A man wearing a graduation cap, a suit, and an orange shawl walks in front of city shops.
A woman wearing an evening gown is at a party.
A man and a woman are two different people. An outfit consisting of a graduation cap, a suit, and an orange shawl is different than an evening gown. City shops are not the same location as a party.
The first sentence is about a man and the second sentence is about a woman.
The person can either a man or a woman. The person is either wearing a graduation cap, suit, and orange shawl or an evening gown.