Why not go for a biker jacket and a black fit and flare dress? Both of these items are totally comfy and look incredible when matched together. On the footwear front, this ensemble pairs brilliantly with black leather knee high boots.
Black Fit and Flare Dress with Biker Jacket Smart Casual Outfits In Their 30s
For something on the casually cool end, choose a biker jacket and a black fit and flare dress.