Chess

Chess: A thinking man's game with classic European pedigree.  Hard to get more WASP'y than that.
Chess: A thinking man’s game with classic European pedigree. Hard to get more WASP’y than that.

Since this is possibly the final weekend before world politics devolve into a Third World War what better time to highlight a pursuit that, perhaps more than any other, values strategic thought, deep calculation, psychology, and prudence.  Sadly I am most definitely not talking about 21st Century diplomacy… but rather the game of Chess.

Although come to think of it, maybe Chess could be the answer to this current crisis? The howtoWASP believes that war, and especially unnecessary war, is exceedingly detrimental to Western Civilization (and therefore WASP culture) and should be avoided if at all possible.

Rather than fight things out over the cities of Europe and Asia, why not settle this dispute on the chessboard instead?   How entertaining would it be to have President Obama challenge President Putin to a winner take all (or just the Crimea) game of Chess?  The broadcast rights alone would probably be enough to pay down a significant portion of the national debt.

Then again perhaps challenging a Russian to a game of Chess isn’t the wisest thing in the world?  It would be a bit like challenging a Norwegian in skiing, or an Irishman to drinking, or like the French challenging anyone else to an actual war…  Probably not a good idea.  But enough with the politics and back to the matter at hand, Chess!

Screech Powers was in Chess Club.  Enough said.
In the 1990’s Screech Powers was the face of Chess Club. Enough said.

Chess is kind of a strange topic because it straddles the line between the worlds of WASP culture and nerd culture.  In terms of historic pedigree, Chess has a lot going for it.  It was popular among the British, it’s seen as a noble intellectual pursuit, and often evokes images of civilized competition among students at a prep school or members of a social club.

Then again, over the past half century or so, Chess has definitely struggled with a reputation of being the preferred hobby of the kid you probably didn’t want to hang out with in school.

Today, there's a whole new style of Chess whiz.
Today, there’s a whole new style of Chess whiz.

Thankfully, that has been changing of late and Chess is becoming cool again.  Want proof?  Google the name of the current world champion, Magnus Carlsen, and you won’t see the stereotypical Chess nerd, but rather someone who would look perfectly at home selling Abercrombie & Fitch clothing at the mall.

So, with the social stigma disappearing, and the WASP cred as strong as ever, Chess is definitely something worth learning.

The History:

If you’re looking for historical pedigree, Chess is difficult to beat.  It is one of the oldest games on the planet, having been played in some form or another for neartly 2,000 years.  There is still debate over the earliest origins of the game, but credit is generally given to the Indians (the Asian variety) who played a game called Chaturanga as early as 300 A.D. Chaturanga was played on an 8×8 grid and featured different pieces that each had special attributes, more or less analogous to the modern Chess pieces of today.

By the 7th Century, Chaturanga had found its way to the Persian empire where it continued to gain in popularity and spread throughout the world.  Around the 9th Century the pastime began to pop up in Europe as well, most prominently among the Moors who introduced it into the Iberian Peninsula and what is modern day Spain.  It was during this time that the game, which had picked up the name “Shah” (Persian for “king”) began to be known as Chess.

How many games still around today were enjoyed by Members of the Knights Templar?  Not many, which is pretty badass.
How many games still around today were enjoyed by Members of the Knights Templar? Not many, which is pretty badass.

In the hundreds of years that followed, Chess spread quickly throughout Europe where it continued to evolve. During the 15th Century the modern rules for the game were adopted by the Spanish and Italians.  With small tweaks here and there, the game as we know it today was finalized in 1850.

It was during this European evolution that the aura of Chess as a gentleman’s sport was cemented in place.  Since the Middle Ages Chess has enjoyed a reputation as a noble pastime, where it was viewed as the game of choice for kings, knights, and other members of nobility.  It’s popularity and esteem continued to grow with the great thinkers of the Renaissance and continued into the Age of Enlightenment.  Benjamin Franklin himself went so far as to write an article praising Chess as a method of self improvement and for the virtues of strategy and thought it can instill in man.

In the Modern Age, since 1850, Chess experienced further explosions in popularity as rules for formal competition and rankings were set in place.  However, the good times would not last.  With the onset of the World Wars, and the Cold War that followed, much of the Western world lost interest in the game (it didn’t help that the Soviets dominated the wold competition during those years) and Chess settled into a new role as a niche hobby for those with more brains than braun.

But again, with the dawn of the the 21st Century, it appears those days might finally be behind us and Chess is poised to rise again.

The Game:

The standard starting position for a fresh game of Chess.
The standard starting position for a fresh game of Chess.

