Okay it's been a while since I've been on this but I'm actually terrified to try out new outfits and styles, I practically live in jeans and casual tees, can anyone recommend a new style or types of clothes I could try?

Is this is a phobia, or just a dislike of trends and fashion?
What's wrong with jeans and tees? Are you unhappy?

As opposed to the empty heads that spend ALL their income on the newest fashions as they come out.. Only to toss them aside long before they are worn out just because they are no longer cutting edge fashion? THOSE are the people that have the problem, not you.

Why? Why should you try and wear clothes you do not like?

Unless you need a certain look or style for work.

I wore mostly the "dickies" style work pants or sweats for years with a pull over shirt.

No need to follow the latest trends. They're trends only for a moment, and they're trends only because brainless people that have no style of their own, follow all the other sheep.

You sound like you have it figured out. If you're happy in jeans and t-shirts, than why change your style? If you want to change your style, find things you like, don't ask anyone else to dress you. Be yourself!