I'd love to stay fashionably dressed. As it is though, I just can't afford it. Or, I'd rather spend my money on something else. How much do you spend to buy the current season's clothing? And what's the best way to get it? I'd love to have a website where I input my basic style preferences or rate different fashions of the current season and get output of links to buy in style clothes/outfits I would like in my price range.

This is true, it is quite expensive to stay in touch with fashion. However, it's not so hard to find things that look good on the cheap. I typically try and bargain hunt at stores such as H&M, tjmax, and the sale section of large department stores. If something is a season or two old - it's good enough to wear around without anybody chastising you for it. It's really not WHAT you wear, but HOW you wear it.

Most basics stay in fashion for about a decade.

"I just pay $12/year and subscribe to "Nylon for guys" magazine"

You may be a hipster. http://www.urbandictionary.com/define.php?term=hipster

"Listens to bands that you have never heard of. Has hairstyle that can only be described as "complicated." (Most likely achieved by a minimum of one week not washing it.) Probably tattooed. Maybe gay. Definitely cooler than you. Reads Black Book, Nylon, and the Styles section of the New York Times. Drinks Pabst Blue Ribbon. Often. Complains. Always denies being a hipster..."

Had the jeans. Had the kicks. Had the day-glo. No mullet. Was that the problem?