Dean has green eyes, freckles on his face and short-cropped hair that is dark blonde. He is 6'1"—ironically making him shorter than his younger brother Sam—and muscular. Dean is noted to be "handsome" or even "pretty" by other characters on multiple occasions.He usually wears a plaid shirt over a T-shirt, jeans, and boots, unless he has to wear a disguise in order to impersonate someone. Until Season 6, Dean often wore his father's leather jacket. He also used to wear a watch and a silver ring. As of Season 4, Dean has a hand-shaped burn scar on his left shoulder from where Castiel pulled him out of Hell. This mark has since disappeared from his body.For the first four seasons, Dean also wore an amulet around his neck that resembled the head of a bull made of brass, attached to a black cord. This amulet was given to him by Sam as a Christmas gift when they were children. Throughout the first half of Season 5, Castiel attempts to use this amulet to find God, as its claimed power is to burn hot in God's presence. When Castiel is unsuccessful, he declares the amulet "useless," and Dean throws it away.Dean mentions to Haley Collins in Season 1 that he doesn't wear shorts.Dean has recently received the Mark of Cain, manifesting just below his elbow. Since separating from Sam his appearance has become more scruffy and unshaven.Dean briefly possessed a pair of black eyes while he was a demon but they are gone now that he's human again.
Dean is shown to be by turns understanding, kind, funny, mischievous, and, in contrast to his younger brother, a little immature. At an early age, Dean was trained by his father, John Winchester, to hunt and kill creatures of the supernatural. However, unlike his brother Sam, he did not resent his father for having him "raised like a warrior". He seemed to prefer hunting the supernatural over any normal "apple pie" life, though it was revealed that when he was Sixteen, he did in fact desire (or at least hope for) a normal life: He just couldn't leave Sam. This however did not last long, as later on while still Sixteen, following a Werewolf hunt he realized just how unique his life was. However, by Season 7, following all that he has seen and done, Dean admits to Eliot Ness that he no longer wants to be a hunter and would give it up if he could.Dean is an avid fan of classic rock music. Many of his aliases have included the names of famous rock musicians. He is known to use crude humor, make sexual innuendos and indulge in pornography (especially for Busty Asian Beauties).Dean typically avoids emotional intimacy, preferring to engage with women only as sexual partners. However, he has had a few long term relationships over the years, with Cassie Robinson, pre-series, and Lisa Braeden, in Season 6. After the tragic events that led Dean to ask Castiel to make it as if Lisa and her son Ben had never met him, Dean seemed to give up on ever having a family other than his brother. After his break up with Lisa, Dean was reluctant to get back into his old routine of "New Town, New Girl". However, the one time he was shown to indulge in a one night stand in The Slice Girls he ended up fathering an Amazon that tried to kill him. He was reluctant to defend himself against his Amazonian daughter and Sam ended up making the kill. After these events he became even more reluctant to get in a physical relationship let alone an emotional one.Dean values his family's safety over anything else, even going so far as to kill a demon and its human host in order to save Sam's life, as well as sacrificing his very soul and suffering in hell to resuscitate his brother.Even though Dean keeps himself in excellent physical shape, he is known to have very bad eating habits. He is often shown enjoying greasy, fattening or otherwise unhealthy food, especially cheeseburgers and pie, and dismisses salads as "rabbit food".Dean is terrified of flying and claims that is the reason why he drives everywhere.Despite his working knowledge of the supernatural, Dean is skeptical with regard to the "good aspects of religion." However, he becomes somewhat more open-minded after meeting the angel Castiel.Dean has also shown on several occasions that he is a great fan of movies, particularly westerns, and was thrilled to be given a chance to go to the old west. He was also overjoyed when he met and was able to work with Eliot Ness, frequently referencing The Untouchables during the episode.Dean is typically ruthless and aggressive when he is hunting, a task which he approaches enthusiastically, making him the more merciless of the Winchester siblings. But in spite of that, he is capable of acknowledging whenever he's going too far, as seen with his interaction with Lenore and Gordon. Whereas Sam is at least willing to sympathize with what they hunt, provided that their motives can be counted as morally gray, Dean mostly sees the world as black and white. He passionately despises what he hunts, especially demons, and is prepared to kill without question more often than not, unlike his brother. This has caused him to develop a bigotry against most supernatural creatures and beings.He dislikes showing his emotions to monsters, and when facing beings like Abaddon or Azazel he acts