Celebrating the Preppy Lifestyle and it's sensibilities


Ahhhh yes!  Nothing says good times like sailing.  This is a new category that I've felt compelled to add.  It will be all about sailing and boats.  Since I've become a neophyte sailing enthusiast, I'm thinking how appropriate, as sailing and the prep lifestyle go hand in hand.
Though I'm personally partial to boats made of wood and not fiberglass, I must say I've always been drawn to the West Wight Potter.  This is the kind of boat that's not too big or too small.  You could hitch it up to even a compact car and be on your way.  And for the price, (potters start at 18,000.00 brand spanking new for say a potter 19 or as low as 4,000.00) you can't beat that.  Ideal as a weekend yacht, it's just right for say couples who just want to get out and enjoy a good sail.
The first West Wight Potter 14 was designed and built in 1960 by Stanley Smith of the Isle of Wight in the United Kingdom for a planned transatlantic crossing. Smith and his brother had previously made a crossing in a larger vessel and Stanley intended his design for a personal, single-handed attempt. As the story goes, the upcoming sea trial created such demand for Smith's new design that he gave up on his transatlantic plans and became a boat builder, eventually producing more than 150 copies of his little yacht. Smith did eventually sail one of his designs from the Isle of Wight to Sweden but he never did make his planned Atlantic crossing.

Smith's West Wight Potters were built of plywood and, in 1966, Herb Stewart of Inglewood, Calif., bought one, used it to make molds for a fiberglass model, and began HMS Marine, Inc., to build and market the West Wight Potter in the United States.


Here is a cool site where you can get used Potters


Before Martha's Vineyard became a tourist destination and one of the favorite places to vacation for preppies. Before the lighthouses of Cape Cod beckoned us like sirens of yore. Before Nantucket touched our hearts with it's quaint and quiet charms there was Bermuda.
Bermuda which is owned and under British rule was popular with the old WASP and preppies in the forties.
Remember, the Bermuda short was started here. Some would even argue that the famous Nantucket Reds called Breton red was actually started here.
I'm currently writing the draft to this post right here in Kings Wharf Bermuda. I will publish it when I get home. This is actually the wife and my second time here. The first time which was last year was in the historic St. George. It boasts the oldest Anglican Church outside of Europe, St. Peters also known as the unfinished church. We decided to take another cruise this year after we fell in love with Bermuda last year. Perhaps we can retire here someday. Interesting enough the average home in Bermuda is 1.4 million, not to mention that you have to rent before you buy for a solid year an amount that is even more than a two bedroom apartment in Manhattan. So we'll see about retirement.
Right now we're right across from The Commissioners House

This place is actually a British Fort that's also known as the Maritime Museum.

So like I've mentioned earlier, the wife and I decided on taking the cruise out of Boston. Let me tell you that it was an ordeal. We thought hey a nice road trip to up the coast through the southern New England States would do us good before the cruise. Wind in your hair, nice scenery, singing along with the radio and a chance to get closer, who could ask for more? Right, let's make a go it.
First off my wife decides on the day we were to leave for Boston (a work day) to get up and exercise. Now mind you, we reside near Annapolis Maryland and traffic can be pretty bad. We ended up leaving close to 11 o'clock. To start things off the GPS went screwy, directing us to go somewhere near Indianapolis. I fix that and 5 hours later we hit New York City Rush Hour. This set our time back quite a bit to say the least. To make matters worst, the stat of Connecticut decides to do a little construction at 7 pm. shutting all lanes down to one.
To make a long story short, the trip which should have taken us 9 hours tops ended up taking 12. Boston found us beaten, tired and begging for mercy.
Luckily the cruise was the next day and embarkation was starting at 1 o'clock.
The ship is called The Norwegian Spirit and she was huge. We really love this cruise line because they have freestyle cruising.  This means that you're free to eat, play or do whatever with no set times for anything.  We set sail at around 4 and to be honest I was exhausted. I took a nap and pondered all the exciting things to come.
Let me tell you if you're not aware. The Atlantic Ocean particularly around Boston are rough. Our cabin was FORWARD and we felt every wave. Now I pride myself having sea legs but that went right out of the window. My first day was filled with nausea and ginger ale.
Take my advice, if you ever plan on taking a cruise pleeeeeease demand a cabin between the center and AFT.
All in all I would still recommend cruising. It's a nice way to visit ports and just have a good time.
I shan't bore you further. Enjoy the photos and if you ever get a chance to see Bermuda by all means go. It's wonderful.
Oh and if you ever stay in Boston, you have to stay at the Seaport Hotel.  They're top notch.  Here's the link 


This was our tour guides Nigel and Karla  for an excursion we took.  They were a lot of fun.

- Posted by O. Cavanaugh Jr.



Just when you thought it was safe to come out of your historically, maple and oaked lined neighborhood for a quick game of tennis at the club. Heeeeere comes Lisa Birnbach. That lovable prep who thirty years prior gave America it's first real insiders look at the life of preps. We all know it. The Official Preppy Handbook was a bestseller in the eighties. Well she's back with a new book called True Prep, with Chip Kidd. It's another tongue and cheek look at the life of Preps now. It's release date is September 7, 2010. Also available in E book format. I hope that all 256 pages are as funny as the first book.
Here is what the NY Times says

Here is a quick video about True Prep. I think all in all it should be a fun read. Tell me what you think.


