Guys Who Wear Vineyard Vines

John LeFevre
3 min readAug 26, 2019


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
  • Hate affirmative action but love nepotism
  • 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 old 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
  • Cheat at golf, and on their partners

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.

I also wrote about my relatively recent discovery of Mizzen & Main shirts. Most of my shirts come from Savile Row or Taipan Pan Row (my tailor in Hong Kong), so I have high expectations of my dress shirts.

But at the price point, Mizzen are now, by far, the best shirts I own. They are slimming and fit just as well as my custom shirts. The material is high quality and stretchy, so they are as comfortable as a t-shirt. They repel moisture so there are no sweat stains. And best of all, they are low maintenance — wrinkle-free and machine washable.

After I wrote that, they were kind enough to reach out and send me a box of samples from their new fall line, which I can’t recommend highly enough.

So I wanted to thank them by articulating what I think about Vineyard Vines, and what I know about the guys who wear them.

We’re now on Instagram. Follow here.

John LeFevre is the creator of @GSElevator, the founder of a fashion line, a podcast host, and the author of the New York Times bestselling book, Straight To Hell: True Tales of Deviance, Debauchery, And Billion-Dollar Deals, currently in development as a major motion picture.



John LeFevre

Signed contracts with Goldman Sachs and Simon & Schuster, and paid lawyers more than I made. Author of STRAIGHT TO HELL (not about @gselevator or Goldman Sachs)