threatening and determined. When facing the angels, even knowing what they could do to him, Dean is sarcastic, rude, and insulting. The only being he is openly afraid of is Death; on the rare occasions that they meet, Dean is nervous and cautious, and when Dean is angry or frustrated enough to talk back, he becomes visibly scared and backs off the moment Death appears annoyed.Despite these traits, Dean is very laid-back and well-disposed when not on the hunt, and he values the safety of his family and innocent civilians above all else, even his own life. Though on occasion he can be somewhat impulsive as well as arrogant, Dean is both extremely intelligent and competent. He is more likely to exhibit irrational behavior when his family is threatened.Underneath his seeming arrogance and self-righteousness, Dean shows many signs of self-loathing and insecurity. He always blames himself when things go seriously wrong, regardless of whether he's to blame or not. He constantly downplays himself and his achievements. He puts up with abuse from others, simply because he believes he deserves it. Despite being the better hunter, Dean admits he doesn't see himself as anything other than a "grunt". Likewise he constantly is willing to throw his life away, at least in part because he doesn't value it as worth much. He is constantly called out for feeling this way by Bobby and Sam. But regardless his feelings always return. These feelings can be traced back to his relationship with his father John, who at times treated him as a tool rather than as a son and who held him to unrealistic or unfair standards.Dean enjoys the uncomplicated things in life, such as good food and television. He almost constantly displays some level of humorous behavior, and frequently makes light of tense situations. He sometimes appears foolish due to this habit, but this seems to be merely his means of dealing with the stress of hunting.Dean shows on multiple occasions a soft spot for children. He is very good with them, able to talk to them with ease, and he is always very sympathetic; this most likely stems from the fact he practically raised Sam when he was a child. Dean's affection extends to nearly all children, particularly young ones, although he also cares about teenagers. Dean is more willing to put his life in danger for children than he is for nearly any others. Dean's affection even extends to monster children, and despite his ruthless approach to hunting he's usually unwilling to kill monster children unless he has a crucial need.After his extraction from Hell by Castiel, Dean begins to exhibit noticeable anxiety and experience chronic, abominable nightmares of his experience there. He also seems to have some form of flashback after seeing a collection of masks in the episode It's the Great Pumpkin, Sam Winchester, when blood is seen around eyes, such as Alistair's first appearance, when a statue's eyes bled. Initially, Dean denies remembering anything of his time in Hell, but eventually confesses to Sam that he remembers every detail. He rejects any discussion about it, either not wishing to burden his brother with his pain or not wanting to relive the details of the "indescribable things" he saw. He later reveals that he not only saw terrible things, but (in Hell time) was in Hell for around forty years. He confesses that he lasted thirty years without torturing other souls so as to escape the torment himself, but that he finally broke down and tortured for the last ten years. Dean's experience in Hell left a profound mark on him. He exhibits extreme grief and guilt, both for his own torment and for the fact that he eventually gave in and tormented others. Due to this, he believes he was unworthy of rescue. He has also explained to his brother that he wishes he couldn't feel anything, as the sorrow he feels is so overwhelming. He has become obsessed with saving people, often going without sleep in order to save as many as he can. In the episode Family Remains, however, Dean states it is not just the fact he tortured souls, but the fact he enjoyed it which causes his guilt and shame. Taking up the instruments of torture himself gave him the opportunity to put his pain on other unfortunate souls. It was this act, of a righteous man turning on others, that broke the first seal.Another side of Dean shown recently is his utter disgust at Sam for many of his dangerous or foolish actions, such as drinking demon blood, and having a sexual relationship with a demon, possibly because he is scared of Sam becoming a demon like the ones he saw in Hell. While he remains angry at Sam, he vows to save his brother and still loves him. Dean also realizes family isn't perfect and there will always be times when they hurt him. In the final episode of season 4 after the argument with Bobby when he was in the "safe house", he forgave his brother during the final few moments when Lucifer was rising.As of Season 5 Dean does not trust Sam, and feels as if he is holding himself back and putting the world in jeopardy just to keep Sam safe. He tells Sam that Lucifer will use the fact that they are family and have love for each other against them until he was sent to the future by Zachariah. Once there, he realized