward.
The amount of weight one gains due to medical problems seems to be overestimated. I mean, there are medications out there that will hammer your metabolism. But then again, your average guy with Hypothyroidism, high blood pressure and below average testosterone levels won't take such medications.
A friend of mine has Hypothyroidism and he attributes gaining nearly 100 lbs to that because his doctor told him that might be the effect of it beeing not treated for so long.
I find that pretty silly. It may add some water weight and another 10 lbs due to that and skew the balance between lean body mass and fat. But the body has to follow the laws of physics and adding 100 lbs of mass in fat requires massive amounts of calories above your daily expenditure for extended periods of time.
"No pants should need a belt to stay on your hips."
So I suppose I should quit pants altogether, or only wear pants with elastics, since I can't find pants long enough for my legs that don't fall off anywhere. I have only one pair that fits me without a belt, and I had to buy it in Spain (I'm from Argentina); apparently teenagers are taller there so a they had my size.
I know these articles can't work for everyone, but it really bothers me how hard it is to find clothes for some body types.
>So I suppose I should quit pants altogether, or only wear pants with elastics, since I can't find pants long enough for my legs that don't fall off anywhere.
Or, you know, you could always have the longer ones adjusted at a tailer.
Or you could order made-to-measure pants if you are such an outlier.
I know there are solutions to the problem. I don't particularly care for going to a tailor, so I wear belts (which are also hard to get in my size, but using kid's belts is viable, and I change belts a lot less than I change pants). But I'm still annoyed whenever I have to shop for clothes; it's an extra effort I don't care for.
This would have been pretty useful to me back when I was 15-18. I've got some heinous pictures of me wearing a suit jacket that was much too large and dress pants that were far too baggy. And pleated.
God, they had me until they made the mistake of advising against pleats. I personally prefer them, but I'm not going to say which you should wear, and anyone who does is trying to trick you.
Pleats come in and out of fashion, whereas fit is something that is pretty well-understood across time. Bitch, please.
I don't know if it is a question of whether they are in or out of fashion. Some people can pull off pleats, but when they don't look good, they really don't look good. If someone is reading this primer, they are probably not in a position to tell which is which.
A fair point. I suggest only that whether or not you can pull off pleats has a lot less to do with your build or any other personal characteristic and a lot more to do with the kind of pants you're wearing (and whether you are wearing them properly). (To be fair, if you have massive thighs, you basically have to have pleats; this is not an issue for most people though). And so as regards fashion, it's not a matter of whether pleats are in fashion, but how high a rise is fashionable.
If you wear your pants anywhere near your hips, you will look like a clown if you have pleats. Likewise, pants which were made to be worn near the hips are clown-pants if they have pleats.
If your pants, however, have a high rise, and you are man enough to wear them at your natural waist, then pleats will make it possible to sit _and_ stand in your pants and not look like a total fool.
Oh, you never go to weddings, funerals, dedications, meetings with old school customers, benefit dinners, graduations, award ceremonies, court, formal dinners or church?
Just because people are not required to wear formal clothing everyday does not mean they don't want to look sharp when they do-
A good reference for anyone encouraging "Formal Fridays" or something similar around the office. There's a lot to be said for the occasional break from the routine of t-shirt and jeans.
This is incredibly American centric and ignorant of variant weather conditions.
Try wearing a fit shirt, long pants and leather shoes in 90+ weather...
If you're cynical like me and think "dressing well" is a code word for "conform!", you can look at adopting the costume every once in a while (used judiciously) as a kind of hack that will get you what you want more often than wearing my normal uniform of loose shorts an old t-shirt and flip flops.
Knowing when to throw on a decently tailored suit, a nice shirt and a pair of well matched shoes (even if your screaming inside to kick them off after a half hour) has gotten me contracts, procurements, jobs, raises and let me get away with figurative murder quite a few times. It says "I'm part of this club, I'm playing this game, let's not let a few hundred thousand dollars come between us."
I hate suits and think they're a symbolic harness the modern world uses to remind workers they're one step away from either a hanging or working as a beast of labor, but using them as a tool to extract money from people is a perfectly valid tactic. In other words, I hate not making money more than I hate wearing a suit.
The problem? I'm personally built like a square, and when I was younger and in better shape it was even worse. Very little on this page is relevant for me. Years of kickboxing built up thick thighs and calves and makes slim cut pants look ridiculous, likewise a 17.5" neck means I might find a single Oxford at any given store regardless of style. Wide feet and high arches mean fine shoes feel like Chinese foot binding. Round or narrow tipped shoes look absolutely absurd on my frame, square toed shoes look far better and much more consistent.
Here's my hacks that end up looking decent if I need to:
Go west coast, no tie. Leave the top button undone. No shirts with button-down collars, those are meant for ties. Slip on wide square toed dress shoes with good grippy soles. Sleeve length and shoulder fit here are dead on (you wouldn't believe how many people aren't aware of how shoulders should fit). Never button your blazer or suit jacket -- keep at least one hand in your pocket for the cool "I'm a guy in a suit" look, everybody will be doing it anyway. A barrel chest and years of not kickboxing have given me a healthy man-gut no blazer fit will ever work with. Just make sure the shoulder and sleeve length is right and you'll be fine. I take the jacket off at the start of meetings anyway. If negotiations of lots of paperwork start, roll your sleeves up, it'll cool you off and make you look serious while working on this "hard stuff". Regular cut pants, no low cut, shirts don't like staying tucked in well. Being built like a square means coats below the waste are an absolute no-no. P-coats work well if you absolutely need a coat. Avoid pleats at all costs. Flat-toed shoes, round or pointy toes look absurd on my square body shape. Tuck your shirt in properly, and starch the collar. Nothing says "retail worker forced to wear this" more than shirts that aren't tucked in right or messed up collars.
To paraphrase the Romans, worship these gods in public for approval, abandon them in private for a comfortable life.
Just curious why you feel so paranoid about "conforming"?
I feel like until somebody tells you that you "must" dress some way, then anything else is just opinion that you may or may not agree with. There is so much anger directed towards the top post on this thread because he shares his opinions on mens haberdashery.
My bottom line is that when I wear a suit that fits me like a glove, when I have a crisp, clean collar stand up against the back of my neck, when I slip on a nice pair of shoes -- carefully crafted and made with great materials, the kind that will last you easily 20 years -- when I do all that, I always just feel so good about how I look and how I feel.
Sometimes a tie isn't comfortable. So sometimes I endure the discomfort for a specific reason, other times I just don't wear a tie. But I never bristle with the anger at 'conformity' so I thought I'd ask you.
What I recommend to get started is go to a consignment/thrift store such as Goodwill and liberally buying cheap clothes that fit decently well. For shirts this mainly just means ensuring the shoulder crease lines up with the "angle" at the end of your shoulder. Take them all to an alterations store and have the nice lady fit everything for you. This will be the most expensive part of this whole endeavor. As a result you'll get a better feel for the types of clothes that work best for you as well as how clothes are supposed to fit, all for relatively little upfront investment.
Also get nice shoes. Reddit's malefashionadvice is notorious for advocating Clarks Desert Boots. There's a reason for this; they're fantastic. I own a pair, wear them all the time. Whatever you do, don't wear sneakers around unless you're a personal trainer. You're probably not in high school anymore, and nice shoes will instantly help you present yourself more professionally.