The best thing about Chess is that it follows the golden rule for great games:  It’s simple to learn, but nearly impossible to master.  It can be picked up quickly and played by just about anyone, yet subsequently provide a lifetime of challenge and enjoyment for those who seek to improve.  Chess is also one of the few games where chance plays no role in the outcome.  You win or lose based on your play alone and the winner is always going to be the player who commits the fewest errors.

If you’ve never played before, or if its been over a decade since your last game, then the only place to begin is with the fundamentals.

I won’t waste time reinventing the wheel here because there are plenty of great resources available where anyone can learn the basic rules of the game.  My personal recommendation would be to check out Chess.com, which offers great lessons for everyone, from the rank beginner to the Grand Master.  If you want to go the more formal route, there are plenty of books on the subject available for pennies on Amazon, or for free at your local library.

Once you know how the pieces move, you could theoretically begin playing immediately, just be prepared to lose, a LOT.  While there’s no substitute for in-game experience, I would highly recommend devoting at least some further study to the three main components of the game and the strategy and tactics behind them.  As a very brief overview, these include:

There are many different openings, but the howtoWASP prefers the English, for obvious reasons.
There are many different openings, but the howtoWASP prefers the English, for obvious reasons.
  • The Opening:  This covers the first 10 moves or so of the game.  Basically both sides are seeking to establish position and control the center of the board as quickly as possible.  Setting up a solid defense and protecting your king are also paramount.  The good news here is that since Chess has been played for centuries, most openings are set to an established script.  While there are only 18 possible opening moves (and really only about 5 that you’d ever want to use) there are hundreds of “book” openings to cover all the possible responses, re-responses, and so fourth that can follow.  Again, Chess.com provides a wonderful library of book openings.  Like anything else, all it takes is study and experience to recognize and play them.
  • The Middle Game:  This is where most of the action occurs.  The fight for position continues, but more pressing is the need to set up an effective attack, or defense to counter an opponent’s attack.  Most of the time the goal in the middle game is to force exchanges (trading pieces) that leave you with a material (having a greater number of and/or more powerful pieces left on the board) or positional advantage.  This phase requires much more thought and analysis than the opening as tactics begin to outweigh the strategic focus of the opening.   Players must calculate several moves ahead, taking into account many different pieces and possible combinations, to be successful.
  • A typical End Game scenario: short on material, long on options. A tacticians paradise.
    A typical End Game scenario: short on material, long on options. A tacticians paradise.

    The End Game:  Assuming that you didn’t blunder the game away in the middle (which is definitely possible, especially as a beginner) then things proceed to the final phase, the end game.  Here calculations become theoretically easier because there are often only a few pieces remaining (usually mostly pawns and kings), but it rarely seems that way in practice because of the sheer number of possible moves available on the open board.  Here tactics are paramount as even a slight mistake can lead to a disadvantage and eventual loss.  If you’re ahead or even at this point, you’re playing for the win.  If you’re down, then playing for a draw(tie) is probably your best bet.

Of course that’s a gross over-simplification of the game, but those are the basics.  As I said, the only way to truly learn and get better is to sit down and play as much as possible (which thankfully is much easier in the internet age). Fair warning, it will probably take about 6 months of regular play before you start to really understand and win games on a consistent basis, but once you reach that point, you will have developed a new skill for life.

So what are you waiting for?  In this crazy world, where attention spans increasingly need to be measured on a nano scale, and shows like Teen Mom and Jersey Shore makes up a disturbing proportion of the entertainment content available, wouldn’t it be nice to slow down and give your brain a bit of proper intellectual (and supremely WASP’ish) stimulation?

As we know, Benjamin Franklin believed that Chess was an excellent resource for self improvement, and with that in mind, I will close with what I believe is the number one life lesson taught by Chess:  No matter how well you prepare, or how far you’re ahead, we are all but one blunder away from complete and unmitigated disaster.   Perhaps both Obama and Putin would do well to remember that…

Next Steps:

  • Assuming you’ve learned the basics, the best thing you can do is get out and play some Chess.  While in-person games are classic and always fun, the internet has opened up a whole new range of options.  My favorite offering from Chess.com is the ability to play online, turn based games (typically up to 3 days per move) that allow you to play at your own leisure, against thousands of players of every skill level across the globe.
  • When you play, try to play against opponents who are better than you.  While it’s always enjoyable to win, if it’s against a lessor player, you’re probably not learning much in the process.  The flip side is that while losing sucks, you can actually learn a lot if you pay attention.  Remember, it takes about 6 months to really pick things up and become competitive.  Don’t get discouraged!
  • Nothing classes up the joint like a dedicated Chess table.  Although all you really need is a good board and set.
    Nothing classes up the joint like a dedicated Chess table. Although all you really need is a good board and set.