that he and Sam kept each other grounded, and when he got back, he immediately called his brother. They were a team again, even though it was difficult for Dean to trust his brother again, as Sam continued to lie to him.After his time in Hell, Dean slowly started to use alcohol as a crutch. He cut back on his drinking while he was living with the Braedons between Seasons 5 and 6 but after being kicked out of the Braedon Household after the events of Live Free or Twihard and You Can't Handle the Truth his long term depression worsened and he dove back into the bottle. In Season 7 both Bobby and Sam stated that his drinking was becoming a problem that could potentially cost him his life during a hunt.Following Bobby's death at the hands of Dick Roman, Dean developed a very strong, obsessive revenge streak in him and spent the entirety of Season 7 hunting Dick down to kill him. As part of Bobby's last wishes he tried to let go of his anger and vengeance, and while in the end he succeeded in killing Dick, it was as part of the job and not for vengeance. However, this caused to him be sent to Purgatory in the process, where he resided for a year (possibly much longer, as time moves differently between dimensions).The constant life-or-death situations Dean was forced into in Purgatory created an extreme change in him. While he was stuck there, he became emotionless and paranoid of the fear of getting attacked. He killed monsters of Purgatory with ease and was always fighting for his survival. When returned back to Earth, his new outlook on life was clear. He became hardened, emotionless, and at times ruthless; his humor and puns were nonexistent when hunting unlike in Season 7. That has changed with Castiel's return from Purgatory after which he started to show his lighthearted side again.Having a now haunted sense of self created in him during that year, he became firmer in his belief of hunting. He had personally seen all the monsters they hunted in Purgatory and in doing so, developed a strong sense of responsibility to the people they saved. Dean now believes that it is their duty to save people and quitting out of the hunting business is permanently out of the question. Despite becoming more ruthless, Dean has developed more faith in monsters managing to recover their humanity, as shown with him willing to let Kate go, presumably developed from his time with Benny. However following Castiel's return, Dean began to slowly return back to his previous more laid back personality.Following Kevin's death, and Gadreel taking complete control of Sam, Dean became desperate to save him. When Sam was freed, Dean's self loathing seems to have reached a new height: He claims he's poison, and that anyone near him dies.Since acquiring the Mark of Cain, Dean's personality began to alter, turning darker. He has since shown extreme levels of aggression and wrath, an example of this is when he fully attacked a good angel and putting an Angel Blade to her throat in Stairway To Heaven. As well as being openly more hostile, even towards his friends and brother. He's also got more distrusting and suspicious, and more hate-filled toward the supernatural.From what has been seen so far, Dean's transformation into a demon has darkened his personality. As his soul is twisted, he no longer empathizes for others, and only cares for his own needs and wants. He is so far from his former self, that at one point, he stalked Sam through the bunker and attempted to kill him with a hammer, missing only by inches. He also seems to like taking his time with his tasks. While stalking Sam, he talked in a taunting manner, as though he was enjoying himself. This is furthered by the fact that instead of an axe, he decides to use a hammer to break through a door and kill Sam, despite both tasks requiring much more force with a hammer than with an axe. Dean as a demon apparently cares about the natural order, something old Dean despised. He even considered himself, as a demon, a part of the natural order, and that it was all set up in this certain way.Sure enough, the transformation has turned Dean more selfish and arrogant, acting like a hedonist and only caring about himself, completely in opposition to his former personality. He has kept some familiar traits, such as a love of drinking, roadhouses and games such as pool, darts and foosball. Dean is now noticeably more brutal, happily beating people and demons beyond a reasonable point, with limited provocation. He is also colder, and while initially coming across down-to-earth and charismatic, he quickly turned cold and ruthless when others proved to be uncooperative, as shown by him outright shaming and humiliating Ann Marie for sleeping with him the moment she rejected his advances, not caring that he had left her near tears.Dean's transformation has also caused him to no longer care for Sam, shown by how he told Cole that he didn't care what he did to Sam, and even threatening Sam himself. He has also shown to no longer care about innocent people, willing to kill a cheating housewife just to sate the Mark's need for a kill and instead killing her husband, as well as calling his beloved Impala 'Just a car' and not bothering to tend to it's condition.