At first glance, Dallas Winston, known to his friends as Dally, comes across as a tough guy. The first thing we learn about Dally is that he can sometimes be in a “dangerous mood.” He is tough, independent, and resilient, or, as Ponyboy puts it, he is “tougher, colder, meaner” than the other boys. Ponyboy also describes Dally as “bitter” due to the fact that the greasers can never really beat the Socs.

In chapter 2, we learn that dishonesty is another of Dally’s character traits. While he, Johnny, and Ponyboy are in the drugstore, he manages to slip “two packages of Kools under his jacket.” When Dally and the other boys arrive at the drive-in, the trio sneak in despite having the money to pay, because “Dally hated to do things the legal way.” Dally is rebellious and has a devil-may-care attitude. He is also prone to violence—arguably more so than the other greasers.

However, we learn later in the story that Dally is fiercely loyal to the other greasers, and it is Dally who lends a helping hand to Johnny and Ponyboy in the aftermath of Bob’s death.

Arguably the most telling quote about Dallas’s character comes in the aftermath of his death, when Ponyboy makes the comment that “Dallas Winston wanted to be dead and he always got what he wanted.” Right to the very end, Dallas refuses to be conventional or to do what society expects of him.

In S. E. Hinton's classic novel The Outsiders, Dallas Winston is a memorable character who is depicted as a hardened teenager with an extensive criminal history. Ponyboy describes Dally as "tougher, colder, meaner" than any member of the greasers and goes out of his way to avoid him early in the story. Dally is notorious for street fighting, stealing, and getting arrested. Similar to most members of the greasers, Dally comes from a broken home and considers the gang members his family. He is depicted as a volatile outcast and unpredictable miscreant. Dallas Winston is also portrayed as reckless, disrespectful, and violent. He takes pleasure in breaking the law and is proud of his criminal record.

Despite Dally's many negative qualities, he proves that he is a fiercely loyal, trustworthy friend, willing to sacrifice his well-being and freedom for others. Dally is also depicted as resourceful, intuitive, and savvy. He quickly comes up with a plan for Johnny and Ponyboy to skip town and saves Ponyboy's life when he tries to reenter the burning church. Although Dally has a tough exterior, he is portrayed as a compassionate, sensitive young man who deeply cares about Johnny and loses control when he passes away. Overall, Dally is a complex character who is a notorious criminal but trustworthy friend. By the end of the story, Ponyboy develops perspective and comes to appreciate Dally.

Dally can be violent and impulsive, but he genuinely cares about Ponyboy.

Towheaded and shifty-eyed, Dally was anything but handsome. Yet in his hard face there was character, pride, and a savage defiance of the world. (ch 4, p. 59)

Dallas is the older friend of Ponyboy and his brothers.  He is described as “tougher, colder, meaner” (ch 1, p. 11).  Dallas Winston is nicknamed Dally by those closest to him.  He has had a difficult life, spending “three years on the wild side in New York” and getting arrested by ten years old.  Physically, he is distinctive.  Both his looks and personality are described in animal metaphors.

He had an elfish face, with high cheekbones and a pointed chin, small, sharp animal teeth, and ears like a lynx. (ch 1, p. 10)

This description also hints at Dally’s unpredictability and roughness.  The reader gets the impression that Dally is not someone you want to mess with.  He is street-smart and independent, and he can handle himself.  He has had a difficult life, and it shows in his demeanor.

His eyes were blue, blazing ice, cold with a hatred of the whole world. (ch 1, p. 10)

As the story starts, Ponyboy is weary of Dallas.  He is aware that he “hated to do things the legal way” (ch 2, p. 20).  This makes him anxious around him.

I didn't like him, but he was smart and you had to respect him. (ch 1, p. 10)

Dally’s rough exterior demonstrates itself in his treatment of Cherry and her friend. He harasses them at the drive in.

He started out bad and got worse.  Dallas could talk awful dirty if he wanted to and I guess he wanted to then. (ch 2, p. 21)

Despite Dally’s difficult behavior, the boys turn to him when they are in trouble.  When Johnny accidentally kills a Soc in the park, he and Ponyboy know that Dally can help them.  Ponyboy is nervous about going to him, but he knows that Dally will know what to do.

He didn't bat an eye when Johnny told him what had happened, only grinned and said

"Good for you" when Johnny told how he had knifed the Soc. (ch 4, p. 59)

Dally tells the boys to hide in the country and lay low until he can get them.  He has experience running from the law.  Ponyboy describes Johnny’s obsession with Dally as “hero worship” (p. 76) and says that Dally is the one he likes the least.  When Dally helps to save Johnny from the burning church, Ponyboy worries that he will be annoyed that the papers make him out to be a hero.  Dally would not want to sound heroic.

When Dally tells Ponyboy he was glad he didn’t kill him trying to get him out of the fire, Ponyboy’s opinion of him changes slightly.  He decides Dally is not all bad.

Dally shows a softer side when Johnny dies.  Frustrated and grieving, he robs a grocery store and goes on the run.  When the cops find him, he raises a gun so that they shoot him.  He commits suicide by cop.

The character of Dally goes a long way to establishing one of the major themes of the book: you can't judge people by the way they look.  Dally seems tough and mean, and he is.  Yet under that rough exterior he also has a good heart.

Angry: Dallas Winston displays his anger throughout the novel in many ways. He is continually fighting and is antagonistic toward others. Dallas's anger manifests itself in his rebellious personality. Dally is feared by those around him because of his short temper and willingness to hurt people.

Rebellious: Dally fits the description of a rebellious teenager. He was arrested at the age of ten and has been committing crimes ever since. Ponyboy mentions that Dally has been arrested for numerous offenses and has lied, cheated, stole, and even jumped smaller kids. Dally even sneaks into the drive-in movies simply to break the rules. Unfortunately, Dally's rebellious nature ends up getting him killed by the police.

Misunderstood: Despite Dally's tough exterior, he is a sympathetic, caring individual, who is often misunderstood by his peers. Dally has a soft spot for Johnny and even risks his life saving Johnny from the church fire. Dally hides his emotions in order to be viewed as a tough, menacing Greaser. As the novel progresses, Pony changes his outlook towards Dally and realizes that he is a misunderstood teenager.

Loyal: Dally displays his loyalty by helping Ponyboy and Johnny escape to Windrixville. He gives his friends money, a gun, and advice on hiding from the authorities. Dally also runs into a burning church to save Johnny from the flames. His selfless actions reveal his loyalty throughout the novel.

Dallas Winston: one of the best examples of the troubled youth.  Dallas is a tough as nails, emotionally hardened young man.  He has been getting in trouble since he was young because he hates rules and he had little guidance.  He acts as if nothing bothers him, but really everything does.  He is angry to be treated as a "thug", but he doesn't know how else to act.  He is angry when people challenge him or discriminate against him, and acts out violently.  But despite all these negative characteristics, he has love for his friends.  He helps Ponyboy and Johnny immediately, giving them all he can.  He runs into the church to help, because his friends are in there.  He loves Johnny like a brother, because he recognizes and cherishes the vulnerable, kind side to Johnny.  It is Johnny's death that pushes Dally over the edge, causing him to seek out his own death.