    While online Chess is great, you’ll also want a good, old fashioned Chess set in your home. Why?  First of all because it will make you look smart and sophisticated when guests come over.  Second, it will allow you to play more games in person.  And lastly it can be a valuable analysis tool to visualize and play out scenarios in your online games.

  • Keep learning.  While there’s no substitute for actual play, reading books and watching video lessons on advanced strategy and tactics can really help improve your game. This is obviously more beneficial for experienced players, but if you’re like me, once you catch the bug, it’s hard to stop.
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Port

Port: the greatest, and WASP'iest, of all fortified wines.
Port: the greatest, and WASP’iest, of all fortified wines.

After a hiatus, I’m pleased to announce that the how to WASP is back!  And to celebrate its return to the blogging world, I’ve decided to highlight one of my all-time favorite WASP’y indulgences: Port.  Now that I think of it, Champagne would have probably been a better celebratory choice… but that will have to come later.  So for now, Port!

No, we’re not talking about the seaside variety (although confusion could be understandable given the focus of this blog), but rather the undisputed king of all fortified wines.  When it comes to dining like a WASP, there is perhaps no better way to finish off a fine meal that a good glass of Port.  However, the subject can be surprisingly complicated, so it’s important that you know the basics before you can order, and most importantly enjoy, that tote of Cockburn (see Next Steps below) with confidence and pride.

What Exactly is Port?

Excellent question!  And to provide and answer, it is necessary to take a brief trip back in time.  Port, like most things WASP’y, is a product of the British and a dislike of the French.

As most students of history will know, England spent a good portion of the last millennium fighting the French.  However, by the 17th Century they ran into a problem.  The Brits had developed a taste for Continental wine, but thanks to their most recent war with the French, they suddenly found themselves cut off.  Their solution: simply get wine from Portugal (one of their few wine producing allies on the Continent) instead.

A pretty slick solution, but another problem quickly became evident; Portuguese wine proved to be much less stable than its French counterpart   As a result, the Portuguese wine would spoil during the extended sea voyages back to England.  Fortunately for all of us, the classic sense of British stick-to-itiveness prevailed.  They discovered that by adding a small amount of brandy (a process known as fortification) to the finished wine, it could be made stable to endure the long trip back to England and the wine we know as Port today was born.

A Port Primer

Now, you may be thinking “So that’s why it’s called Port, it’s from Portugal!” but you’d be wrong.

The namesake of Port is actually the city of Oporto, located on the Atlantic at the mouth of the Douro River.  This city is where the English set up their first Port Houses to distribute the newly invented wine and where they have remained ever since.  In fact the world’s first Port producer, Warre (established in 1670) is still operation there today!

The Douro Valley, one of the most scenic wine regions on Earth and where Port is born.
The Douro Valley, one of the most scenic wine regions on Earth and where Port is born.

So Port wine comes from Oporto, which makes perfect sense, but it gets a little more complicated.  While Port is distributed from Oporto, the wine is actually produced about 50 miles up the Douro River in the hot and ruggedly mountainous Douro Valley.  This is where the grapes are grown and the wine is fermented.  It’s then packed into barrels and sent down the river to Oporto, where it’s fortified, aged, bottled, and eventually shipped to Port lovers all over the world.

Styles of Port:

Port has two constants: It’s always sweet, and (almost) always red.  Beyond that, however, the varieties and styles of Port are nearly endless.

Part of that variety is thanks to the sheer number of grapes that are permitted in Port.  In most blended wines, you’ll see 3-4 grape varietals, tops.  In Port there are more than 80!  Although in practice the most common types used are Tempranillo, Touriga Nacional, and Tinta Barroca.

While the grapes certainly play a role in nature of a Port, it’s really the style of wine that determines its ultimate character (and price).  While there aren’t quite as many styles as grape varieties, there is still a lot to know, so pay attention!  Below are some of the most common Port styles, listed from lightest to fullest.

