Nice clothing (http://www.makeyourownjeans.com/ to get custom-designed jeans that fit really well
This is pretty cool if it's legit, but something about it looks a bit sketchy to me. Particularly for the leather stuff; materials cost there is high enough that a $100 leather coat is pretty much automatically suspect. (Lower-quality and reconstituted leather can be that cheap, but they react very poorly to wear.) What's your experience with the site?
I have no personal experience with that site, but that's mostly because reddit's /r/malefashionadvice thinks they're terrible.
On ChrisHallquist's post extolling the virtues of money, the top comment is Eliezer pointing out the lack of concrete examples. Can anyone think of any? This is not just hypothetical: if I think your suggestion is good, I will try it (and report back on how it went)
I care about health, improving personal skills (particularly: programming, writing, people skills), gaining respect (particularly at work), and entertainment (these days: primarily books and computer games). If you think I should care about something else, feel free to suggest it.
I am early-twenties programmer living in San Francisco. In the interest of getting advice useful to more than one person, I'll omit further personal details.
Budget: $50/day
If your idea requires significant ongoing time commitment, that is a major negative.