It is always fun to take in a town’s whimsical festivities and quirks. In Annapolis, Maryland, one such oddball tradition spans three decades of sportsmanship rivaly: between the brass shining, honor loving, All-American Midshipmen from the prestigious U.S. Naval Academy, and a group of snotty rich kids high on marijuana or dad’s card spending limit from some small, hipster friendly LAC called St. Johns College…(anyone who goes or went there- I kid I kid!) Once a year, these two starkly contrasting paths of student body intertwine for a friendly Spring match that gives the whole town an excuse to cosplay in a real life production of The Great Gatsby.
Annapolis is already one of the most traddiest places around as it is. “Mid-Atlantic Trad” as some of our AAAC peers call it; not quite New English WASP, but definitely not quite Southern Prep either. Given by the fact that Annapolis is widely known as the sailing capital of the nation, as host to the oldest and largest seaside promenade and residence to the Sailing Hall of Fame, in addition to the needlesstosay awesome dignity of being the placeholder to the Academy; the town’s seat along the Chesapeake Bay is compounded by the vicinity to the greater DC/NOVA and Maryland neighborhoods.
Successful government, law, and consulting officials and professionals make this area their home, and send their kids in droves to the plenty of local preparatory schools that still carry the doctrine of blazer, tie, and chinos. Higher education is represented by the likes of Georgetown, Johns Hopkins, and Loyola. Nearby Baltimore was once a notable mini-focal point in American menswear too, as hometown to Jos A. Bank starting in 1905 (long before they became a forgettable mall brand surviving off cheap quality and extreme discount techniques). JAB used to make some of it’s Made in USA suits here, while Porn Store Legend Eddie Jacobs carries forth the tradly spirit to loyal patrons. Techprep outfitter UnderArmour and relating prep sport favorite Lax reigns supreme with US Lacrosse headquarters and Hall of Fame on Hopkins campus grounds, and several other nearby collegiate powerhouses supporting this ultimate fratty hobby. Nautical fashion is strong in The Baltimore Look for obvious reasons, seen from the array of embroided critters, madras, and nanny reds. I kind of have a feeling that Bradley Cooper’s character, the unsurprisingly douchey antagonist in The Wedding Crashers, embodies The Baltimore Look. So maybe it is easier to understand why Annapolis, just a short drive away from all of these gold reserves, becomes a summertime playground of cobblestone streets and dockside walks for Washingtonian wealthy elites. Where else should they quench their blue crab cravings and boating enthusiasm?
Crabcakes and Football…
I visited Annapolis years ago on a family road trip up the 95 corridor. We did the sight seeing thing and walked the Naval Academy’s hallowed grounds. We watched all of the young new Plebes marching up and down the Yard in formation in humid summer heat, as we fat lazy tourists in denim shorts and XXL tees with “I love Maryland” graphics watched and snapped pictures comfortably in the tree shade. I remember the sight of huge expensive yachts at port and the aroma of the salty Atlantic. I remember dashing young sailors in their warm weather whites, escorting their visiting proud parents around town. Very cool sight to see and certainly made me wish I could earn a spot amongst the ranks. There were numerous quaint shops and restaurants, and while my father and I paroozed around a shoe store specializing in nautical footwear, we were introduced to Dubarry of Ireland, which is a step above in exclusivity from his second pair of Sperry Topsiders my pops was just fitting on.
Established in 1784 (ironically predating the 1845 founding of the Academy), St. Johns College is a literal stone’s throw away from the Naval garrison walls. I actually don’t remember much about the school since we did not tour there, but from what I gather, St. Johns does attract a vocal minority of traditional preppies like you and me. They arrive from boarding schools farther up north and are sons and daughters of senior government aides and DC law firm partners (okay, maybe also like you but definitely unlike me). There is no formal greek system or varsity athletics program here, so they can be seen going to intramural row practice or strolling to downtown bars in colorful pants instead of tailgating in gold button blazers. Then there is the majority of the heavily progressive student population, who may enjoy such splendid antics like going barefoot, talking about Keynesian economical philosophy, and updating their hundreds of fellow TwitterTwats about the social justice rally tonight. Oh…they’re children of wealthy attorneys and consultants too…they’re just not as prone to following Dad’s path of white collar order: “Be a free thinker, you sheep!”