  • White Port:  White Port is just that, Port made from white grapes.  It’s not very popular and much more difficult to find that the red variety.  It’s also generally known to be not anywhere near as good.  I confess that I’ve never tried it myself, but I’ve heard that it’s best use is when served ice cold as a summer aperitif.  Not really in the same league as red Port, but I included it here for the sake of knowledge.  
  • Ruby Port: The youngest and simplest version of Port.  Just like the name implies, its typically deep red in color.  It’s also fruity, sweet, and easy drinking.  The wine itself is aged about 3 years in wood and is ready to drink as soon as it’s released.  In fact the younger it is, the better it will taste.  Ruby Port is also the cheapest Port available and often a great introduction to the wine.
  • Tawny Port:  By far the most popular and common type of Port you’ll encounter in an after dinner setting.  Tawny Port is generally a blend of good quality wines that have spent a long time aging in oak barrels.  While in the wood, the wine softens and turns to a pale garnet or brownish color (it tawnies, hence the name).  One point of
    Tawney Port is the most common style available.  Note the 20 year marking on the bottle, indicating the average aging of the wine in the blend.
    Tawney Port is the most common style available. Note the 20 year marking on the bottle, indicating the average aging of the wine in the blend.

    confusion is the age marked on the bottle, typically 10, 20, 30, or 40 year old.  This is NOT the age of the wine in the bottle, but rather the AVERAGE time the wines used in the blend have spend aging in barrels.  Tawny Port is generally less sweet and fruity than Ruby Port and offers more complex earthy/nutty flavors.  It varies wildly in quality and price, from less than $10 to well over $100.  Tawny Port is ready to drink upon release and won’t get better with age.

  • Colheita Port:  A sub-variety of Tawny Port where the blended wines are all from a single vintage, usually listed on the bottle.  In other words the wines from a single year are placed in wooden barrels and aged (tawnied) for many years before being bottled.  It’s generally better quality than regular Tawny, but not very common.
  • Late Bottled Vintage (LBV) Port:  This Port is made from a single, generally lesser quality, vintage year.  The wine is fermented and then aged in wooden barrels for anywhere from 4-6 years before being bottled.  The result is a darker, less soft, and much fuller style Port than the Tawny.  LBV Port is marked with the vintage data and ready to drink as soon as it’s released.  It’s fairly easy to find and you can expect to pay $20-30 for a half bottle, making it a fairly good value.
  • Vintage Port:  The crème de la crème of Ports.  Vintage Port is only made during the very best years and from the very best grapes.  It is aged for a scant two years in oak
    Some older bottle of Vintage Port.  Amazingly these are still drinkable and probably quite good.
    Some older bottle of Vintage Port. Amazingly these are still drinkable and probably quite good.

    barrels before it’s bottled and sold, which is not nearly enough time for the wine to soften or fully develop.  As a result, Vintage Port requires an enormous amount aging in the bottle before it’s ready to drink, typically around 20 years after the vintage, but sometimes even longer (70+ years) depending on the year!  However, the wait is worth it.  Vintage Port is not only one of the best dessert wines in the world, it’s one of the best wines period.  It’s extremely full bodied, rich, and chock full of flavors such as nuts, toffee, chocolate, and spice.  Recent release bottles of Vintage Port are fairly easy to find, but are expensive at $50-$100 a bottle.  For properly aged (and ready to drink bottles) expect to pay around $100 or more, sometimes much more…

Enjoying Your Port

OK, enough with the academic stuff, now it’s time to for the fun part: drinking Port.

As was mentioned earlier in the post, the good WASP will enjoy a glass of Port as an after dinner drink, which means you should too.  Because Port is a sweet wine, it’s the perfect compliment to dessert.

Truth be told, nothing goes better with a good glass of Port than a simple hunk of dark chocolate, but in general the rule is that Port will pair beautifully with any dark colored dessert.  In other words if chocolate or dark berries are listed in the ingredients, you’re good to go.  What if you’re having a light colored dessert?  Sorry, you’ll just have to wait for the post on Sauternes…

Proper Decanting is necessary to aerate and remove sediment from Vintage Port.
Proper Decanting is necessary to aerate and remove sediment from a Vintage Port.

Of course Port can also be enjoyed without dessert on its own.  Or for a truly classic paring, try a glass with walnuts, or any strongly flavored cheese (Bleu cheese is best).

If you’re serving Port at home (or just want to impress your friends/annoy your waiter) it should be served at cool room temperature, or roughly 65 degrees.  Most Ports can simply be poured and enjoyed, but properly aged Vintage Ports (don’t even think about serving otherwise) requires several hours of decanting to remove sediment and allow the wine to properly aerate.  It may seem like a lot of work, but just do it, otherwise you’ll have wasted that $100 investment and worse yet, cast yourself as a WASP noob in front of all your friends.

Port-ing Thoughts

Port really is a wonderful wine and, unlike most things WASP’y, actually represents a phenomenal value.  Port’s popularity has waned in recent years, which is bad for Port producers, but great for you as a consumer since low demand = low prices.  Good quality Ruby and Tawny Ports can easily be had for less than $20.  Even an expensive Port (like a $100+ bottle of Vintage Port) is a great deal considering a comparable quality dry red wine will cost hundreds, if not thousands, of dollars.

