Demonstrate your chops in men's fashion in this modern casual pairing of a black crew-neck t-shirt and black and white vertical striped chinos. Put an elegant spin on your outfit by rocking black leather chelsea boots. Now that's what we call a knockout cold weather ensemble. As you're progressing through your late 20s, you want to start dressing more like a mature gentleman. In this case, outfits like this are perfect as inspiration.