So many people have no idea how to dress, so congratulations to you to take the initiative! Being shy can be difficult, but you can get your shell a little confidence simply dressing. You are 100% correct about any method does not work for everyone. I do not think you should go in the “trendy” route per say. Go classic cuts that flatter your body type. Some basics you should start with a pair of dark-wash straight-leg jeans, a pair of black dress pants, tan dress pants, dark button-up shirts, a nice fitted sweater (no, not the tight turtleneck ones — - opt for a more flexible), and some, like all the days of dress shoes brown boots.
When you enter a store, look around before you do anything else. If you look at the clothes and think: this is not for me, then go ahead. http://www.shopwiki.com.au is a large online store bases that are a little more relaxed. They have nice khaki pants and jeans, and a bit of fun buttons shirts. Men’s clothing Express is another store I recommend. Here you will find dressier, that dress in black and beige pants, and some dressier tops.
Do not be afraid to ask sales for help - that is their job and you’ll probably save them the boredom of standing with nothing to do. First, look around the whole store. If you find something you want, try it, or ask a seller if he thinks it works well for you, and what to wear with it. They will be happy to help you, I promise.
And the most important thing is to try everything! Make sure it goes before buying clothing (ask a trusted friend or a seller).
For the basic wear everyday, I always love guys in nice fitting jeans (not too short or too tight and something with a dark wash). Avoid really light wash Levis. They are not flattering on anyone. For dressier pants, a nice khaki pant is always good. For them, it is worth spending a little money because you’ll have more wear on them. So they must be very good.