Dress for the situation but wear high quality clothes with the right fit. Just because its business attire doesn't mean its good clothing or that you're dressed well. Stand outside the local courthouse at lunch time and watch all the dumpy ill-fitting suits pour out and you'll see what I mean.
Fit and Quality are far more important than type of clothing.
One of the worst fashion sins are cheap ill-fitting 99$ suits. Man...
My recommendation guys, buy some nice shoes and a coat.
I'm still mystified as to how people decide that one piece of clothing "goes" with another, or looks bad with such-and-such.
Embracing new things can be intimidating and downright scary. I remember the first time I heard about the benefits of lifting weights, I was apprehensive. I thought I could just call others 'meatheads' and use my advanced degrees in computer science as a shield. But life does not work like that; we must continuously improve ourselves, in all aspects of our lives: social, personal, physical, intellectual. Learning to buy clothes and put together outfits is just another part of growing up, just like learning how to work out, or how to apply design patterns to a programming project.
On a more practical note, there are tons of resources on the Internet that can help you with figuring out what 'nice' clothes are, or how to put together outfits. Maybe start with this: http://www.kinowear.com/blog/science-of-style-introducing-th... . Or check out reddit's r/malefashionadvice guides, or maybe go on styleforum.net, or try putthison.com . Good luck!
Yes, you should wear clothes that fit. For instance, if your suit is too large, it will make you look clumsy. Rather than buy a suit for 99 bucks, I'd rather buy a good quality shirt. Invest in quality, I guess.
Secondly, I think you should wear clothes that make yourself feel comfortable not just because they fit from a physical point of view. They should be appropriate to your persona, don't wear something that you are not.
Also, men's fashion has deep roots in tradition and function. For example, did you know that the little holes on wingtip shoes were originally added to allow the water drain out when you were walking in the country? That history is part of the reason that wingtips are considered "less formal" than plain-toe shoes - they were meant for wearing in the country. I find that kind of thing interesting, it's not all about superficiality.
If you're really interested in learning these things you're in a golden age, there are a ton of people sharing information and ideas about men's fashion online. http://reddit.com/malefashionadvice is a good starting point.
I've made countless attempts at fashion over the past 20 years, but it's always ended in failure. The fact that people say my father dresses poorly (and I can't tell why) has been incredibly discouraging.
Another poster mentioned that striped shirt with striped pants is a no-no. Why is that? Also, why are certain colors considered to "match" and others not? It seems completely arbitrary.
In terms of colour matching, that's more of a personal thing. The biggest thing you need to remember is don't put a brown item next to a black item (ie brown shoes with black pants). This post on reddit covers the basics: http://www.reddit.com/r/malefashionadvice/comments/ginj6/in_...
As with all aesthetic disciplines the rules are made to be broken, but it's good to know them first.
Ok, so he mentions "warm" and "cool" colors. Since I burn within 30 seconds of encountering the sun, I'm "cool".
Then he mentions seasonal colors, all of which he says go with "cool" complextion, which means any color goes with cool? I think I'm missing something here.
I had someone once tell me I should wear "autumn" colors, so all of my stuff is yellow, orange, and brown, but apparently that doesn't work (or at least not always... There are some browns that work and others that don't apparently).
My eyes shift between light blue, green, and grey depending on the season. So that means I should wear those colors, right? Are my eyes considered to be "contrasting" or "non-contrasting"? How do you even decide what colors are "contrasting" or not?
Some other things:
"Blue shirt + yellow tie is pretty classic, but disastrous if done wrong. A deeper,darker yellow more akin to goldenrod and a lighter blue is the ticket here." - Is there an official matrix of acceptable color combinations available somewhere?
"Anything black at all should be a rough texture." - And yet I see so many people wearing smooth textured black things. Are they just poorly dressed?
"Grey flannel trousers are the shit" - Umm... ok. Why?
"One madras element per fit." - What's a madras element? Google didn't turn up anything useful.
"Be cohesive and holistic. The whole should be better than the sum of the parts. Build an outfit, don’t just toss together flair." - Great, but HOW do you do that?
"Don’t be overly matchy. “Close enough” is more charming and better looking than fabric shade OCD." - So don't wear colors of similar shade, then?
- Casual: Dark blue jeans, nearly any colour shirt, brown leather shoes - Charcoal slacks, black leather shoes, nearly any colour shirt - Khaki chinos, light blue shirt, brown shoes
>"Grey flannel trousers are the shit" - Umm... ok. Why? Because epicviking thinks so. I happen to like them too, they've got a great texture and they go with almost anything. You can wear black or brown shoes with them and any colour dress shirt pretty much.
>"One madras element per fit." - What's a madras element? Google didn't turn up anything useful. Madras is like a big plaid pattern.
>"Don’t be overly matchy. “Close enough” is more charming and better looking than fabric shade OCD." - So don't wear colors of similar shade, then? Try to avoid it yeah.
>"Blue shirt + yellow tie is pretty classic, but disastrous if done wrong. A deeper,darker yellow more akin to goldenrod and a lighter blue is the ticket here." - Is there an official matrix of acceptable color combinations available somewhere? Nope but if you're in a bind you can always google "what colour tie goes with a ____ shirt" and get some input.
If you want advice specific to yourself I'd post a picture of yourself on malefashionadvice, people there are very helpful (although you have to be okay with getting criticized, don't take it personally)
"Second, how often are you putting together complex colour profiles?" - What would be considered a complex color profile? I have a closet with clothes of various colors, and I need to choose which shirt to wear with which pants/shorts/whatever. And I guess which shoes. So I know that not all reds are the same, and not all oranges are the same, and some reds go with some oranges. Problem is I don't know which is which; That's why I was asking about a color matrix.
Then there's patterns, which are even more dangerous, because it seems that most mixes of colors don't go at all with most other mixes of colors. I don't understand how people decide that certain ones "match" and others don't. If there's no color matrix to show what works and what doesn't, how can you even know?
Probably because it made no sense! What I MEANT to type was "Fit is KING and much easier to understand."
Don't worry about a colour matrix, just try to buy clothes that go with everything. Nearly everything goes with dark blue jeans. Nearly everything goes with grey flannel slacks. Most things go with khaki chinos. I wouldn't try to match patterns but there's really no need to. How often do you really need to wear more than one patterned item at a time? Or even more than one coloured item at a time (not counting neutrals that go with everything like greys, beiges, browns, and really dark blues)
However, all of that aside none of it matters if your clothes fit poorly. Most 'bad dressers' are just wearing clothes that are far too big for them.
"Fit is KING and much easier to understand." - Ok. I've ordered a copy of "Gentleman: A Timeless Guide to Fashion". So hopefully that will explain fit.
If your face is ashen gray and pale because you are a programmer who hates the sun with an icy passion, wearing a black shirt will only accentuate your paleness. If you wore a white shirt, people would notice it much less.
If you're in good shape, you can find t-shirts and jeans that look pretty good, but even that isn't easy. If you're out of shape, it's nearly impossible. Conversely, oxford shirts, sports jackets and trousers have about 100 years of evolution in providing a good fit for all kinds of men's body shapes, and they're also far more amenable to alteration by a tailor (does anyone actually tailor their t-shirt?)