Another value consideration is that unlike normal wines (that will start to turn bad a mere day or two after uncorking) Port will stay good for weeks, or even months, after opening.   The reason of course is the fortification (adding brandy to wine to preserve it) that makes Port so special in the first place.  After all, if it could survive weeks in the cargo hold of a ship, a couple days on your shelf is nothing.

Oh, and one last parting word of warning…  Because Port is a fortified wine, it will typically have an alcohol content that is far higher than normal table wine, usually anywhere from 15-25%.  In other words, watch out!    Generally speaking, a serving of Port is about half that of a normal glass of wine, so pour and enjoy accordingly.  Cheers!

Next Steps:

  • The first step is obvious: Go out, buy some Port, and drink it! I recommend starting with a bottle of Ruby Port and working your way up from there.  The beauty of Port is that it’s usually available in half bottles and cheap enough to try a bunch of different brands and styles without breaking the bank.  And if it’s something you don’t care for, just pour it out or cork it up for a couple weeks till you can offer it to someone who does.
  • Real Port only comes from Portugal, but that hasn’t stopped others from imitating the
    Renwood, out of Amador, CA, makes an exceptional Zinfandel based Vintage Port.
    Renwood in Amador, CA makes an exceptional Zinfandel based Vintage Port.

    style.  Many wine producers (particularly in the US) make at least one port-style wine, often with very good results.  Typically these wines are made with local varieties (Zinfandel makes particularly good Port wine) and will be sold as Ruby or sometimes LBV style Port.  You’ll rarely see Tawney or Vintage offerings.  Some makers can call their wines Ports (via grandfathered rights, otherwise Port is trademarked and can only be used for real Port) but most will not.  You can identify them by their smaller bottles, alcohol content (around 20%), and usually find them along with the other fortified wines at the wine shop.

  • Most high end restaurants will include Port (almost always Tawney, but sometimes Ruby’s or Vintage as well) on the dessert menu, which you should absolutely try.  A popular offering is from a producer called Cockburn.  This is a wonderful choice, but you can save yourself some embarrassment by using the correct pronunciation: COH-burn.  Enjoy!

The Top-Sider

A Golden Retriever and a well worn Top-Sider. A little piece of WASP heaven.

More often than not when discussing how to dress like a WASP, the conversation inevitably turns to business or other semi-formal attire. And while it’s true that knowing how to dress up properly is a key component of WASP culture, we must keep in mind that knowing how to properly dress down can be just as important.

And when it comes to casual attire, there is one item in particular that no self respecting WASP should ever be without: a pair of Top-Siders.

Now, I’ll be the first admit that some WASP’y attire isn’t exactly practical or cost effective.  There are, for example, only so many opportunities to show off that new Madras suit and not be mistaken for a hobo…  However, that’s definitely not the case with Top-Siders.  In fact they’re actually one of the most practical purchases you can ever make.

Why?  First consider that the Top-Sider (also known as the boat shoe or deck shoe) is perhaps the most versatile footwear option available on the market today.  Think about it, whether it’s in the office or on the beach, the Top-Sider is equally at home.  They’re perfectly appropriate just about anywhere and for anything.

Also handy is that they never go out of style.  Minor variations come and go, but the basic deck shoe has remained essentially unchanged (and a best seller) for nearly 80 years.  These days they seem to cycle between preppy niche item and mainstream fashionable.  Either way you can’t go wrong.

Dawn of the Deck Shoe:

Paul Sperry in 1935

Rather the typical Anglo-Saxon background associated with much of WASP culture, the Top-Sider is uniquely a product of American ingenuity.   The idea for the shoe was first conceived by a man named Paul Sperry.  During a cold Connecticut winter, Paul noticed that his dog Prince seemed to have no trouble running across slick snow and iced covered surfaces and became curious as to what made that possible.

Upon further investigation he noticed the pattern of groves and cracks in his dog’s paws and suspected they were the secret to Prince’s superior traction.  Sperry set about replicating the pattern by using a razor to score groves into a rubber shoe sole and the rest is history.  By 1935 the design was refined into the scalloped pattern of cuts (like you’ll find on any pair of deck shoes today) and the Top-Sider was officially introduced.

