A lot of fashion starts off a little intimidating. As guys we have an idea of what is well dressed. The problem is that when we think of what well dressed looks like there is a specific idea that comes to mind. His pants aren't too loose or too tight, he's wearing black, and his shoes have a high polish.
The problem is this, every man is different. We don't all have thick black hair, and a square jaw. This isn't depressing, think about the perfect woman. Guarantee its different from your best friends idea. Thus the same might be true of women. The goal then is to be the most fully you that you can be, knowing that you are somebodies ideal guy. Think about Steve McQueen... the man was the ultimate badass! On the complete other side of the spectrum look at George Clooney. These guys are so different, but women love them both.
Think about your favorite pair of shoes, your favorite shirt, your favorite jacket. What is it about this that makes it your favorite. Is it sentimental value, or that you've worn it so many times that it just feels perfect, or is it the color or texture. Sometimes its the feel... Next time your near a nice clothing store ask a clerk to show you the difference between a plain wool sweater and a cashmere sweater. Its unbelievable!
Often times its the color, I have this dark olive shirt, and I just feel like its the absolute best color ever made for me. If its the comfort of the shoes, build on that. This is all about getting to know who you are. I think people try so hard their whole lives to not get put in a box, but the problem is that they just don't have an identity then. I like to think of it simply as "I own my box!" I'm the master of my identity. I have the power to sort out what a Zach thing to wear is.
For instance I've discovered that I love paisley, and argyle. I just do. Now I have a friend that loves t-shirts, specifically band shirts. And he rocks them! He started to wears jeans and a pair of vintage Vans and many of our female friends love it. He has this carefree artistic attitude, I'm pretty sure that he's had a days growth on his face for three years. Now the thing that a lot of people do wrong is that they begin to let their style go. They keep the same five band shirts for ten years, and its no long fashion, then its just laziness. You have to keep up with yourself. Keep seeing whats out there, and what your next favorite shirt is going to be. My mom has this idea that she's going to make quilts for us kids out of our old favorite shirts and pants. This is brilliant in my mind because you get to keep your favorite shirt, but your girlfriend doesn't have to dread you pulling it out of the closet.
I have this thing that I do every season. I go through my wardrobe and find my favorite total outfit from the last season, and I wear it when I go shopping for new clothes. It holds me to a high standard. Have you ever put on a pair of slacks right after your favorite pair of jeans? It feels horrible, they're stiff, and so not you. Your favorite jeans don't lie. It helps you to gauge everything, by what is ideal in your world. If you feel out of place in a store in your favorite outfit, don't bother shopping there.
Remember that every person you meet will be judging you by what you wear, but the only person that really matters is you. Keep up with yourself and you really can't go wrong.
Oh... and one more thing, I never wear all of my favorite items together more than once a season. You've gotta keep it interesting.
