Preppy Footwear

Of course, no outfit is complete without proper footwear.  I've decided to provide a list of the best preppy shoes.  Different shoes go with different outfits and colors, but the best kinds are the ones that will go with most anything.

 The ultimate preppy shoe will always be the top-sider boat shoe, made famous by Sperry (pictured left).  There have been many cheap knock offs such as Island Surf, but Sperry's are the real top-siders.  Their classic brown color means they can go with just about any outfit, be it formal or casual, although too formal will warrant something more dressy, such as wingtips.  They were originally designed to be worn on boats.  It stands to reason that if your dad just spent half a million dollars on a boat, he's not going to want you marking up the deck with your shoes.  Thanks to the non-marking souls of top-siders though, that problem has ceased to exist.  They come in many colors, but with shoes like these, you really can't go wrong.  Sperry's can even be found at J Crew, a store that doesn't always carry products from different labels.

H.G. Bass also features a line of good boat shoes, but their most notable creation is the Weejun Penny Loafer (pictures right).  Although more formal than top-siders, Weejuns can also go with most outfits, although black may be too formal for casual occasions.  Brown weejuns tend to go better with most things.  These shoes come in many colors and patterns, from the classic solid colors such as brown and black to more daring patterns such as stripped, denim, or even plaid.  Plaid weejuns are great shoes (I own a pair myself) although they can be difficult to match with certain shirts and pants or shorts.  That said, If you want an eye catching shoes, there's no better model out there.  Anyone who ever watched "Mr. Rogers" may recall that the star of that shoe wore Penny Loafers.  These shoes were popular in the 1970's but thanks to Bass, their making a come back.  As a side note, if you walk around with an actual penny in the front compartment, it won't fall out.  I know from experience.  The ultimate formal shoe will always be the wingtop, though.

Of course, some occasions call for sneakers, and that's where Keds come in.  These shoes were popular in the 1940's and afterwards, but now their making, or have made a comeback, which is great.  Keds look good, and their comfortable, fine for most casual athletic activity.  Vans, which are similar to Keds and come in more colors, are also acceptable, and they are
even available at J Crew (pictured below).

Preppiest Clothing Brands and Labels

They say the clothes make the man (or the woman), and in the preppy culture, that's certainly true.  The way someone dresses is typically the first indication of weather or not they are preppy.  That is not to say that everyone who wears an oxford shirt, a navy blue blazer, or nantucket reds is a prep, but just about any and all New England preps tend to dress in a similar fashion and it is very upscale.  Almost all prep schools that don't have the word "waldorf" in their title have uniforms that require ties, so all prep schools students learn to dress themselves in high school.  As many are at boarding school, they have to.  Different clothing brands cultivate different images and just because something is expensive doesn't mean it's preppy (i,e Abercombie & Fitch).  The classic clothing brands, though, will always cultivate a strong, preppy aire.

Ralph Lauren is very likely the most popular clothing brand in the field of preppy clothing.  They perfected the polo shift and all their clothes are top-notch, expensive as they many be.   All their shirts, like the one pictured below, are classic preppy, be they oxford, polo, henley, or even athletic apparel.  Their pants, of course, all the various chinos, kakkis, and even denim are top of the line and they also feature great shoes of all types, from loafers to boat shoes to sandals and flip-flots.  Plenty of preppy accessories to, such as pocket squares, keychains, and baseball caps.  At a store like Ralph Lauren, really anything is preppy.  Their polo player logo is an absolute preppy icon.

If you want to talk preppy though, Brooks Brothers you really can't beat Brooks Brothers.  Brooks Brothers features all the same clothes as Ralph Lauren, and even goes beyond with their items such as Cricket Vests (classic old school preppy) and books on how to be a gentlemen at the counter.  As great as their clothing is, though (I particularly find their sweaters to be especially comfortable), Brooks Brothers went above and beyond as far as preppy goes, when they laughed their "Great Gatsby Collection" in May 2013, prior to the release of the film.  They also began carrying copies of the book in store.  As expensive as this line was, for any Fitzgerald buff or just any preppy aficionado in general, they really are a must have.   I think the picture below will explain why.

I mean, seriously, who wouldn't want to be seen wearing that red and white stripped regatta blazer?  The brown and white wingtips tempted me as well.  Their clothes are absolutely fantastic and you don't have to be a Brooks Brothers model to pull them off...you just have to be Jay Gatsby himself in order to afford them  (It's worth mentioning that F. Scott Fitzgerald himself, one of the greatest preppies to have ever lived, shopped at Brooks Brothers in his day). Gatsby had all his shirts send to him from England, but if you can't work that, Brooks Brothers isn't a bad alternative, at all.  There can be no question that this is the sort of clothing Gatsby would have worn.  People then (at least in West Egg) had such great fashion taste.  Why couldn't I have grown up in that era?