As the name implies, the Top-Sider (referring to the outer or “top side” deck of a boat) was originally introduced as a boating shoe that would allow sailors like Paul Sperry to maintain traction in even the slipperiest of conditions.  The shoes proved to be highly effective and over the following decades became a WASP favorite both on and off the water; as their association with boating culture sowed appeal among the general preppy set as well.

The natural element of the Top-Sider. Thanks to their uniquely designed sole, they'll maintain traction on even the slickest of surfaces.

What to Buy:

OK, so you’re on board (get it?) with the idea that you need a pair of deck shoes.  Now comes the task of actually going out and buying them.

The good news is that just about every major shoe company out there makes at least one variation of the basic Top-Sider.  The bad news is that every shoe maker makers at least one variation… You get the idea, how are you supposed to choose?  There really are a huge range of options out there between different manufactures, levels of quality, material, color, etc…

My recommendation: stick with the classic.  That means going with the original Sperry Top-Sider.  They’re the real deal, last for years, and available everywhere.  They’re also fairly inexpensive compared to many of the deck shoes offered by other brands.

In terms of material I’d suggest going with the basic leather in some shade of brown or tan.   For the soles stick with the basic flat rubber bottom.  They don’t offer a lot in terms of support, but then again you won’t be wearing them to run a marathon…  If you want to go really traditional, get the soles in white (originally designed to not mark-up decks).  Although I’ll confess that I actually prefer the colored variety.

The classic version of the Sperry Top-Sider. Note the simple brown leather construction, rawhide laces, and white "non-marking" soles. If you want to go authentic, this is it.

Again, stick with the classic and you really can’t go wrong.  However, once you’ve got your classic pair of Sperry’s, feel free to experiment.  Higher end dress models, canvas, suede, different colors, there are a myriad of options from which to choose.  Just try not to stray too far from the original if you want to maintain that WASP’y image.

How to Wear:

This may seem like a no-brainer and in some ways it is.  For the most part you can simply throw on your favorite pair of deck shoes no matter what you’re wearing and you’ll look fine.  After all, that’s a major part of the appeal of the shoes to begin with.

However, in order to really do it right, I believe there are some general guidelines you should follow when wearing Top-Siders.  In my opinion deciding when and where Top-Siders are most appropriate depends largely on the age and condition of the shoes.  The breakdown goes as follows:

Like New (100-75%) – Generally when the shoes are new an pristine.  They’re unscuffed, unstained, and maintain their original form.  They’ve never really been exposed to water so the leather is still soft and supple.

In this condition Top-Siders are best worn in nicer settings, such as the office, out on the town, or when dining at a decent restaurant.  Think of them as being on par with a pair of loafers.  They can be worn with socks (only with pants, please) or without.

A well worn pair of Top-Siders that have seen lots of time on the water. This how deck shoes should look.

Worn (75-25%) –These are shoes that have begun to show their age and/or good use.  They’ll be worn, scuffed, and probably lightly stained.  They’ve seen lots of sun and water and taken on a flater shape.  The leather is stiffer and the seams might also be separating a bit at the tops.

While it may not sound like it, this is the ideal Top-Sider condition.  It shows that the shoes have been used as intended (out in the elements) and gives you that classic preppy/casual look.  What you loose in ability to wear in more formal settings, you more than make up for in terms of all around utility.  Out on the weekend, around the house, to the beach, at the pool, etc…  The list is endless.  At this stage of life, sockless is the only way to go.  (For instructions on how to weather your deck shoes, see “Next Steps” below.)

Near Death (25-0%) – The shoes have become heavily worn with lots of scuffs and stains, maybe even some tears as well.  The laces have probably broken at some point (simply retie them together) and some of the seams have begun to open up.  The shoes are severely weathered and the interior is frayed or coming apart.  The soles have hardened, cracked, and no longer provide grip.

The sad fact about heavily used shoes is that they all eventually wear out.  Top-Siders are no different, however that doesn’t mean they’re ready for the garbage.  While you can no longer wear these shoes out on the town, they are still great to have around the house for garden chores, or perhaps for use at the beach or pool.  When you need a simple pair of shoes that you don’t really care about damaging or losing, these are the way to go.

Once your Top-Siders have worn away to nothing, it’s time to go out and get another pair and then repeat the process.  My guess is that once you get used to wearing them, you’ll be hooked for life.

Next Steps:

Even high end manufacturers now make deck shoes. This version by Salvatore Ferragamo will set you back $300.

1) If you don’t already have a pair, head out to the store and buy some.  Almost every major shoe store or department store will carry Top Siders and/or other styles of deck shoes.  Pricing is just about the same everywhere, but sometimes you can find a deal for $10-20 off.  In general expect to pay around $70 for a pair of Sperry Top-Siders.  Some brands cost less, some cost much more.

