What does "preppy" sound like? That's the question I set out to answer with this compilation. I had two basic guidelines in mind:

1. The music should be generally similar to Vampire Weekend (since anyone who knows anything about either Vampire Weekend or prep would probably agree that they're two peas in a pod).
2. The music shouldn't sound out of place if it were played in an American Eagle store. (Yes, I know the old-school preps out there will choke on their gin-and-tonics and protest that "American Eagle isn't really prep!" But prep rock? Yes, I would say it is.)

I wasn't really concerned with representing a wide variety of artists, so some of them get significantly more time than others (Vampire Weekend and Shout Out Louds, in particular). What I was most concerned with was capturing the right sound and mood. I also tried to ensure that songs flowed nicely into one another, which is why I decided to feature this basically as a CD-burnable playlist, and why I would recommend that you listen to the songs in order, at least the first time.

The zip file includes all 23 songs, plus cover art, and high-quality printable PDFs of CD case inserts (of which I'm rather proud, if I do say so myself). And here's the track list:

1. Peter Griffin - The Spirit of Massachusetts
2. Vampire Weekend - Mansard Roof
3. Shout Out Louds - Fall Hard
4. Canvas Kites - Vacation (Take You Away)
5. This Is Ivy League - The Richest Kids in Town
6. Shout Out Louds - Your Parents Living Room
7. Mystery Claws - Phony Checks
8. Ra Ra Riot - Massachusetts
9. Vampire Weekend - Oxford Comma
10. Surfer Blood - Take It Easy
11. Hungry Kids of Hungary - Wristwatch
12. Vampire Weekend - Cape Cod Kwassa Kwassa
13. Ra Ra Riot - Shadowcasting
14. Shout Out Louds - Normandie
15. Spoon - The Underdog
16. Vampire Weekend - Holiday
17. Shout Out Louds - Shut Your Eyes
18. Dr. Dog - Stranger
19. Two Door Cinema Club - Eat That Up, It's Good For You
20. Vampire Weekend - Walcott
21. Shout Out Louds - Impossible
22. Prep-Unit - Tea Partay (Director's Cut)
23. Peter Griffin & Company - The Spirit of Massachusetts (Reprise)

Download now! (175 MB ZIP file - click green Download button under "save file to... your computer")

I've been sick the last couple days, but I managed to catch The Kennedys on the History Channel last night. I am in love with this cardigan worn by Tom Wilkinson as Joe Kennedy Sr. Even the pockets have tipping!

This past Friday my wife and I visited the Salvation Army Thrift Store in the Kerr Village area of Oakville, a suburb of Toronto known for being full of rich people. I think I can fairly safely say that, at the least, people in Oakville must own really nice stuff, because what they get rid of is pretty amazing:

Each item in the above photo was $1.99, except for the shoes, which were $8.99. I don't often have good luck with clothes at thrift stores, but I can usually find at least one tie that's decent. But finding two that are so perfectly preppy is unprecedented. First we have the very nautical Chubb Marine Underwriters tie, which would look perfect with a blazer:

Silk face, polyester lining, 3 1/8" wide, made in USA.

And then of course we have the game-bird critter tie:

All silk, 3 1/2" wide, made in England.

I'm not completely certain what kind of bird it is, but going by this picture, I'm pretty sure it's a grouse.

But I think I'm probably most excited about the Sebago burgundy tassel loafers:

Leather upper, leather sole, made in USA.

I love tassel loafers, and these will go just perfectly with khakis, navy or grey dress pants - hell, even my white linen/cotton pants. Of course they need a little spit and polish, but there's nothing seriously wrong with them, so they'll clean up very nicely. They look a lot better even after just putting in shoe trees.

And the runner-up for Most Exiciting Item is definitely The Kennedys: Portrait of a Family by Richard Avedon. I actually gasped out loud when I pulled it off the shelf. It features never-before-seen family portraits of the Kennedys taken by Richard Avedon and donated to the Smithsonian before his (Avedon's) death.

Next weekend? The Oakville Value Village!

Although it's three years old, I just stumbled on this excellent photoessay from TIME Magazine on JFK's personal style. It's a slideshow of pictures narrated with commentary on what made Kennedy's style so unique and influential. And it occurred to me as I was looking at these pictures that JFK's style can be seen as a combination of two huge trends in men's fashion over the last 3-4 years: traditional Americana/prep, and the '60s revival brought about in large part by the TV series Mad Men.

Left, President John F. Kennedy; right, Mad Men's Don Draper.

Look at above picture—the entire JFK slideshow, in fact—and you'll see the building blocks of Don Draper's wardrobe: narrow lapels, narrow ties, white shirts with small-proportioned point collars. But also in those pictures, especially the more casual ones, you'll see the foundational elements of classic American sportswear: button-down shirts, polos, crew-neck sweaters, khakis, sneakers, Ray-Bans.

Left, JFK; right, a page from the J.Crew September 2010 men's catalogue.

These elements are as close to timeless as you can get. They're the basic staples of the American man's wardrobe. They may pass in and out of fashion, but they are never out of style. GQ even went so far as to compile a list of "10 Things That Will Never Go Out of Style," and, while I think that it's a little too early to make a judgment call on Timberlands, I don't seriously disagree with the rest of the items they list. (Ray-Ban Wayfarers have made a rather tragic hipster comeback lately, but hopefully they'll soon return to their roots.)
Now you may argue that it's facile to compare Kennedy to a J.Crew catalogue when J.Crew doubtlessly draws conscious and perpetual inspiration from Kennedy, but in a way that's exactly the point: you can't draw perpetually from Kennedy unless there's something timeless about his clothes. And these staple clothes are the ones you'll always be able to find in stores. You could do worse than to build a wardrobe around them.

As for Mr. Draper, it could be said that the '60s skinny-suit trend is really just an iteration of the skinny-suit trend that started with Hedi Slimane and Dior Homme in the early 2000s. Really, how long were D&G (and H&M, for that matter) doing narrow lapels before Mad Men came on the air? But the Mad Men look is a little bit different: the jackets are slightly less fitted, the closures somewhat higher. The Dior Homme look was more about leanness and length and androgyny; the Mad Men look is vintage '60s, when men were men, and even a refrigerator-shaped gentleman could get away with a slender tie and lapels. I'd caution anyone against embracing it too fervently, since the pendulum is bound to swing back the other way, but I personally have one grey pinstripe slim suit from H&M in my wardrobe, and it's great fun to Draper it up with a white French-cuff shirt and a skinny black tie every now and again. All you need to top it off is a pack of Luckies, two fingers of rye, and of course, the right gel. Smashing!

...or at least, smashed.