You’re looking for a peacoat, trench, or even a denim jacket (though personally I despise denim). I’d consider basic colours like black or tan. Black leather jacket is a classic product that can hardly go wrong with any other apparel. But in my opinion a black jacket with jeans option is too appealing, and ever trendy fashion. I do, I like the New York Giants Fear The Future Shirt but I will buy this shirt and I will love this look. Especially with a fitted black turtleneck underneath… If you don’t zip it up all the way you can easily wear it in summer. Totally, you can wear whatever you want. But it totally depends on you’re personal style, that’s the beauty of fashion! Personally I would go with black jeans+ black trench+ white converse. Which would be a more chic, street style look. I like to come off as classy and casual with my outfits, so I go with uniform colour and high contrast, or statement pieces. Which in your case would be your cool casual sneaks.