Marry a blue denim jacket with a crew-neck t-shirt to demonstrate you've got serious menswear prowess. You can take a more relaxed approach with footwear and grab a pair of brown leather work boots. When it's one of those bleak autumn days, sometimes only a kick-ass ensemble like this one can get you out the door in the morning. Now that's a fun look that will surely make you stand out among other mature fellas.