The ultimate choice for a kick-ass and stylish outfit? A charcoal wool blazer with grey chinos. Introduce dress boots to the equation to instantly spice up the look. This one is an appealing pick if you're looking for a cool ensemble that will take you from summer to fall. As you're moving from your 20s to your 30s, you probably want to start dressing with more class. If that's the case, outfits like this are a never-failing option.