Wear a turtleneck and grey chinos if you want to look casual and cool without trying too hard. Does this ensemble feel all-too-perfect? Let a pair of white athletic shoes spice things up. This look is a viable choice when it comes to crafting a kick-ass look for unpredictable fall weather. Those who are curious how to sport edgy off-duty outfits as you step into your 30s, this combo should answer your question.