There are a number of references to the attire Jay Gatsby wears throughout the novel. Each, in its own way, points to or is associated with the particular event in which it is mentioned. At first, there are hardly any references to Jay's clothes. On their first meeting, Nick Carraway does not even realize that he is speaking to the famous Mr. Gatsby.
We were sitting at a table with a man of about my age and a rowdy little girl, who gave way upon the slightest provocation to uncontrollable laughter.
His clothes are not mentioned at all. It is clear that Jay wore attire which did not draw too much attention to him. This fits in with the anonymity of his persona. It retains the mystery surrounding him, which obviously led to many rumors and much gossip.
In this chapter (three), Nick gives us an idea of what Jay wears. He mentions
...I was looking at an elegant young rough-neck,...
The oxymoron tells the reader that Jay was well-dressed and looked smart, fitting attire for a man of wealth, but that he had an air of roughness about him. There was an edge to Jay Gatsby which reflected the harsh conditions which he had to endure.
Fitzgerald develops Jay Gatsby's character by consecutively, although not necessarily in chronological order, describing the stages through which Jay's dress evolves.
In chapter four, Jordan Baker describes her first meeting with Jay:
...she was sitting in it with a lieutenant I had never seen before.
He was obviously wearing a military uniform for her to recognize his position. This description informs of a point in Jay's life when he was about to leave Daisy to do military service during the war. At that point he had nothing to offer her in material terms.
In chapter 5, Nick had arranged tea for Daisy. This was a ruse so that Jay could meet her. It was a carefully planned, secret liaison. The clothing Jay wore for the occasion is symbolic of how he wished to present himself to his lost love, his holy grail. He went somewhat overboard, as the description shows:
An hour later the front door opened nervously, and Gatsby, in a white flannel suit, silver shirt, and gold-colored tie, hurried in.
The colors are significant, since they denote richness and the value of the occasion for Jay. It was to be a moment of great value, indicated by the colors silver and gold. Later in the chapter, Jay displays his grand possessions. These are an indication to Daisy that he has made it and will be able to take care of her material needs, just like Tom does.
...opened for us two hulking patent cabinets which held his massed suits and dressing-gowns and ties, and his shirts, piled like bricks in stacks a dozen high.
Jay, once again, wants to prove his status and confirm his value. He states that,
“I’ve got a man in England who buys me clothes. He sends over a selection of things at the beginning of each season, spring and fall.”
In the same chapter, we are given insight into Jay's humble past, just after he met Dan Cody.
There was a small picture of Gatsby, also in yachting costume, on the bureau —
Furthermore, Jay has now become very comfortable and happy and has changed from the almost garish silver shirt and gold tie and was:
...now decently clothed in a “sport shirt,” open at the neck, sneakers, and duck trousers of a nebulous hue.
The clothes he wears here indicate that he is at ease. The anxiety he had experienced before is all gone. He feels comfortable and happy for Daisy has given him a reason to be so.
Chapter 6 tells of his meeting with Dan Cody and the description of his clothes before this time indicates the harsh life he had to endure.
It was James Gatz who had been loafing along the beach that afternoon in a torn green jersey and a pair of canvas pants,...
Jay was dirt poor and survived "as a clam-digger and a salmon-fisher or in any other capacity that brought him food and bed."
At any rate, Cody asked him a few questions (one of them elicited the brand new name) and found that he was quick and extravagantly ambitious. A few days later he took him to Duluth and bought him a blue coat, six pair of white duck trousers, and a yachting cap.
The clothes here symbolized a new way of life for Jay. A new opportunity had arisen for him and he could achieve his ambitions.
In chapter 8, after the accident in which Myrtle Wilson was killed, Nick describes Jay's attire as follows:
His gorgeous pink rag of a suit made a bright spot of color against the white steps, and I thought of the night when I first came to his ancestral home, three months before.
Once again, a contrast is created. The words "gorgeous" and "rag" form an antithesis which indicates Jay's confused state at that moment. He is unsure of what to do. Irony is created by the color pink, which represents hope, but it is clear that this bright hope has been damaged. Against the white steps it becomes glaringly obvious that there is nothing more, no turning back.
In chapter nine, Jay's vulnerability is effectively portrayed by what he wears:
At two o’clock Gatsby put on his bathing-suit and left word with the butler that if any one phoned word was to be brought to him at the pool.
Jay is unprotected and vulnerable to any attack. It is at this point that George Wilson, husband of the tragically unfortunate Myrtle, arrives and shoots Jay, killing him.
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