My Kinda Clothes: Annapolitan Trad


I’m pretty confident that my personal style reflects, at least in part, a subset of Eastern dress that could be called Annapolitan Trad. It’s not thrifty, scratchy-wool, down-east Yankee. It’s not pressed khakis and bow-tie ACC tailgating, either. And it’s certainly not Upper East Side Belgian shoes or Prince Albert slippers. But, like those styles, it is very much of its place.

Annapolitan Trad is a bit rumpled and old school, but not self-consciously so. It’s conservative — plain, even. Money doesn’t flaunt itself (much), least of all because you’re never going to trump the Midshipmen walking around town in their dress whites. It’s old — the city was temporarily the capitol of the nation in the late 18th century, and General Washington resigned his commission here  — and it’s small. But most of all I think Annapolitan Trad reflects the outdoors and Chesapeake Bay.

So here are my kinda clothes.


Khakis, OCBDs & Madras

Never jeans and never point collars, unless you didn’t change after you got home from your job inside the Beltway. The yellow Duck Head label was a calling card, and you can identify your peers because wrinkled candy-stripe oxfords remain firmly tucked in with an old red/blue or yellow/blue surcingle belt. Summertime is for both short and long-sleeved madras shirts (a little faded, sometimes pressed). Khakis are either: a) cuffed and short because they’ve shrunk after 10 years of laundering; or b) long because you let the cuff out (due to aforesaid shrinkage), but can still see the crease where the cuff used to be. Loud colors, Nantucket Reds (faux or real), and Vineyard Vines are really only for high school lacrosse-playing bros.


Boat Shoes, Penny Loafers & Longwings

Not accessories for landlocked frat brothers, but shoes worn by people who actually spend time on boats. I have a pair of technical shoes for Friday night racing that nobody would ever call trad (Sperry Sea Kites), but I also have a well-worn pair of Sebago Clove Hitch moccasins. Loafers are either black or oxblood, and either plain or beef roll. No tassels, no socks. Unless you’re going to be in court or in DC, in which case it’s longwings (not wingtips), and only in traditional colors, please. No light tan, etc.


Jos. A. Bank

There’s just no way around it: recent cringe-worthy changes notwithstanding, if you’re an adult professional man in Maryland, you have a Joe Bank suit (or six) in your closet. If you don’t, you’re not really from here. The company was born in Baltimore, and is still technically headquartered in Carroll County. Khaki, olive and navy poplin (one of each) for summer; assorted grey and blue wool for the rest of the year.

bank suit

Sailing, Hunting And Fishing

They say Annapolis is a drinking town with a sailing problem: everybody here either races, cruises or just mixes Dark & Stormies for the rest of the crew. And when we’re not sailing, we’re fishing. Then, when the weather gets cool, we go waterfowling. Raingear does double duty between sail and power.

Eddie Bauer vest

LL Bean boots actually go into the turkey woods and the duck blind. Like many, my hall closet reflects an Eastern Shore influence because its where my waders and camo hang. Costas probably edge out Ray Ban aviators, but neither are worn without croakies: you don’t want to lose your eye protection when you’re leaning over the gunwale. — PAUL DOUGHERTY


17 Comments on "My Kinda Clothes: Annapolitan Trad"

  1. Great piece and lots of overlap with other varieties of Mid-Atlantic and New England Ivy.

    “There’s just no way around it: recent cringe-worthy changes notwithstanding…”

    Well, there is a way around it, but a fellow–the sort who’s smitten with a certain interpretation of “traditional”–has to give more than a damn about sticking with the natural shouldered sack jacket. More than a little effort is required. For a style that’s accessible by lazily placing an order with LL Bean, Lands End, or Brooks, the sack jacket remains the defining idiosyncrasy. Its scarcity only adds to its reputation as a totem of a style that’s gone the way of the dinosaurs (not pejorative). To and among the few who bother to care, it reveals a bit of fidei defensor.

