This combo of a grey short sleeve shirt and charcoal skinny jeans is undeniable proof that a straightforward off-duty look can still be really sharp. Black leather casual boots are guaranteed to bring a touch of polish to your look. When leaves turn yellow and red and fall settles in, you'll love this outfit as your go-to for transeasonal weather. Gentlemen wondering how to dress well in your late 20s, you have your answer.