2) Check out the Sperry website to get an idea of the ranges and style available.  As I said, stick with the classic for your first pair.  After that, sky’s the limit.

3) Weather your Shoes:  If you want your Top-Siders in the desirable “worn” phase of life, there are ways to speed up the weathering process.  My dad often asks me to take his new pairs with me when I go sailing, which is hands down the best way to weather your deck shoes.  If you don’t have access to a boat, you’re not out of luck.  It’s an easy process to replicated on shore.

Simply take the shoes and dunk in completely under water (salt water if you really want an authentic look, but make sure to rinse with fresh water before drying).  Don’t worry, as long as you have a basic leather and rubber model, the shoes are designed for this kind of abuse.  Once the shoes are soaked, take them out and let them dry completely in the sun.  You’ll notice they’ll be very stiff at first, but will quickly soften out with wear.

Sometimes one soaking is enough, or you might have to repeat the process 2-3 more times.  But eventually you’ll have a nice pair of perfectly weathered Top-Siders ready for casual WASP duty anytime, anywhere.

4) Once you have your shoes purchased and weathered the last step is simple, just thrown them on and enjoy!

The Sunday Brunch

When it comes to upscale socialization and drinks before 5:00, brunch reigns supreme.

With Easter Sunday nearly upon us, what better time to highlight that WASP’iest of all meals: Brunch.  Aside from being one of America’s best loved portmanteaux, the mere mention of bunch is sure to conger up images of the classic WASP lifestyle.  Upscale social interaction, fancy restaurants, preppy attire, and of course, the hands-down best excuse to drink during the middle of the day.

That being said, brunch basics are a must-know for any serious student of WASP culture.  The good news is that learning to brunch (yes, it’s a noun and a verb) properly is one of the easiest lessons you’ll find on the how to WASP.  Really all that’s required is knowing when and where to show up, what to consume once you’re there, and then going out and experiencing it for yourself.  But first, a little history…

Brunch Beginnings:

Like most WASP’y, it should come as no surprise that the institution of bunch traces its origins back to Great Britain.  According to the Oxford English Dictionary, the term was first used by a man named Guy Baringer in an 1895 article he wrote for Hunter’s Weekly titled Brunch: A Plea.

The traditional English Sunday dinner doesn't exactly qualify as "light" fare.

Prior to Mr. Beringer’s plea, the typical English Sunday consisted of an early breakfast and morning church service followed by a formal Sunday dinner.  Now, it’s important to note that in those days, dinner didn’t mean the same thing that it does today today.  Rather than being the third and largest meal of the day served in the evening, dinner was more akin to a substantial late lunch, served around mid-afternoon.  It was largest meal of the day and typically followed by a smaller evening meal called supper.  The English Sunday dinner in particular was often an especially heavy meal consisting of substantial meat dishes and other savory offerings.

If that sounds a bit daunting, you’re not alone.  Guy Beringer thought exactly the same thing and in Brunch: A Plea he proposed an alternative:

Instead of England’s early Sunday dinner, a postchurch ordeal of heavy meats and savory pies, why not a new meal, served around noon, that starts with tea or coffee, marmalade and other breakfast fixtures before moving along to the heavier fare? By eliminating the need to get up early on Sunday, brunch would make life brighter for Saturday-night carousers. It would promote human happiness in other ways as well. Brunch is cheerful, sociable and inciting. It is talk-compelling. It puts you in a good temper, it makes you satisfied with yourself and your fellow beings, it sweeps away the worries and cobwebs of the week.

Remarkably, this more than a century old proposal almost exactly describes brunch as it exists today.  Essentially a lighter mid-day meal that serves both as an informal social occasion and a reprieve from having to get up too early after a little weekend excess.

Over the course of the 20th Century brunch steadily caught on United States.  It also developed its close association with WASP culture as the meal became a favorite post-church social activity among the upper class establishment.  The golden age of brunch probably occurred around mid-century when each Sunday millions of Episcopalians across the country would head out from church on a weekly trek to the nearest restaurant to eat, drink, and socialize with friends.

While church attendance gradually declined in the decades following World War II, the institution of Sunday brunch stuck around.  Partly out of respect for social tradition, partly out of the appeal of not having to get up too early, and partly out of the aforementioned excuse to drink before five o’clock, brunch thankfully still remains relevant today.

A Quick Guide to Brunching Like a WASP:

As mentioned earlier, there’s really not too much involved when it comes to brunch, but there are couple pointers for first timers looking to do it right.  Remember that brunch is by nature informal and fun, so please consider the following general guidelines rather than absolute rules.

