Fashion isn't prioritized in many hyper-analytical circles. Many in these communities write it off as frill and unnecessary. They say they "just dress comfortably" and leave it at that.
To me, that seems like a huge blind spot. It misses a fundamental point -
A piece of clothing is fundamentally a tool.
Definitions are important so everyone is on the same page. I feel like Wikipedia's first sentence on "tool" accurately describes it -
A tool is a device that can be used to produce an item or achieve a task, but that is not consumed in the process.
Clothing clearly fits that definition of a tool.
Appropriately chosen clothing can keep you from freezing in the winter, from getting sunburnt in the summer, and can keep you dry in a rainstorm.
It can also help you achieve things involving other people. I think it's fair to draw a distinction between "clothing" and "fashion" based on whether your objectives involve interpersonal skills. If you're wearing clothing in relation to the environment and without other people, that's using clothing as a tool.
But clothing clearly can affect other people's opinions of you, willingness to accept your arguments, willing to hire or contract you, even their desire to associate with you. All of that is changed by clothing - or more specifically, your "fashion."
While most rationalists would happily and quickly plan out the best hiking boots to wear to not get blisters on a hike, or research the best shoes for bicycling or swimsuit for swimming, anecdotally many seem hesitant or even hostile to the idea of using fashion as a tool to achieve their objectives.
That's possibly a mistake.
The thing fashion can do best and most fundamentally is affect a person's initial first impression of you. Fashion is less important if you're in a context where you're guaranteed to get to know someone over a longer period of time, and is more important if you're going to get filtered quickly.
I propose that the most rational usage of fashion is this -
1. Ask yourself what your goals are in the situation you're about to go into.
2. Ask yourself what first impression would help you reach your goals.
3. Pick out and wear clothing that helps communicate that first impression.
The process is important. In isolation, there's no "good fashion" - it depends on your objectives.
In some circles, people more or less won't care how you're dressed. But even then, there's likely some clothing that will perform better than others. If you can afford the time or money to find clothing to fit your objectives, then there's no reason not to utilize this advantage.
I say "time or money" because you can deploy either - if money isn't an issue, there's stores where the majority of things look good, and the people there are professionals who will spend time giving you good feedback. Any high end department store like Saks Fifth Avenue, Bloomingdales, or a high end tailor fits this category.
Alternatively, you can deploy time. To do that, survey the people that most effectively communicate the first impression you want to convey. Take actual notes and look for common trends. Then, go find pieces that look similar. You won't be perfect right away, but like any other skill, with practice you'll rapidly improve. Incidentally, the marginal cost to produce clothing is incredibly cheap, so most fashion lines over-produce clothing and have to liquidate it at super-discount sale prices periodically. There tends to be a major "Summer Sale" and "Winter Sale" once per year that have high end clothing that 70% to 90% off, making the cost comprable to the mid-tier.
There's also "Sample Sales" where over-produced items are liquidated or when a designer wants to see the buying public's reaction to their new pieces. Again, ultra-high-end clothing can be purchased at discount rates at these environments. You can get basically any semi-standard piece of high end clothing for not very much money if you put in the time. My strategy in the past has been to wait until finding a great opportunity like that, and then buying 1-2 years worth of clothing in one swoop. It doesn't take much supplementing after that.
It takes very little cognitive energy to begin this process. Next time you see someone who strikes a very good impression, stop and analyze a little bit. Note what they're wearing. If you want to strike that same first impression, go get something comprable. Your fashion will be working for you at that point, and your interpersonal dealings will become easier.
I've been dressing to make an impression for years. In school and college I used to keep a collection of clothes that would allow me to "blend" with different social groups; so you would wear black and red and steel jewellry with the goths, take off the chains and add some plaid and you'd fit in pretty well with the punks. A ratty t-shirt and some baggy t-shirt and you could hang out with the skater crowd, or a number of the just-regular-joe people. It's really not hard. I used to challenge myself to see how many groups I could 'pass' with. I think I was only ever outed a time or two.
When I started interacting with people older than my peer group (aka, the adult world) I dropped "fashion" almost altogether. If you look like you pay too much attention to your clothes, older people think you are flighty.
Plus 'being fashionable' generally does not mean you are dressing to show yourself in the best light. (as evidenced by the number of people in skinny jeans who should NOT be in skinny jeans. Before that, recall how often low-riders worked for people).
It's true that "classic" wear is harder to find; Seb gives good advice, a higher end store will stock more (the upper class is more about being chic than fashionable) but if you know what you're looking for, you can find it.
And because fashion is cyclical, if you can wait until 'your thing' comes in and buy things that are unlikely to date. Until the last year, I had a hell of a time finding pencil skirts. I wear pencil skirts (or sheaths) almost exclusively because I am very short and curvy. Any extra material, flair or flounce makes me look chubby, but a classic pencil puts curves in all the right places. So I bought three pencil skirts this year. I look best in jewel tones; red and purple and blue. They've been in in the last few years, so I've gotten several blouses and scarves. And I can't wait until kitten heels come back in... stilettoes are fine, but not as practical for everyday wear.