  2. As a lifelong Marylander, I concur with most of this post. The other areas of the state where this all rings true is a swath from central Baltimore (starting near the Johns Hopkins campus) and running north to Towson, Ruxton and up into horse country. You’ll see it in the Montgomery County towns of Bethesda, Chevy Chase and Potomac.

    Non lax brahs wear VV, but of the understated variety.

  3. What’s the make of the vest? Love it.

  4. I’m wearing that madras shirt from O’Connell’s right now. Faded from many dunks in the sink with woolite. My kind of clothes.

  5. @Flo


  6. Angus Sweetwater | July 24, 2016 at 9:36 pm |

    Spot on, I’ve been labeled a disheveled prep for 30 years. From the Land of Pleasant Living.
    RT from Pinehurst/Towson

  7. Charlottesville | July 25, 2016 at 2:37 pm |

    Great job Paul. There are a lot of similarities in our two smallish towns, particularly if you sub in riding for sailing as a sartorial influence. I just wish Jos. A. Bank was still the home of 3/2 sack suits and coats that I remember from the 70s.

  8. @Charlottesville: thanks very much; despite having many friends and family who attended Mr. Jefferson’s University, I’ve actually never been. (most of my days in the Old Dominion were spent in Farmville)

  9. Charlottesville | July 25, 2016 at 5:04 pm |

    Paul — May I assume that you were a Hamden Sydney boy? I spent a few years up the road at W&L, which has (or had) a similar feel. Or perhaps you were visiting the fair sex at Longwood. I have enjoyed my visits to Annapolis. It really is a lovely city.

  10. @Charlottesville: a good high shool friend went to HSC and, as I went to a Jesuit college (where there was Div. I lacrosse, but neither football nor fraternities), road trips to Farmville – and making new friends from Hollins & Sweet Briar – were always fun.

    And if you – or any of CC’s readers – ever find yourself in or near my fair town, please drop me a line through the blog: it’d be my pleasure to buy a round.

  11. T. Bearden | July 25, 2016 at 8:09 pm |

    Marylander here…Eastern Shore/Talbot County. Used to live about 20 minutes from Naptown on Western Shore, and before that, Charm City. Joseph A. Bank? Not for me, thanks. I don’t think the quality was ever very good, even in the ’70s. Can’t imagine what’s is like now (“Buy one suit, get three free!” says the obnoxious radio ad. No kidding.).

  12. NaturalShoulder | July 25, 2016 at 10:11 pm |

    Paul – thank you for taking the time to put together post. I admire your style.

  13. I live in northern Baltimore County (horse country) where I work for a girls boarding school. The independent school scene around Baltimore is the largest per capita in the US, and I think that this had something to do with the development of this particular subset of traditional/prep style. As in most matters regarding this region, Maryland has the odd position culturally of not really being in the North, but not truly in the South, either.

    I agree with most of the finer points above, but not all. I do see plenty of tassel loafers in the prep school circles (on adults, not on students), and virtually no black loafers. Mostly brown with some oxblood.

  14. I realize that Paul was not trying to be encyclopedic, but when it comes to belts, I have to imagine that Annapolis is a hotbed for North Sails belts and all kinds of nautical themed sailing belts. I have rarely met a sailor that did not wear ribbon belts.

  15. @Anonymous: that’s correct – as I alluded to in describing boat shoes – plenty of technical sailing gear (and fishing gear too) creeps into the otherwise-Trad Annapolis wardrobe: a guy on Main Street may be wearing khakis and an OCBD, but with a Quantum Sails web belt, or a Gill pullover.

    If you look closely at my pic, I’m actually wearing a belt with Chesapeake lighthouses embroidered on it: you can see both Thomas Point Light, and Point No Point.

  16. Banks appears to be phasing out its poplin suit line. Unthinkable. I first bought one during my sophomore year at Wofford in the waning days of the Reagan years.

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