Monthly Archives: February 2012

And the celebrity prep school grad of the week is…

…Ben Stiller of the Calhoun School in NYC. Calhoun is a K-12 school in Manhattan, and is known as a progressive school.

Stiller grew up with famous showbiz parents. Many people know his parents as Frank and Estelle Costanza from “Seinfeld.” Stiller graduated from Calhoun in 1983 and went to UCLA and studied acting before dropping out. You can’t argue with his decision, as he is worth about $120 million.

I could not decide which was the best Ben Stiller clip, so here is a montage of some of his funniest stuff. Enjoy!

As Derek Zoolander

Getting mad at Larry David

My Milkshake from “Dodgeball”

Pre-Prom scene from “There’s Something About Mary”

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Filed under Film & TV, Prep School Life

Signal Flag Leather Tab Belt – Crimson Red by Anchored Style

PRE-ORDER Yours today!  Shipping mid-March

  •  Made in Maine
  •  Exclusive ribbons stitched onto 100% 1 3/8″ cotton webbing
  • Tabs are fully stitched and cut from full grain leather and embossed with  logo
  • Buckles are solid brass in Old English brass finish
  • Sizes: 34-38 stocked (other sizes available upon request, each one is made to order).

        *order belts 2 inches larger than your pant size

I seriously can’t wait for better weather! Spring is defrosting the frozen hull of the SS Swag Surfer and if you’re as nautically prep as me, you better pre-order one of these Signal Flag Belts. Weather you need to hold up your all purpose shorts while relaxing on your boat, or a nautical accessory to match a tie, this belt is a must have for anyone’s wardrobe.

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Filed under Fashion, Swag for the gents, Swag for the ladies

Phillips Andover grad tallies his first goal for Crimson


Will Walker (Phillips Andover ’11) has certainly made his mark for the 15th ranked Harvard Crimson lax team over the weekend. The freshman attackman scored his first goal in his first game. Harvard went on to defeat UVM 11-4. Will’s brother Jack (Phillips Andover ’09) also had a goal.

***Note: in the video it says Will is committed to Duke. During his senior year, Will de-committed and then committed to Harvard***

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Filed under College, Lacrosse, Prep School Life

Get up for Gingham

Like it or not, Gingham is the next big hit in the prep style world. Gingham is a plaid-woven medium-weight cotton fabric. Perfect for warm spring afternoons and walking from class to class, you can’t go wrong  rocking a Gingham shirt with linen khakis, jeans, or  pleated shorts.

Check out Southern Tide’s take on the Gingham trend with their sport shirts and seersucker shorts.

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Filed under Fashion, Swag for the gents

Two Nobles athletes making the news

Noble & Greenough junior forward Chris Calnan has committed to play hockey for Jerry York and the Boston College Eagles starting in 2013. Calnan will join a strong Boston College team that has dominated Hockey East in the past decade, as rival Boston University has slipped.

Oliver White of Noble & Greenough School was selected as the 2011-12 Gatorade Massachusetts Boys Soccer Player of the Year. White is the second Gatorade Massachusetts Boys Soccer Player of the Year to be chosen from Noble & Greenough School.

The 5-foot-11, 165-pound senior forward scored 15 goals and passed for six assists this past season, leading the Bulldogs (13-3-1) to the New England Prep School Athletic Council Class A tournament quarterfinals. White is a two-time Independent School League Offensive Player of the Year. He concluded his prep soccer career with 41 goals and 16 assists.

White will be taking his soccer skills on the road to Harvard next fall.

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Filed under College, Ice hockey, Prep School Life, Soccer, Sports

And the celebrity prep school grad(s) of the week are…

Matt Damon and Edward Norton in “Rounders.” 

Yes, I know that neither of them really went to prep school, but in the movie, they said that they met at Dwight-Englewood Prep, which is a real prep school in NJ. Damon’s father cut the grass and Norton’s father was the drunk janitor. It is a stretch, but hey, this is a great poker scene with Teddy KGB.

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Filed under Film & TV, Prep School Life

Brewster knocks out Tilton in epic prep school hoops matchup

Two of the very, very best prep school basketball teams in the country met for battle in…New Hampshire??? Yes, that’s right. 

Brewster Academy and Tilton School did battle yesterday, and Brewster prevailed 60-56. Lots of future D-1 basketball talent on display for the 1,500+ fans who packed the house.

Here is more video from an earlier Brewster/Tilton game this season that ended in OT.


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Filed under Basketball, Prep School Life, Sports

Saluting our prep school Presidents on President’s Day

With everyone kicking back and enjoying a day off on President’s Day, I figured that we should recognize those men who graduated from some of our country’s finest prep schools.

Franklin Roosevelt on the Groton Football Team

First up to the plate is Franklin D. Roosevelt. I did some research, and it seems like FDR is the first true prep school grad to win the high office. His cousin Teddy Roosevelt was home schooled. FDR went to Groton, and as much as we sometimes hate on Groton, I have some friends there and you can’t deny its a great school. 

Check out FDR in his Groton JV football t-neck. Classic.


JFK is swag surfing

Following FDR was John F. Kennedy. We have already written about JFK being so prep. He went to Choate before it became Choate Rosemary Hall and then went to Harvard.  Just check out the photo above. JFK had so much coastal swag going on that it was ridiculous.

George H.W. Bush as a student at Phillips Academy in Andover, Massachusetts

The next President up was George H.W. Bush, who attended Phillips Andover, ’42. Bush was a legend at Andover, and went to Yale to play some baseball AFTER serving in the Navy in WWII. Despite his wealth and connections, Bush chose to serve his country before going on to college. He and his family are well liked in Kennebunkport.

George W. Bush at Andover

Last up is George W. Bush, who also attended Andover. Bush followed in his father’s footsteps in many ways, although he did not excel as an athlete as his father did. Like his father, “W” went to Yale and then got his MBA from Harvard. Even though he has solid east coast prep cred, W really has more cowboy swag than anything else.

So, in case you are keeping score, it’s Groton: 1, Choate: 1 and Andover: 2. If Mitt Romney becomes president, Belmont Hill gets 1/2 a point because Romney sent all his boys there.


Filed under Politics, Prep School Life

Why we love prep girls part II

I’m not trying to one up you dude! I know that The Boss posted this clip last summer, but this is so classic. It should be a follow up to the other prep school girl video from tonight. 

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Filed under College, Music, Prep School Life

johnnie-O releases new spring polos

Yes, we are technically in winter, but here in New England, we have yet to see any real snow. We are inching closer and closer to spring, and it’s time to think about updating your spring wardrobe. Your old polo shirts with stains of unknown origin from some random end of the summer party just aren’t going to cut it. That is why you should be looking at johnnie-O’s new polos HERE:

johnnie-O is one of my favorite clothing companies, but they are not well know here on the east coast. Let’s change that. Check out their swag and pick up a shirt or two today. I would post a picture of Chris O’Donnell wearing a johnnie-O polo at the Pebble Beach Celebrity Pro-Am, but I can’t find a non-copywrited photo. So, here is the next best thing, a picture of Jason Sudekis rocking a solid polo (he’s on the right–not the chubby Norwegian guy).


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Filed under Prep School Life, Swag for the gents