For me this is a problem. At least because I understand that people always judge by appearance first. Especially when it comes to dates. I want to look cool and stylish, but how? I do not know how to put outfits together at all.

Your visual exposure solves everything, man. If you do not understand how and what to combine, just look at how others do it. Now there are social networks, Pinterest, and you can simply look at what people wear on the street, what catches your eye and all that. It works, it just takes time.

I do not stress about it. My personal comfort is more important to me and I do not really bother about style, fashion, trends. I have no idea if flannel shirts are in fashion right now. Maybe not, but I will definitely buy myself men's Sullen flannels for winter because that is literally the best clothing for cold weather. Flannel feels really nice on the body and it actually keeps you warm. And with jeans it is always a basic combo that looks good.