preppy

Courtney from Total Drama Island

Courtney isn’t what you probably think of when you imagine someone on a reality TV show. Voiced by Emilie-Claire Barlow for most of the show (Rochelle Wilson voiced Courtney in two episodes), it quickly becomes clear that Courtney is in it to win it and that she has big plans for the prize money. Unfortunately that leaves her little room for patience with other contestants. Especially Duncan. Or so she claims.

Courtney’s style is thankfully not as high maintenance as she is and it makes for a great closet cosplay. A grey sweater matches grey gladiator sandals which coordinate with green capris and a white button down shirt worn under the grey sweater and cuffed at the elbows. A brown bobbed wig – or your own brown bob – finish off the look.

Sherri “Cherry” Valance from The Outsiders

Sherri “Cherry” Valance (played by Diane Lane) is a character in the film The Outsiders, directed by Francis Ford Coppola.  Unlike Ponyboy and Two-Bit, who are Greasers, Cherry is an extremely popular girl and a member of the Socs, though she is much nicer than many of her peers.  Cherry has long, red hair and her clothing appeals to her social status, with clean lines and preppy colors.

Carlton Fresh Prince of Bel Air

Carlton Banks from Fresh Prince of Bel Air

In the Fresh Prince of Bel-Air, Carlton Banks (Alfonso Ribeiro) is Will Smith’s rational yet cocky cousin. In spite of his wealth, he has little success with women. Sometimes his selfish attitude can clash with Will’s more laidback approach, but he’s still his best friend. His style is preppy and conservative, and you can’t go wrong with a cardigan and sweater vest. And of course patterned pants, as per the 90s. Once you’ve assembled your costume, do the Carlton dance!

Blake from Wet Hot American Summer

Blake McCarthy (Josh Charles) is a Camp Tigerclaw counselor who’s dating Katie, a counselor at neighboring Camp Firewood. He starts spying on her though after he sees Andy hitting on her. He wears not just one or two popped polo collars but three, all of which are looking particularly popped.

Courtney from Wet Hot American Summer

Courtney (Kristen Wiig) is a counselor at Camp Tigerclaw who has the hots for Blake, and drops some serious innuendos with her uncomfortable application of lip balm. Despite the pearls and pink outfits, she can get down and dirty during a brawl – all she needs is an oyster fork.

Ben from Wet Hot American Summer

At Camp Firewood, Ben (Bradley Cooper) is theater co-counselors with Susie, who also happens to be his girlfriend. Ben’s a man with many talents. He’s a triple threat who’s able to act, sing, and dance, plus he can keep a party going with his skills as DJ Ski Mask. During the course of the summer, he learns from McKinley that he’s not just talented but he’s creative too.

Nancy Drew

Emma Roberts plays Nancy Drew, a teenage girl with a knack for sleuthing. She tries to fit in at high school, but realizes that she’s most at home wearing preppy clothes and investigating unsolved murder mysteries.

Rachel Berry

Rachel Berry, played by Lea Michele in Glee, is a driven yet neurotic high school glee club member, who’s single ambition is to perform on Broadway. She places gold star stickers after her signature to remind everyone that she’s a star.

Blaine Anderson

Blaine Anderson (Darren Criss) used to be the lead singer of the Dalton Academy Warblers but transferred to McKinley High School to be with his boyfriend Kurt. Though he may have shed his Dalton blazer, he sure hasn’t given up his preppy style.