Wall Street is back, both in the theaters and in style.  From Indochino’s swanky new collection to the continued evolution of Ralph Lauren’s suiting wardrobe, city elegance is looking strong this fall.

OTC will be reviewing this new urban elegance and it honored to be working on a sartorial review of the new ‘Wall Street’ with Gordon Gekko’s original clothier, Alan Flusser.

Jack A. Mallon (#26) and his dad’s patched tweed blazer, ancient history class, squash racket and professorially demeanor added up to a winning combination.  I cannot tell you how hard it was to select a story that best reflected what being “preppy” is really all about and also told us all a little bit about the writer.  From seersucker at the Kennedy Center to matching Gold Cup outfits, prep schools to winning the right to not wear socks with loafers at the office, every one was a great read.

I will always laugh at the Georgetown bow tie “you’re-stealing-my-thunder” incident as well as the touching reminiscence of watching Sargent Shriver and his grandson in church, dapper and gentlemanly even in mourning for his late wife.

Other great lines include a friend noting that the “Dress code at Yale is apparently Andy Bernard style”; “Yep, my initials are BMOC”; and Andrew Y’s entire story of his big prep moment running into the realty that is old school prep plainness.

Thanks again to all who offered up their stories and please be assured that I read and re-read every one.  Each of you touched on the many aspects that mark the genuine nature of preppy culture.  From deprecating self awareness to duct-taped boat shoes, every one is it’s own cultural observation.

Here is the winning entry:

I’m a second year history student at the University of Guelph and last week, seeing as it was the first week of classes, I wanted to make a good impression. Dawning my father’s tweed blazer from his days at Guelph with the University crest and elbow patches, as well as khakis, a blue oxford, and a rep tie I set off for campus, bringing my squash racquet with me for a game later that day.

Upon reaching my Ancient History class about ten minutes late I strolled in, hoping not to interrupt my professor. As fate would have it I had been taught Latin by the professor several times, and when he saw me, halted his lecture and greeted me in Latin and started telling me how squash was his favorite sport and that he’d like to play me sometime. Glad to have avoided making a bad impression with my tardiness I took a seat for the remainder of the lecture. After class as I was walking down the hall I was approached by three or four students asking me a multitude of questions about the course.

It turned out that my friendliness with the professor and my overall appearance had led them to believe that I was the assistant professor. I played along and answered as many questions as possible. People can say what they wish about preppy attire, but for me it is the embodiment of dressing for success.

It’s a great town that keeps getting better.  One of the best parts of the visit was our meet-up at the original Harpoon Brewery.  Harpoon IPA is perhaps one of my all-time favorite beers and is, for better or worse, inextricably tied to many of my college memories. Thanks to Corey and the tasting room team for making our experience such a blast.

Founded by to Harvard grads, Harpoon was originally called the Massachusetts Bay Brewing Company.  Figuring that those are a lot of words to fit on a beer label, they came up with “Harpoon.”  Classic marketing: one word, two syllables, simple but iconic imagery and most importantly, a very good product.

We also were able to have one of our dinners up in the North End and spend an evening walking all over this great city.  A note of thanks to @BostonMo for some great restaurant suggestions.

I happened to be staying in the newly renovated South Boston Waterfront area, an easy stroll to Rowes Wharf and Quincey Market.  There are so may options when it comes to selecting your Boston base camp, but if you want to be in the middle of the action, take a look at Copley Square.  Bordered by the iconic Boston Public Library, Prudential and John Hancock towers, outstanding shopping and a plethora of restaurants, this part of town is a great place to plant your flag.

At $398.00 they are by no means cheap, but this being the world of Ralph Lauren, you also get some outstanding packaging,  a neat booklet and coordinating repp necktie.  The actual denim is manufactured by Cone Denim of Greenville, North Carolina, on 100 year-old shuttle looms.  It takes longer to make, uses more cotton than traditionally manufactured mass market denim and costs a whole lot more.

If you want them, don’t hesitate because Rugby only made 100 pair.

Ignatious was kind enough to send me a lovely shirt to test out and I’m darn glad he did.  It’s of course very well made of a luxuriously dense and fluid but lightweight cotton.  It’s also unique, as are all IJ shirts, due to its collar.  Joseph constructs only soft dress shirt collars, meaning there is no stiffness at all around your neck.

This is an expensive and rather complex process but it makes for a genuinely custom and unique fit, unlike any other dress shirt I own.  Overall, the shape is decidedly fitted but not overly slim or binding.  The sleeves are a tad too long on me and I plan to have them shortened.  He also makes fully custom shirts, but, as we are on two separate continents, I opted for a ready-made model so by no means is perfection expected.

Nonetheless, it is a virtually flawless and incredibly comfortable shirt.  It’s also a very sharp shirt, so much so that I wore it to the BeSpeak launch party over the summer.  While at the Custom Shop earlier in the day, the BeSpeak team sat around suggesting ties for my shirt and along the way it was immortalized in my BeSpeak virtual closet.

Now, as you can probably can see in these photos, I chose not to iron the shirt before snapping a few images.  While of course pressed and formal when I head out to the office, today I wanted to highlight the detail, construction and design of this shirt.  No better way to do that than by taking a look at it in its delightfully rumpled state.

Notice the obvious softness of the collar and collar band, the precise stitching, the fabric’s thick but soft hand.  You can also see the exacting matching of pattern and the signature shaping of the shirt, to better fit the wearer.

Clearly, this is  a great shirt.  But more than that, it’s made by a man dedicated to the art and science of shirt making; shirts and only shirts.  The love shows.

Take a few minutes and fill out an entry form at the link below for a chance to win 5 Tucker Blair belts, 5 Bonobos pairs of pants, and 5 Bonobos polo shirts (Valued at $1,500)!

Bonobos pants are legendary for their remarkable fit and comfort and Tucker Blair has quickly established itself as a new leading preppy lifestyle brand – so much so that their outstanding needlepoint belts are highlighted throughout the upcoming True Prep.

Enter Now: http://wildfireapp.com/website/6/contests/48987

I was genuinely ambivalent about this book.  How you could do a TOPH “Part II?”  so, my inclination was to sit back and see if lightning could again be bottled (in a madras bottle, of course, sitting next to a nice G&T).  My verdict?  Yep, Lisa Birnbach did it.

It’s a fun book that picks up right where the original left off.  She and co-author Chip Kidd happily point out that it’s been 30 years since TOPH first hit the shelves and a lot has changed.  From my black-and-white photocopied pages, I see the familiar lifestyle vignettes updated to reflect the Blackberry toting preps of today and read about the democratization of prep schools.

I’m also happy to see mentioned the importance of “modern” prep brands like J. Crew and Ralph Lauren alongside stalwarts J. Press, Brooks Brothers and L.L. Bean.  In fact L.L. Bean Signature, the newest ‘vintage’ market brand gets brief, favorable nod.

Equally refreshing is the focus on upstarts and small preppy labels that may someday be at retail’s forefront.  So to that end, OTC gives a big hand to Tucker Blair and its founder Taylor Llewellyn.  His needlepoint belts are all over this book and they have a nice write-up on how he started the company.  Very Vineyard Vines (Shep and Ian are also profiled).

What I also like is that I can just open the book to any page and start reading.  That’s always a good sign and something I love about TOPH too.  All in all, I can’t wait to see the finished product.  Cheers.