All three of those "trends" will last a long time; they'll never be fully out of style, as long as you wear them well. There's the odd one that will look dated; I recently retired a red satin blouse because it had puffed shoulder sleeves that dated the look, and even that would have been fine except the trend is for muted fabrics (three strikes, in other words). And it's fine to follow trends if they work for you; leggings and tunics look ok on me, as long as I'm wearing pumps.
I realize after the length of this comment it will be hard to make my case that I'm not a girly-girl. In fact, I was in my second year of college before I even knew how to apply make-up. But when I realized I would soon be consorting with a much more polished crowd, I found a boutique that offered makeup lessons and I started paying much closer attention to, as Sebastian says, making the impression I wanted to make.
I disagree, Peter. The information does not date all that quickly-- particularly mens fashions. If you bought a very classic suit ten years ago, you would be able to buy a new tie and wear it tomorrow -- no one would be the wiser.
Certain things are fadish --tie widths and shirt collars come to mind. But business styles change slowly.
I took my partner out to get him tricked out. He had a white shirt and black dress pants and a black tie when he started. We got him a black sports jacket (acceptable in all but the most formal venues) and a pair of grey pants, and a red dress shirt and a blue dress shirt, and a tie that matched all three. That is enough basics to get through a round of job interviews or a week long wedding. In, say, 5-7 years, he may want to update the jacket.
The rule of thumb is up to two neutrals and a pop of color-- any color you want, as long as it looks good on you.
Certainly, there are things that are tougher to learn; the difference between European tailoring and American; how to make sure things fit right (off the shelf dress-wear is astonishingly poor fitting). To that end, I would recommend finding some classic styles (ask the salesperson to assist you, and do a google search before-hand so you have a basic idea) and find a good tailor. Classic, well-made piece will cost about 50% more than you are used to, and tailoring will add another 20%, but you will have clothes that make you look polished and confident.
Certain fashions may go out of style, but style never goes out of fashion. There are certain universal principles that are important in developing style - having well-fitting clothes, colors that complement your skin tone and each other, layering, etc. Those elements will never go out of style. While certain specific types of style may become outdated, there are many many aspects of fashion/style that will never be obsolete.
"You won’t be perfect right away, but like any other skill, with practice you’ll rapidly improve."
"It takes very little cognitive energy to begin this process."
I disagree that it takes very little cognitive energy to begin analyzing fashion. I would guess that its actually fairly hard for your target audience to start noticing fashion details without someone continually pointing it out to them over a long period of time. Fashion can certainly be frivolous. But its a game/skill as you point out. And many people are horrifically bad at that game. So they rationalize away their incompetence by saying the game was stupid to begin with.
Another reason to study fashion is that scholarship is a virtue of rationality and if we interpret that virtue in a broad sense, it includes studying fashion. While fashion is not a scholarly discipline, there is still as large amount of information that goes into good fashion choices. Such knowledge is often related to facts about human anatomy, perception and biases. As fashion changes very quickly, much of the information is time sensitive - what is cool today is dated tomorrow. But there is still some important information, such as how to artfully conceal flaws, that is timeless.
After having it recommended to me for the fifth time, I finally read through Harry Potter and the Methods of Rationality. It didn't seem like it'd be interesting to me, but I was really mistaken. It's fantastic.
One thing I noticed is that Harry threatens people a lot. My initial reaction was, "Nahh, that wouldn't work."
It wasn't to scrutinize my own experience. It wasn't to do a google search if there's literature available. It wasn't to ask a few friends what their experiences were like and compare them.
After further thought, I came to realization - almost every time I've threatened someone (which is rarely), it's worked. Now, I'm kind of tempted to write that off as "well, I had the moral high ground in each of those cases" - but:
1. Harry usually or always has the moral high ground when he threatens people in MOR.
You only get one chance to make a first impression.
We see the importance of appearance in direct association to leadership in many ways. We have an archetype of the way God or Jesus dress, there's the story of the Emperor's New Clothes. Though that story teaches another lesson, it is interesting to think that how a leader looked was so important to him, he went out in the streets in front of all his subjects stark naked. How we present ourselves is as important to feeling like a leader as it is to the outside world. While their are deviations from the norm, for example Steve Jobs' black turtleneck look, your presentation can be the first expression of leadership you do you make.
What you wear and how you look is so important that the Wall Street Journal has a regular feature titled Work Wear.In this feature they follow the fashion cultures of leading corporations and their employees. At Foursquare they wear t-shirts, it's expressively business casual at Yahoo, anything goes at Martha Stewart Omnimedia. (WSJ, n.d) They also wrote an article just about the way mogul Thomas Barrack dresses, stating that, how he dresses "is more of a tool than a trend." (Binkley, C. 2007) He dressed differently for each locale, ties his scarves in a particular fashion, and wears red ties for luck.
In an overview of world leaders and the garb they prefer, there is a running theme of national traditional wear, military uniforms, and suits - symbols of authority and connection to one's realm of leadership. Though, some leaders have a flair for the fantastic like the previous Pope Benedict's pension for Prada or Muammar Gaddafi being known to wear elaborate outfits. It was even reported that the New York Times received a purported Gadhafi government request for help in organizing a Metropolitan Museum exhibition of the dictator's "four decades of superior dress sense." (B. Neild, 2011) It is obvious that even on the world stage how one dresses equates to their position.