How about a new style challenge?
Post a picture of how you are dressed for going to work/going out and have others critique it?
This is what I am wearing today at the office and similar to what I wear when going out socially as well. Dressing is pretty simple, especially for a man. For me I think my plan is to just get things that fit you. If you don't know, go dark and plain to be safe. It doesn't matter from where or how much it costs.
Blazer - $100 (Zara - was a full suit but I separated it from the dress pants as the office is casual now)
Skinny Jeans - $20 (Winners sale rack)
Plain long sleeve shirt - $7 (Walmart clearance)
Shoes - $8 (Walmart clearance)
Casio G-Shock GWM5610-1 - $150 (Amazon)