You can look awesome without trying too hard by opting for a v-neck sweater and black chinos. Put a different spin on your look by wearing black dress boots. As you can see here, it's extremely easy to look on-trend and stay toasty when chillier weather hits, thanks to this look. As you turn 30, you want to start dressing like a grown man. That's when outfits like this are a life saver.