What Day? – Brunch was traditionally served on Sunday and that remains the case today.  Technically you could have brunch any day of the week, but you’ll find most restaurants offering a specialized brunch menu will only offer it on Sunday.

Today most Americans only go to brunch as couple times a year, usually for special occasions like Mothers Day, Valentines Day, or Easter.  However, there’s really no need to limit yourself.  I would encourage you to have brunch as often as you like, every week if possible!

What Time? – Every restaurant is different, but usually you’ll find brunch being offered from 10:30 AM to 2:00 PM.  Sometimes it may begin a little sooner, or end a little later.  In general if you plan on showing up sometime during the late morning you should be OK.

Where to Go? – To do brunch right, you’ll want to find a nicer, fairly upscale, restaurant.  Preferably one that offers a dedicated brunch menu, or at the very least offers both breakfast and lunch options.  This doesn’t necessarily mean the most expensive place in town, just someplace nice.  Could you simply catch a late breakfast at Denny’s?  Sure, just keep in mind you’ll be straying a bit from the WASP ideal.

The good news is that since brunch is not a formal meal, most restaurants that might normally be out of your price range for dinner typically offer much more reasonable prices for daytime fare.  Some places will even have special deals just for brunch.  A little research can really pay off.

The general sort of upscale/casual atmosphere you're looking for when scouting a brunch locale.

What to Wear? – Back in the old days it was easy, you simply dressed in whatever you wore to  church.  Today however, the key is balance.  On the one hand brunch is supposed to be a somewhat casual occasion.  On the other it’s still a traditional social event taking place in a nice setting.    If you do decide to dress up, you won’t look out of place, but in general you can get away with a sort of preppy/casual style.  If you’re having trouble deciding between outfits, always err on the side of a little too formal.

You'll never go wrong with Eggs Benedict!

What to Eat? – One of the great things about brunch is the shear selection of choices available.  Because you’re in between breakfast and lunch, it’s appropriate to order either.  Eggs, Bacon, Waffles, Pancakes, Salads, Sandwiches… sky’s the limit.  Brunch is the one meal where everyone at the table can get just about anything they like, all served at the same time.

Personally I favor the breakfast side of the menu.  In fact my go-to selection is Eggs Benedict, which I consider to be brunch royalty.  You get a little bit of everything on a single plate.  The eggs, sausage, and English muffin suggest a casual breakfast while the hollandaise sauce brings a touch of rich decadence to the party.  If you can’t decide on what to get, you’ll never go wrong with Eggs Benedict.

What to Drink? – Brunch offers one of the few socially acceptable excuses to drink in the middle of the day, so you should definitely take advantage!  The only catch is that you’ll want to stick to a few pre-approved choices to avoid standing out.  Translation:  Save the beer and martinis for happy hour.

Basically there are two options: The Bloody Mary and the Mimosa.  Fortunately what you lose in quantity, you more than make up for in quality as both are excellent options and perfectly suited to brunch dining.  For those who many not be familiar with one or the other:

    • Bloody Mary: A savory tomato juice and vodka based cocktail with spicy kick.  It’s a heavy duty drink that can go with just about anything and is a true WASP classic.  Find out more here!
    • Mimosa: A sweeter cocktail of orange juice and Champagne, mixed in a ratio of 1/3 juice to 2/3 wine.  Technically if it’s not Champagne (with a capital C), it’s not a Mimosa, but these days any sparkling wine has become an acceptable, and far more common, alternative.  Mimosas are best enjoyed with egg and mushroom based dishes.
Your brunch cocktail options: Mimosas (left) or a Bloody Mary (right). You really can't go wrong with either.

That’s really all there is to it.  Stick to the guidelines above and you’ll be out brunching like a pro in no time!

Next Steps:

  • Again, this one’s easy, just grab a few friends this (or any) Sunday and have brunch!  Even better, set up a standing weekly brunch and turn it into a new tradition.
  • While Easter brunch is a great tradition, and one I encourage you to try, there’s something to be said for the “off” weekends as well.  By off weekend I mean any Sunday that’s not Mothers Day, Valentines Day, or Easter.  The crowds will be much thinner and the atmosphere more casual and conducive to socialization.
  • Put together a brunch appropriate wardrobe.  While looking sharp for brunch is an obvious benefit, having a go-to preppy-casual outfit can serve you well in a host of other situations.  In fact I’d call the preppy/casual look one of the most versatile dress options today.  Not sure where to start?  You can’t go wrong at Brooks Brothers.
  • Bon Appetite and Happy Easter!