In chapter 5 of The Great Gatsby, analyze the symbolism of Gatsby's shirts.

Gatsby's shirts represent his wealth. For Daisy, they might represent how far Gatsby has risen in society and how she missed an opportunity for happiness by not marrying him.

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The shirts symbolize the way Gatsby is trying to impress—to buy—Daisy with his wealth. He believes that his money makes him worthy of her love. As he tosses out beautiful shirt after beautiful shirt in all the colors of the rainbow, he is signaling to her that he can now meet her in terms of affluence.

The whole encounter has been carefully staged from the start to impress Daisy. Gatsby wants to meet her in Nick's more modest home so that he can wow her with his mansion only after the first shock of their reunion has ended. He has Nick's lawn mowed before Daisy comes. He quickly takes her on a tour of his grand mansion. With the shirts, Gatsby, who was impressed with the careless ease with which the younger Daisy took her affluence for granted, can finally offer her what appears to be limitless wealth.

Of course, the efforts he goes to and the way he throws out all his shirts before her show that wealth will never come effortlessly to him. He will always have to show it off to confirm through other people's eyes that it is real. He will always try too hard.

Daisy is overwhelmed, as her crying into the shirts indicates, and also not in touch with her feelings, as her inability to explain her crying suggests. By asking her to accept him on the basis of his wealth, on what he can offer her materially, Gatsby does show he understands her. Ironically, however, he is competing on a field where he can't win: Tom's old money and higher social status will always be more attractive to Daisy.

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While giving Daisy a tour through his mansion, Gatsby eventually shows her his shirts, sent to him each season by a man in England. Gatsby is proud of the shirts because they represent how he can afford to be stylish. They are a mark of his social ascension.

Daisy famously weeps over the shirts, burying her head in a pile of them. She claims it is because she has never seen such beautiful shirts in her life, but the truth is likely that she is sad that she did not wait for Gatsby. Unlike the philandering Tom, Gatsby is a man who adores Daisy and has been obsessed with her for years. For Daisy, the shirts represent a lost opportunity: if she had waited for Gatsby to make his fortune, then the two of them could have been married and possibly happy.

Of course, the fact that Gatsby and Daisy's possible union is represented by a pile of flashy shirts suggests their love is little more than a superficial show. Gatsby and Daisy are more enamored with images and ideals than they are with real people. Gatsby views Daisy as a representation of the wealthy, upper-class world he longs to fully break into, and Daisy views Gatsby as a romantic escape from her dull, sad life; but in the end, Daisy will not leave the security of her marriage with Tom for Gatsby, no matter how many nice shirts he accumulates.

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In chapter 5, Jay Gatsby takes Daisy on a tour through his home and shows her his closet full of elegant, expensive clothes. Gatsby mentions that he has a man in England who sends him new clothes at the beginning of each season. Gatsby then begins to throw shirt after shirt onto a pile as Nick and Daisy watch in amazement. Daisy becomes emotional and is overwhelmed by Gatsby's display of wealth as she puts her head into the shirts and begins to cry. Daisy submerses herself into Gatsby's clothes and says,

"They’re such beautiful shirts...It makes me sad because I’ve never seen such —such beautiful shirts before" (Fitzgerald, 59).

Gatsby's shirts symbolically represent his superficial nature and emphasis on appearance. Both Gatsby and Daisy value external appearances over substance and character throughout the novel. Gatsby's arrogant display of wealth and Daisy's overreaction to the expensive shirts reveal their true character and emphasis on material wealth. Similar to Jay Gatsby, the clothes represent his attractive exterior, which covers a corrupted, troubled soul. Like Gatsby's extravagant lifestyle, the shirts are simply for show and worn to impress others. Unfortunately, Gatsby's focus on material wealth will never equate to a meaningful relationship or true happiness. Like Gatsby's expensive shirts, which will deteriorate in time, his superficial relationship with Daisy will eventually end.

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The shirts symbolize Gatsby's wealth and demonstrate his rather ostentatious style. When Daisy looks at them all, she is overwhelmed and brought to tears. 

The shirts can be seen as a representation of an image or an ideal, one which she and Gatsby seem to share regarding wealth, glamour and self-presentation. 

The shirts themselves mean little. They are merely cloth. What they represent is quite meaningful, however, as Daisy and Gatsby both prize appearances and fantasy over substance and reality. 

This notion is borne out by the nature of their liaison, which consists of a series of conversations about how great things will be in the future, and also borne out by the fact that Daisy does not leave her husband. The affair between Daisy and Gatsby is, ultimately, simply a show. It is a play at a romance, an image of love. 

The shirts then are related to the idea that appearances are important to these two. It is the image that they respond to, not the substance of the thing(s). 

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