Dipper's cap and costume are quite an iconic image that runs through many Gravity Falls series. You need to understand that such a set of clothes will definitely not be suitable for a business meeting, but at a youth party it will look just right.
A little history
Dipper's first choice of hat was at the end of the episode "Trapped Tourist" when Stan Pines gave Dipper and Mabel a free choice from the Mystery Shack gift shop. After losing his original hat in a battle with the dwarves, Dipper chooses a blue and white pine hat.
In some episodes the hat is damaged, but it is always fine the next time it appears. In the episode "Land Before Swine", it is revealed that Stan also has a blue and white trucker cap on his gift shop shelf.
When Dipper and Mabel leave Gravity Falls at the end of summer in Weirdmageddon 3: Take Back The Falls, Wendy takes the hat and gives her lumberjack hat to Dipper.She decides to keep the pine hat as a memento of him until he returns the following summer.
In the episodes "Tourist Trapped" and "Weirdmageddon 2: Escape From Reality", Dipper wears his old hat: a dark brown and army green trucker cap with a brown star on the front.
In the movie Gravity Falls: Journal 3, it is revealed that he considered his old cap lucky and wore it since the fifth grade. He also never washed his hat because Dipper thought it would ruin his luck.
When he fights off the dwarves in "Tourist Trap" by escaping from them in the Shack's golf cart, he loses his hat. She is grabbed by the gnome, who falls off the cart after Mabel knocks the gnome away from Dipper's face.
In the game “Gravity Falls: Lost Legends” it turns out that Shmebulok (a gnome) took the hat and added it to his collection.
The hat, along with Magazine 3, is one of the most recognizable items in and out of the series.
What does the suit mean for Dipper himself?
The main reason Dipper wears this hat (and his old one) is to hide his Ursa Major birthmark, which he is ashamed of.
The hat is sold on several websites and the official Disney store, although one of the officially licensed Disney hats does not match the hat from the series, as it is a darker shade of blue and has a mesh back instead of a closed one.
This dark hat matches the one Dipper wears in the unaired pilot and in some concept art.
Mabel in Dipper's hat
Besides Dipper, Mabel and Wendy are the only characters to wear this hat in the series.
In Lost Legends, one of the alternate Mabels in MAB-3L is a mixture of Dipper and Mabel known as Maebipper, who wears her own identical version of the hat.
The hat also appears in the Disney series Amphibian and The Owl House.
In the Amphibia episode "After the Rain", Dipper's hat is among the objects in the "dance of love-need".
In the premiere episode of The Owl House, "The Lying Witch and the Warden", a hat similar to the one Dipper wore can be seen among the items in Eda's store.a
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