You'll be surprised at how easy it is for any gentleman to get dressed this way. Just a red plaid long sleeve shirt and navy jeans. A trendy pair of tan leather casual boots is a simple way to upgrade your ensemble. Seeing as it is getting colder with each day, this ensemble seems a viable idea for in between seasons. As you head into your 30s, you probably want to start dressing maturely. In this case, getups like this are perfect as inspiration.