Good thread. For me, I always knew I had no idea what I was doing in terms of clothing and dress. For many years I never spent much thought on clothing. I just wore the same things all the time, year after year--flannels, levi's, t-shirts, sweaters, thrifted outerware, etc--replacing it (or allowing it to be replaced) during birthdays and christmas. To be honest, I occassionally look back on that innocent time with a little nostalgia. I simply didn't think much about clothes. When I really started making 'off' decisions, though, was during a period when I wanted to improve my look, became willing to spend money to do so, but still didn't know anything about what, when, where, or how to buy. I didn't know how to coordinate, either, so even if through sheer luck i landed a genuinely nice pair of shoes, i had no idea how to wear them. More often than not, the stuff I acquired was just not good. Worse, it fit poorly. Among the many bad purchases I made during this period were some black dolce and gabbana corrected grain plain toe bluchers that were pretty clownish, and just a lot of suit jackets and crap that, to my eyes, signalled 'dressing up' but were too big for me. I could try on a jacket sized anywhere from a 40 - 42 (i'm a proper 38) and if it 'hung right' and i liked the color i would buy it. The I'd take it home, without any tailoring, and hang it in my closet. Now and then I'd take it out, throw it on, and try to dress up an "outift", maybe pairing it with an ill-fitting button down and my d&g's. I'd be trying really hard to look cool, well-dressed, and grown up. Yet even my own untrained eye could see I looked like a douche-bag. Since I couldn't fool myself, even, I stripped the stuff off and reached for my old jeans and T's and sneakers before heading out the door. This was a frustrating time in my, uh, sartorial development, as I was now spending time and money on clothes, but with no apparent pay-off, because they looked foolish and contrived, and I didn't wear them. The (obligatory) turning point came when I started to actually seek out information. I read some books, magazines. Developed a casual but persistent interest in the history of shoes and clothing. Just started to pay attention, I think, and to notice clothing. I still made purchases, and still made mistakes, but I was trending in the right direction. I discovered SF quite a bit later, when I at least had a bit of a handle on how to acquire, edit, and dress. The arc I've described in similar to many people on these boards.