Guys who wear Vineyard Vines
A Choate alumnus who spent a decade in finance on the men in the pink whale shirts: 35 things guys who wear Vineyard Vines do.
By Beau Brummell, house column · October 31, 2026 · 2 min read
I went to Choate and was shopping at Vineyard Vines in the late 90s when it was a single store in Edgartown. Then, I spent more than a decade working in finance. So I'm an expert on the subject.
Let me tell you about guys who wear Vineyard Vines. They:
- Boast about high school sports accomplishments
- Kiss their dogs on the lips but their kids on the forehead
- Wear flip flops in Manhattan, and wear boat shoes in a landlocked state
- Hate affirmative action but love nepotism
- Still tell fraternity stories
- Leave bathroom stalls with 3 layers of toilet paper on the seat
- Bro-hug other guys they've met once
- Haze interns unnecessarily
- Love Will Ferrell movies
- Give themselves nicknames. "People call me Two-two; it was my Lacrosse number."
- Bribe college admissions offices
- Drink White Claw
- Leave prep school stickers on their Wagoneers
- Mime golf swings in the office
- Punctuate thoughts with "it is what it is"
- Dress like dicks at weddings
- Get their talking points from Tucker Carlson and Ben Shapiro
- Repeat the same stories at parties
- Make fun of fat people at the gym
- Give unsolicited advice, even to people who are more accomplished
- Sign work emails with "Cheers"
- Wear statement socks
- Live vicariously through a pro sports team
- Refer to the bathroom as "the head"
- Insult their friends in public to impress a girl
- Call their dad "my old man" and their wife "the boss"
- Have a Patagonia vest for winter and a Patagonia vest for summer
- Order a "Tito's soda" and hold eye contact like it's a power move
- Say "let's circle back" at a barbecue
- Own a boat named after a pun
- Introduce themselves with their college and graduation year
- Tip 15% and give a TED talk on it
- Name their Labrador after a bourbon
- Have a LinkedIn headline with "Dad. Husband. Builder."
- Cheat:
at golf - monthly
on their taxes - annually
on their wives - as often as they can
This article was inspired by something I wrote a couple of weeks ago, listing a few things I like (books, travel, fashion, games) this summer, and a few things that I don't like (Peloton, AirPods, White Claw, Lululemon shorts). And of course, Vineyard Vines.
The pick: Dressing the Man, by Alan Flusser. The classic guide to proportion, color and fit, for the man who wants to dress like a grown-up.
The Vineyard Vines guy: common questions
What is the Vineyard Vines guy stereotype?
In The Graze's list: a man who boasts about high school sports, gives himself a nickname, drinks White Claw, wears statement socks, mimes golf swings in the office and signs work emails with "Cheers". It is a portrait of a type, not of everyone who owns the clothes.
Who founded Vineyard Vines?
Brothers Shep and Ian Murray started the company in 1998, selling neckties on Martha's Vineyard from a backpack, their boat or their Jeep. Their first store opened in Edgartown, followed by Greenwich, Connecticut.
Why is Vineyard Vines associated with finance and prep school?
The brand grew from Martha's Vineyard and Greenwich, and its polos, quarter-zips and fleece vests became a uniform at Northeastern prep schools, colleges and Wall Street firms.
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