Ralph Lauren and Brooks Brothers are just two of the many preppy brands our there.  That said, it is important to know which one as classic preppy and which ones are new wave pretenders.  J Crew and Lacoste should also be acknowledged.  Lacoste may not be quite as formal as Ralph Lauren or Brooks Brothers, but their clothing is great.  Their polos are top-notch and their logo, the signature alligator (pictured right) is as well known as the Ralph Lauren polo player.  J Crew may have a slight new wave/almost hipster (shudder) edge to it, but the edge is very slight and their clothing is more formal than Lacoste.  Their chinos, which come in just about every different color, are fantastic, and they produce perhaps the most comfortable v-necks.  Banana Republic deserves an honorable mention, as does Vineyard Vines.  Nantucket Reds will always be the ultimate preppy pants though.  The beautiful island of Nantucket (a popular vacation spot for wealthy new englanders i,e a preppy stomping ground in the summer) is home to Murray's Toggery Shop, where the original Nantucket Reds can be found.  It doesn't get any more authentic than that.  Don't be fooled, though.  Brands such as Land's End and Eddie Bauer are NOT preppy, as similar as their clothes may be to those you'd find at L.L. Bean.  Avoid brands such as Abercrombie & Fitch, American Eagle Outfitters, and Aeropostale...that's frat boy attire, and not the kind of frat a true prep would join.

Top Men's Preppy Clothing Labels (not ranked in order)
Ralph Lauren
Brooks Brothers
J. Crew
Lacoste
Vineyard Vines
Banana Republic
J Press
York Street
Tommy Hilfiger
G.H. Bass
L.L. Bean
Barbour
Smathers and Branson

For Footwear
Sperry
G.H. Bass
L.L. Bean (for their signature Duck Boots)

Honorable Mention
Nantucket Brand
The Gap
Tuckernuck
Van Heusen
U.S. Polo Association (USPA)


Brands to Avoid
Abercrombie & Fitch - We all know how CEO Mike Jefferies feels about large or "ugly" as he calls them, people buying his clothes.  Multiple lists of reasons not to shop there can be found here - http://www.huffingtonpost.com/news/mike-jeffries

Hollister - Abercombie's ugly cousin...and the surfer clothing is very west coast...notice how their website is divided into "Dudes" and "Bettys" and all their colons are named after places in Southern California.

American Eagle Outfitters - Thinly, cheaply disguised Abercrombie clothing.

Aeropostale - A poor man's American Eagle.

Land's End - A poor man's LL Bean.

Eddie Bauer - Decent chinos, but that's it as far as clothing goes.  Good for outdoor supplies, though.

The East Coast Prep

As a lifelong native of a wealthy Massachusetts "money town," and a prep school student alumn, I know full well that the east coast, more specifically New England, is the bastian of the classic American preppy culture.  No disrespect to the west coast, but as far as preppy goes, it simply can't compete with the east.  Let's look at some facts.

The term "prep" comes from the word, preparatory, and refers to someone from a college preparatory school.  Every true prep comes from, or came from a private college preparatory school and the east coast can only be described as America's prep school hotbed.  When thebestschools.org listed "The 50 Best Private Day Schools in the United States, 8 out of the top 10 were located on the east coast.  Congratulations to New York's The Trinity School for being voted number one.  For the complete list see the following link.  http://www.thebestschools.org/blog/2013/04/30/50-private-day-schools-united-states/.

Trinity is only one, though.  The Kennedy family has been described as the "truest American royalty," and former president John F. Kennedy, the most notable member, is an alum of Connecticut's Choate Rosemary Hall (pictured), arguably one of the most prestigious prep schools not just on the east coast, but in the country. Before that, he attended the Riverdale Country School, a very highly respected all boys prep school in New York City.  Before John arrived at Choate, his elder brother Joseph Kennedy Jr. attended and was a star football player as well as a leading student before attending Harvard University.  In his senior year, John was voted "most likely to succeed.  I think it's safe to say that when his classmates voted for him, they made the right choice.  It is worth mentioning that Kennedy attended private schools all through his academic career, starting with Brookline's The Edward Devotion School and ending, of course, with Harvard University, like all the other Kennedy men.  His younger brother, Robert Kennedy, who almost became president and served as John's attorney general, attended Milton Academy in Massachusetts (pictured).  Like his brothers before him, he too attended Harvard University.

Suffice it to say, the wealthy and powerful Joseph Kennedy Sr, who could could have sent his many children anywhere in the country, was a steadfast supporter of prep schools.  It clearly had it's merits, though, when you consider how successful his sons were later on in life, tragedy aside.

In later posts, we'll discuss the east coast more and just what makes it the preppy bastian that it is.  The private schools, the colleges, the vacation spots, the styles, and just about everything in between.   The east coast really does have it all, and if you keep reading, you'll see.