I‘ve tried to do outfits like this before but unlike him, my boots and cardigans aren’t as nice.
Me: Where did you get your boots?
Him: Oh, Calvin Klein.
The difficult thing about finding a fashionable boot is trying to get something slim yet simple. If you can manage to find something within your price range the payoff is great: you can tuck your jeans inside for a casual look and you can also wear it normally as a more dressy boot.