Yeah man, I start out by going to a high end barbershop that has really good reviews and just seeing what they recommend. Be straight up like "I wanna switch up my look to get more pussy". They will get it. In terms of clothes, the key thing is that they are form fitting. Shouldn't be too baggy. I personally like Zara and H&M. They both have served me well. You could also ask in either one of those stores, especially if you see an attractive girl what she thinks would be good. When I go out, I typically wear white pants and a black tshirt. I think that's a good look for the majority of the people. Generally, tshirts shouldn't have too much writing with designs on them