Well finally spring is here and you know what that means.  It's time to put away the pea coat, scarves and foul weather gear.  I wanted to do a post just for women preppy clothing.  Men will be next.  Preppy spring essentials are exciting this year.  So let's jump right in shall we?

Nothing says spring like a cool polo shirt, yes?
These three polo's are from the Vineyard Vines collection.  The one on top is the classic polo.  The pink one is the sleeveless pique polo.  The next one is a polo dress.  They all come in different colors and like all of Vineyard Vines Clothing, they are very durable and adorable.

Here is more from Vineyard Vines.  We have the Out to Sea Sundress, the Sailor Twill Skirt, the Seersucker Classic Skirt and despite it's name the Wale Tail Shorts.  Two of my favorites are the Seaton Dress and the Schooner Dress.  Last but not least, for those chilly mornings, the Sea Island Cardigan.  They're tres preppy.

You know a lovely alternative to a ribbon belt is to opt for a scarf or tie.  This example is from Vineyard Vines.
LL Bean's new line called Signature has some nice ensembles.  I will discuss LL Bean Signature Line in a later post.  Here are in my opinion some must haves:
At the top we have the Belted Twill Jacket, paired with the Mariner Denim Striped Sailor Pants.  Next is the Day sail Striped Turtleneck paired with Twill Bermuda Shorts.  This too cute outfit is the Chambray Wrap Skirt, Cashmere Tee and espadrille wedge.  Lastly, and one of my favorites is the Piped Wrap Dress. 

Ralph Lauren, a favorite among preps since the eighties has great outfits for spring.  They are versatile, sexy and most of all cute.  These photos are from his Blue Label and Ralph Lauren Rugby.  From top to bottom-Paisley Halter Jersey Dress, Cotton Sea Scout Sweater, McLear Georgette Dress, Vell Jersey Necklace Dress, and the Classic Stretch Satin Trench.  The last look is very chic, very metropolitan.  It's a very nice look but to me you have to be a certain type to pull it off if you understand what I mean.  You can find these on the Ralph Lauren Link.

What's summer without a tube dress ladies?  So let's rock it huh?  Lilli has some very colorful and classical dresses like these.....

And by all means, don't forget that all too famous preppy pattern....the madras.  They just make you happy don't they?

Let's take a look at footwear.  When the weather gets warmer, we don't always have to put on the old standby.....the flip flop.  Spring is a good excuse to get yourself in step.

These lime green and white ballet flats are just tooo cute and oh so preppy.  You can find them at

Looking for an all purpose spring shoe that can handle the elements? LL Bean has got you covered.  Here is a number that every woman should have.  The vacation land sport Mary Jane and water shoe.  There are more colors and can be found on the LL BEAN link.

Looking for the original spring boat shoe?  The has two that I love.  First the original boat shoe and the canvas mule.

Another good summer shoe is the espadrille.  One examples is from 

Another example is from  It's the Burburry Ankle Tie Leather Espadrille. 

These last sexy numbers I threw in for good measure.  You can never have to many shoes.  And after all it's always fun to play around with them.  I'm not sure who makes these shoes but they were just too lovely to pass up.

Can you believe it?  Exclusive Jack Rogers thong sandal in Nantucket Red fabric, bone leather thong and sole.  in sizes 5 to 11 medium.  They look great with skirts, dresses, capris and jeans.

We all know that nothing says spring/summer like a cool pair of flip flops.  I'm always looking for the coolest pair.  Enter V.V. and Nantucket Noose.  These are my favorite places for flips.  Check them out. 

These are over sand permit flips from Nantucket Noose.  I have this exact pair and love them.  They are unisex and if hubby or boyfriend is a bit flamboyant, get them.  After you've gotten a pair for yourself of course.

V.V. Pin whale Flips.  Cute huh?

V.V. Nantucket Signs Flips.

V.V. Seahorse Flips.  You can count on the Vine giving you fun, sporty and whimsical items.

Personally I think there is nothing more feminine than a woman with a headband.  Not to mention they scream spring and can add color to any wardrobe.  At the you can buy some very creative and colorful headbands at a very nice price.  The Hyannis, The Nantucket and The Westport are my favorites.
I threw this pic in because it was sooooooooooooo cute and very well done.

What could be cuter than a ribbon watchband to tie your ensemble together.  Check these winners out.

This is a fine example over on  They have everything.  From belts and headbands, to key chains and clothing.

If you want a watchband that's a little dressier, there's a site that can handle that.  They're called  They even have watchbands in velvet.  Here's an example of their work.

Lastly, while out and about, you need to carry all your necessities right.  Well what could be more preppy than a tote.  And while you're at it, have the darn thing monogrammed.   First we have the Sunwashed Tote that can be paired with just about anything.  The Madras and the Open Top Boat and Toted.  They're all from LL Bean.  Check my links area.  They also do monograms

Yes spring is here and hopefully you're all ready.  I know I am.  I hope everyone has a safe and preppy spring.  If you have any fashion choices of your own to contribute, by all means do so.  See ya soon.

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