There’s nothing more overtly pompous than blatantly describing yourself as “preppy,” or acknowledging that you consider yourself to be a part of that culture. I’m pretty sure if Nantucket did a survey on personality attributes considered to be most important when living that lifestyle, number one on the list would be “understated.” Town & Country completely disregarded this when publishing the 40 Preppiest Nicknames Ever, and anyone that shared this article repping their own name officially became the biggest dickhead in anyone’s newsfeed.
Granted, if you did a “Preppy Name Generator,” my name would probably pop out as is at some point. My middle name is preppier than my first name, and the Roman numerals at the end only solidify my place in basic-white-boy history. But when it’s all said and done, and I name my son after myself (only with III at the end), you better believe I won’t be calling him Trey or Trip. That’s a recipe for him getting his turtleneck pulled over his face before getting a swirly in the middle school bathroom.
To the names.
For The Girls
If I were at a bar and a girl introduced herself as “Bettina” to me, I’d inadvertently spit beer in her face at the absurdity of it. What F. Scott Fitzgerald novel do Bettinas even come out of anyway?
Bitsy loves two things in life: her Lilly Pulitzer Dark ‘n Stormy Dress and her dad. I won’t fault her for either.
Madison (who was hands-down the least intelligent cast member ever) from last year’s Real World: Skeletons was nicknamed “Bunny” and it makes complete sense. When you think of a “Bunny,” you think of a blonde bimbo who hooks up with a dumb bro from Texas. Stereotypes are there for a reason: they’re true.
Every Cece in the world can thank Cece from New Girl for her taking this name up the ranks and making everyone default to “she’s probably hot” when they hear it.
Chasey had to have been the name of one of the little girls that Owen Wilson played with to impress Rachel McAdams in Wedding Crashers, right?
There are two types of Dedes in this world: your 50-something year old godmother and the little black kid from My Brother And Me on 1994 Nickelodeon.
I’ve never come across an Ellie that I wouldn’t. Ellie Goulding? Ellie from That Awkward Moment? Ellie Kemper from Unbreakable Kimmie Schmidt? Would. Would. Would.
Screams “high maintenance.” Anyone that names their kid “Gigi” is an asshole.
I know one Hilly and she’s engaged to a D1 quarterback. This, for obvious reasons, adds up.
My mom’s friend’s name is Izzy and when I was 12 she called me a “little shit” on the golf course because I got overly upset after a shot. Have yet to forgive her.
I’m betting on Jason Sudeikis calling Olivia Wilde “Liv” when they’re both separately working in their kitchen and he needs something. And because it’s entirely possible Jason Sudeikis is my estranged brother / Olivia Wilde is my future sister-in-law, they can do whatever they want.
“I don’t care how close you are. In the end, your friends are going to let you down. Family: they’re the only ones you can depend on.” – Tony Soprano
Drink of choice: white wine on ice in a pint glass, which is also the trademark summer drink of yours truly.
Not saying I wouldn’t.
Try saying this without sounding like Frasier Crane during the intermission of an opera. Didn’t work, did it?
No one has the name Peachy. Hey Town & Country, edit your articles better. Who do you think you are – me?
I met a British person named Pippa once, and I’m pretty sure she never once looked me in the eye when she talked to me. Whether that was her being rude, shy, or just plain British, she tarnished the name Pippa forever.
That being said, Pippa Middleton is attempting to clean this mess up by being the sneakiest Most Eligible Bachelorette on the face of the earth. If the Hot Bro Bracket had a female equivalent (sup, 2016?), you’d be hard-pressed to find a better number-one seed for the Etc. Region.
Can’t and won’t hate on Pollys. Once fell in love with one on a dance floor during a scorching rendition of “Werewolves In London” before Douchebag Pete made out with her in the back of a car 20 minutes later. The one that got away.
…is jealous of her sister’s marriage. #AlwaysABridesmaid #NeverABride
Tibby is a member at her local country club, but rather than having a golf membership, she simply has a “social” membership that involves the pool, dining room, tennis courts, and casual bar.
Yo Town & Country, how you gonna put Topsy on this list and not “Flopsy?”
For The Boys
Chip has a green blazer, cream pants with pleats, and great hair. And he looks awesome.
Finn is the dude who uses his parents money not to live lavishly in some generic midwest-or-east-coast American city. He uses it to travel in Patagonia or drive a refurbished Land Cruiser through Africa. But this is all before settling down and reluctantly taking a job in marketing in San Francisco.
Detroit muscle, baby. Detroit muscle.
“Gib” is the type of name you drunkenly draw out at a bar after not seeing your buddy for two years.
“Gibbbbbbbbbbbbbb!” And then you have Mount Gay-Sodas over it and make plans to visit each other this fall for a football weekend.
Can’t lie, Hays is kind of a Hot Bro name. May call my third-born son Hays because everyone knows my second-born son’s name will be Barritt (Bear for short).
Holtie played varsity hockey at Williams for 4 years and is built like a moose. His teammates describe him as a “workhorse,” without fail:
“Yeah, Holtie, ya know. He’s a great player. Gets to loose pucks, never gives up on a shift, always looking out for the team. He’s had the silkiest mitts in New England three years running and is always looking to go top titty. Can’t say enough about him.”
Actually, this is freshman-year Holtie:
Holtie also still isn’t over the Hartford Whalers moving to Carolina even though he was only 8 when it happened.
Kip has yet to come out of the closet even though everyone knows that Kip is clearly in the closet (not that there’s anything wrong with that, Kip. We just want what’s best for you.)
I cannot have an Ollie in my crew. I can’t even imagine what my friend Todd (whose name was grossly omitted from this list) would do if I told him, “Hey, mind if I bring my buddy Ollie along with us?”
Actually, I know exactly what he’d do. He’d say, “Yeah, man, stop by. But do not bring that doorknob Ollie around me.”
Pearse (or Pierce)
Two words: Pierce Bush.
Sebastian, or “Seb” for short, took his name way too far when he was studying abroad and now pretty much refuses to leave Provence unless it’s for a wedding for his boarding school buddy.
Topher used his parent’s allowance in college to buy really good weed and is now on the same career trajectory as Rubin from Road Trip who created a new strain of grass undetectable to drug tests.
The only Toppers I know are the vodka ones you ask for on your Lily at The Kentucky Oaks.
Trip works for a Manhattan-based venture capital firm that his dad started for him after his 5-year stint at Trinity, but everyone’s nice to him because they think he’ll be able to help them somewhere down the line.
Van. Doesn’t. Care. That. She. Has. A. Boyfriend.
Much like New Girl did for Cece, Webb (alternative spelling) Simpson changed the landscape for all the Webs in the world after he won the US Open and became a two-time member of the US Ryder Cup Team (albeit a shitty one).
I know like three people named Wells, and I honestly wouldn’t be surprised if any of them were in the above picture. Just a thoroughbred prepster name, through and through.
Alright, fuck it. Who am I kidding? I’d hang out with every single one of these dudes – Win, Topper, Kip, Finn, the whole lot of ’em. Except Ollie. Ollie is such a fuckin’ doorknob. .