That's a good question, because this forum has played a large part in the education process. As an entrepreneur, you have a need for good clothing at times, but often can't afford it during the building process. My strategy was to have a go-to suit for the investors and whatnot, but otherwise not pay any attention to it - jeans/tshirt/sweaters/whatever-on-feet - typical software developer uniform. Relatively recently I noticed, and others noticed, that my words carried more impact with customers and investors when I was dressed business-ready. I made a conscious decision to dress better, this started with a trip or two to Joseph A. Bank, where I thought I was getting a good deal and good clothes. As it turns out, the sales staff sold me suits that were too large by a size. I didn't realize this for some time of course - but even doing that and beginning to wear nicer clothes started the 'bug'. Shortly after that, I massively rearranged my closet, gave racks of clothing away to Goodwill. That was phase 1 - realizing the need, spending a $1500 or so on mediocrity and finding a new hobby that I could really sink my teeth into.
Phase II - reaching out for style information. I started with GQ. lol. Almost turned into a fashion victim with that choice, but occasional browsing brought me to places like putthison.com where I started to get more enlightened. That browsing also brought me here, where after a time I started to recognize that there were some real pros giving great advice and showing off stylish outfits. Clothes in brand names I'd rarely heard of. At that point, the hill seemed really steep, primarily because of my location (hard to get to stores that carry these sort of things), a new language in the numbers involved with sizes and the recognition that people here were dealing in centimeters and debating collar styles and terms like 'waist suppression' (wtf??)
Phase III - acceptance and experimentation. In this phase I had to get used to the idea that you get what you pay for. Shoes? OK... *gulp* I dropped some cash on a pair of cordovan AEs and black captoe Bruno Maglis. The whole time I was kind of shaking my head at the prices, and of course I was paying straight up retail. In this phase I found my way to ebay and cautiously began dabbling in used auctions. I made some mistakes along the way, but none *too* expensive. It was here that I learned what 'fit' meant and discovered that my initial Joseph A Bank trips were based on bad sizing information.
Phase IV - learned how to skate! OK - after figuring out how to buy clothes online, being plugged into communities like this and having a brand new vocabulary in patterns, fabrics, brands and fitting concepts I began sinking a more serious level of funds into my wardrobe. This all had to do with the confidence that an education in the subject matter brings. I had learned the difference between fashion and style. I had also learned that opinions in style vary widely and there are only a few 'true rules'. I became deeply familiar with why those black sport coats were a bad idea. I payed more attention to things like belts and socks. I began to notice the little details of what people were wearing on TV and out in public. I did another round of closet cleaning, a lifetimes worth of bad shoes disappeared along with the complete destruction of the vestiges of my 'software developers uniform'. There was little choice, no room left in the closets for the mistakes of days past.
Today, I feel like I've got a respectable wardrobe and the confidence to wear it proudly. The vast majority of my education that brought me to this point occurred right here at styleforum. I have yet to have an article of clothing actually made for me. I'm sure I will in the future, but my bank account just can't take the activity that would surely follow an experiment in bespoke tailoring - another round of closet cleaning! Yet...