In regards to running shoes and trainers, it's all about knowing how fashion works and what you can pull off, then you can start pushing boundaries and developing your own style. The people talking and blogging about what's in and what's out are normally speaking from the perspective of the outside looking in. As much as they would like to think they know what they are talking about, the majority are in no way trendsetters and regurgitating what they've heard somewhere else. The Nike Air Max is an iconic shoe for a reason. The Reebok Classic, Adidas Superstar, Air Force 1, etc have been around for decades for a reason and its definitely not because they are great trainers. The key with trainers are staying away from wider leg openings, as well as the proper inseam lengths and knowing what's appropriate for the occasion. The more tapered the leg of the jean, the better they work. Moto's, slims, some straight legs, that dont excessively stack or bunch up at the ankle, etc. When building your wardrobe, buy things that are versatile and that you know you can throw on any day of the week and look good, then start experimenting with edgier looks.