For an outfit that's street-style-worthy and casually classic, choose a charcoal blazer and a white and navy vertical striped dress shirt. Complement this look with navy leather derby shoes to instantly spice up the look. As you can see here, this combo is a really smart option, especially for awkward transition weather, when the temperature is starting to drop. A reliable option getup appropriate for gentlemen in their 20s who like to dress more elegantly.