One Tree Hill: Peyton's 5 Best (& 5 Worst) Outfits | ScreenRant
For better or worse, the girls of One Tree Hill influenced an entire generation of television viewers, and girls in particular. Whether someone was more of a fan of Haley, Peyton, or Brooke, it's impossible to watch the series without attaching one's self to one of these characters.
Peyton Sawyer (Hilarie Burton) was always the series' resident brooder, an artistic girl with a tragic history who nevertheless saw the best in people and did whatever it took to make people happy. She changed a lot over the course of her six season run on the series, both in terms of her character, and her fashion choices. This list is taking a look back at the best and worst fashion choices she's ever made.
10 Best: Season 5, Episode 8
While the fifth season found Peyton at a point of change in her life, it also featured her in some of her best outfits in the entire series. The eighth episode of the season finds Peyton undergoing significant emotional turmoil, as her ex-boyfriend Lucas becomes engaged to his new girlfriend.
But she manages to overcome it all with grace and style, including in this particular mid 2000s outfit which included a light brown sleeveless top with pockets, a gold pendant necklace, and skinny jeans.
9 Worst: Season 1, Episode 21
The early days of One Tree Hill feature many a fashion miss, and poor Peyton had plenty of them in the earliest seasons. Her wiry hair is often a complete mess, and a complete miss for that reason, too.
Pair it with a very dated choker necklace, an unflattering purple layered tank top, and her typical denim jeans, and this first season outfit isn't just one of the worst of them, it's also one of the laziest, too.
8 Best: Season 6, Episode 1
When Lucas and Peyton steal away together at the start of the sixth season, they do so with the intention of getting married in Vegas, but with very little preparation for doing so.
But even so, Peyton manages to turn in one of her most effortlessly beautiful looks. Although the wedding doesn't come to be, Peyton is the perfect picture of a bride in a simple, short white sundress and with her newly straightened hair elegantly styled.
7 Worst: Season 4, Episode 17
After missing out on Tree Hill High's prom due to the attack of Psycho Derek (only one of the series' many stalkers), Peyton and the gang attend prom in a nearby small town, Honey Grove.
The boys and girls hit a vintage shop to try and find outfits. But Peyton's is by far the worst of them, featuring an unflatteringly cut light blue gown that hangs off of her like a sack, and an over-sized fur shawl that only further highlights her bony frame.
6 Best: Season 6, Episode 8
It's a shame that Peyton leaves One Tree Hill after its sixth season for many reasons. But one of the biggest reasons is unarguably the fact that she absolutely comes into her style stride in the series' sixth season.
Her hair has never looked better, and she's never been happier and more open, which is reflected in her colorful and feminine wardrobe. In the eighth episode of the sixth season, Peyton wears this stunning, simple purple cocktail dress and pairs it with an equally gorgeous pair of dangling earrings.
5 Worst: Season 3, Episode 1
One Tree Hill doesn't dabble in flashbacks very often, but when it does, the series - and its fashion - often suffer as a result. In the third season premiere episode, the series inexplicably flashes back to the second season finale, as if the episode hadn't just occurred.
In doing so, it's forced to account for changes in Hilarie Burton's hair, and it saddles poor Peyton with a mop-like wig and an unflattering tracksuit outfit that looks more akin to something one of Tree Hill's middle aged moms would wear.
4 Best: Season 5, Episode 9
Tree Hill High's library is known for being the setting of various dramatic events, but it's also the place where Peyton Sawyer wears one of her best outfits of all time.
When the Tree Hill girls are trapped inside the library in the fifth season, Peyton stands out as the clear fashion winner, sporting a low cut tank top, a vest, skinny fitting high wasited jeans, a layered necklace, and boots. Peyton may not be on her best behavior, or be in her best emotional state, but her style is absolutely on point.
3 Worst: Season 5, Episode 4
Simply put, there's nothing about this fifth season look that works. The early days of season five are especially hard for Peyton's style, whether in her misguided dark-highlighted mop of hair, or in her too grungy and gaudy fashion choices.
In the fourth episode of the season, Peyton attends the opening of Tree Hill's Clothes Over Bros store wearing a short, sleeveless, olive green, shiny dress with a cut so plunging, and so harsh, that it once again calls attention to Peyton's bony frame in unflattering ways.
2 Best: Season 4, Episode 8
It's rare that a series like One Tree Hill, which is so defined by the era of the early to mid 2000s, is able to produce a look that could be accurately described as timeless. But in the fourth season, Peyton manages to produce one of the series' only truly timeless looks.
When she attends the Tree Hill Ravens banquet with her half brother, Derek, Peyton does so wearing an absolutely gorgeous green dress, featuring a soft ribbon at the front, and a simple diamond necklace. It's one of the softer looks fans see Peyton in during the series' earlier seasons, and it's still absolutely stunning after all these years.
1 Worst: Season 5, Episode 2
The list has already established that One Tree Hill doesn't exactly have the best of track records when it comes to styling their characters in flashback scenarios. But none of them are as bad, and as downright unflattering, as this blink-and-miss it flashback at the start of the fifth season.
When Peyton attends Lucas's book signing in the past, she does so in a horribly unflattering and sparse pink dress, and she looks completely disheveled from head to toe, especially in the case of her messy highlighted flashback hair.