Edit (12/11/2015): Turned ‘resources’ into a reading list.
A couple years ago, I gave a presentation on Style/Fashion for Effective Altruists/aspiring rationalists, and I was quite happy with how it turned out. We recorded the first half, and you can find the slides here (short version here). We followed up the presentation with a trip to a couple of department stores, Nordstrom and Target, which turned out to be very helpful.
Follow up advice
For men, I recommend the following reading list (in reading order):
- My intro slides on fashion. Or the recorded presentation.
- r/malefashionadvice fit guide
- Primer’s fit guides (index after the picture). Especially shirt and pants guides.
- Basic wardrobe. Good as a set of Quest Items.
- Shoes: shoe style (instead of fit) is comparatively important, and guides are especially helpful here. This guide is really good.
- Button up shirts
- What are you wearing today? threads are a great source of pictures with commentary you can use to learn via reinforcement learning. Make predictions on how other people will judge each picture.
- r/malefashionadvice has many other guides on the sidebar. Some are excellent and some are not so good.
For women: read the first three, then I suggest looking at the guides on r/femalefashionadvice (though I do not have extensive personal experience here).