I'm always on a constant hunt for good clothes and a quest to be fashionable in them

I am NOT one of those baggy cargo short guys either. For one, when you're already short, things that are baggy tend to make you look short and wide and/or fat. I'm not one of the traditional haircut guys either. And yes - they were originally for work type or outdoor type activities ... don't know how they got so popular either.
Hair is a whole other topic really lol.
I do own a flannel shirt. Flannel shirts are not bad. They're basically just plaid shirts with different material. And plenty of hipsters and more fashionable men wear them.
I've found that most guys button down shirts are either a solid color, plaid or stripped. There is the occasional pattern but it's hard to find something that's not like some old man tommy bahama shirt or similar. Actually I'd love to know where Clinton Kelly (What Not To Wear) gets his pattern shirts because they're always ace!
Layering is certainly something I've found that works if done properly. I've been trying to pay attention a lot to other guys I know of that dress in a way that I'd be interested in as well as looking at a lot of sites on the web.
Generally, I think if you want to be "stylish" like I think you want to be you want to stay away from the baggy/oversize clothes, printing-disaster (those types of shirts where print is all over them), sports attire and those types of things. Sure those are all men's clothes and they work for a large portion of guys out there who don't much care about clothes but being "put together" takes a little more effort imo

Here's some other options I'm finding work once I get around putting outfits together:
1) Nice jackets
2) Blazers (not the normal type but more that fitted, European type)
3) ties, hats, belts, scarves, and other accessories
4) more fitted pants
5) dark wash jeans (or dark/black skinny jeans if you can get away with it)
6) hipster t-shirts (think
threadless.com, etc.)
7) button down shirts, sweaters, cardigans, fitted hoodies, etc.
8 ) pinstripes (pants, the more fitted shorts, etc.)
I've totally come up on some awesome stuff at thrift stores too. I found a black leather jacket (nice style that actually buttons as opposed to zips) the other day for under $20 that's pretty hip. I also scored a v-neck sweater. I've also found some cool barely worn black short boots not too long ago.
I should add to this some of the places I look to for inspiration are Details magazine and urban outfitters