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.