But one thing the College can be proud of is its success of their “Johnnies” in the noble game of Croquet. Nationally ranked (amongst nine currently active clubs…) St. Johns has a bone to pick with those establishment drones just down the hill, and face each other off in an annual Spring Fling aptly named Croquet Weekend. This is when an eager mob of coeds, sailors, and townies all put in extra effort in celebrating the cheery merriment surrounding the friendly match between the Middies and the Johnnies. Kind of like the Kentucky Derby on an overdose of eccentric steroids, many take advantage of the occasion to complimock (yup just made that up, feel free to use) the pompous genetic makeup innate to the king of country club pastimes, and will adorn old timey boater hats and grow out handlebar mustaches like they are background extras on film set of The Great Gatsby, while others will go for the typical fratdaddy ensemble in their loudest clothing that practically yell out GoToHell.
Here is just a taste of what you will see if you ever find yourself in a Maryland coastal prep mecca.
Mids always dresse in their classic uniforms. Very old school with the patch and cardigan. But unlike the sport inspired collections in Ralph Lauren’s Rugby and Polo, these gameday attire garner truly authentic appraisal.
Each mallet given a nickname
The Fightin’ Johnnies on the other hand prefer themed costumes. This year, it was Animal Housegreekgasmic toga. Notice the Midshipmen can manipulate dress code and accessorize with their own individual marks of preppy undertone.
Naval Tradition meets Urban Prep
Class rings are seen on the 63rd floor Boardroom overlooking the Hudson and on the Nimitz-Class Bridge alike…both where wars are won. Alumni from service academies especially love to, and should, proudly show off their alma mater (the practice itself originated from a certain mortal rival living up at Westpoint.) Case in point: Francis Underwood and his infamous “The Sentinel” (aka The Citadel) class ring. It is said that if you are in uniform at The Pentagon then you should be able to recognize each branch’s insignia from across the briefing table.
An occasion for peacocking. For men and women
Beautiful hats, beautiful smiles
Faded pastels, bowties, OCBDs and sportcoats, pleats for the good ol’ southerner
Bohemians coming out to play
The Most Interesting Man in the World’s older and WASPier brother. Newsboy cap, straw fedora, toast in hand
Glamorous 1920s meets Wholesome1950s meets Chic 2010s
What I like the most about the scenery is not only the palpable sense of enjoyment, but the fact that the pictures above spotlights the resulting benefit from collected groupthink agreement, which says that its okay to chase after your more outlandish sartorial pursuits every once in a while. It takes a lot of confidence to wear some of these outfits by yourself, but given the right kind of festive atmosphere and crowd tendencies (exactly like a preppy sporting outing via a real life damn Croquet Match), it is much easier to have fun with the opportunity and take risks that you’d normally not have the same level of courage to take in regular circumstances. Not saying I would advocate those 1920s hipster throwbacks or that every one of those outfits are something I’d put together for myself… although many of them did look ballin’… but I am just relating to how you would feel less self-conscious in bright yellow critter pants and a plaid bowtie in Annapolis on this particular weekend than you would at a EDM concert in Sacramento. Like-minded people gathering in a like-minded town. Because I do sometimes want to dress outrageously preppy, or provide my take of how a gentleman from the roaring ’20s would splendidly look as in the spirit of Leo, or whatever, without looking too out of place in the boring backdrop of jeans and flip flops to a similar grand event. There are fewer and fewer strongholds in existence where trad and prep are still accepted or even encouraged. You and I and everyone who attended that weekend nod in agreement. But the harsh reality is that the great rest of the brainless masses gawk in disgust. I just wish it could be as free and non-judgmental, as it is in these photo sets, everywhere and all the time.