Like most bicycle-riding, mass-transit-commuting, non-profit-working 20-somethings living in an urban center, I wish I made more money. I’d buy nicer, newer clothes and rent a bigger apartment with fewer roommates. I’d also spend more of my time (and money) at the baronial joints in town.
Unlike my hipster brethren, I’m not quite at home in dive bars and sweaty clubs. Never have been. My preference is for a gentleman’s lounge (in the true sense of the term). Paintings of red-coated Englishmen on horseback in a field with their loyal basset hounds hot on a trail. That’s my scene.
Blame it on my roots. My parents are country-clubbers: I grew up on the golf course and in the club house, getting my Sunday brunch served to me with a “Yes, sir” (and a generous helping of adolescent white guilt). I also hail from Kentucky – land of hundred-acre horse farms, mint juleps, and on every first Saturday in May, beautiful women don sundresses, pearls, and Derby hats. (There’s a horse race, too.) The whole affair informed my sense of style, the type of woman I’m attracted to, and my definition of a good time on the weekend. Unfortunately, I also make around 30Gs a year.
I have learned to cope. I rock penny loafers like any proper gentleman –mine just happen to be the $16.99 pair from Payless. I get my navy blazers off the sales rack at Macy’s, my seersucker sans-irony at Urban Outfitters. On sunny Sunday afternoons, I rent a Zipcar and head north to Ipswich to take in the polo matches – a straw picnic basket, quilt*, and bottle of Trader Joe’s three buck Chuck in the back seat.
Here’s what else I do: I pick my spots. If you’re going to emulate the landed gentry, you have to find the right heres-and-theres in which to get your rich on. It’s not a matter of ‘staying classy’ but doing classy wherever you can – ie, eating store-bought tortellini all week so you can drop twenty bucks on a champagne cocktail without batting an eye.
And in Boston (the epicenter of America’s ‘old and moneyed’), there are more than enough places to buy that twenty-dollar champagne cocktail. As long as your drink comes with the right set of circumstances—under the dim lighting of a chandelier, in the comfort of an overstuffed, gold-studded couch, beneath the gaze of a deer bust—the money you drop on it won’t really matter.
Without further ado, here's where to class it up in Boston:
Scollay Square 
21 Beacon St, #1
At the peak of Beacon Hill, across the street from the Boston Athenaeum**, and three doors down from the capitol building, Scollay Square buzzes with political gossip generated by a swarm of WASPs. The bar wraps from the front door all the way to the rear, where shelves of wine climb the wall. The ceilings and windows are suitably enormous. There’s a kitsch factor as well: black-and-white pre-war era photographs of the square line the ceiling’s perimeter. Stay in the restaurant area and you’ll see pictures of old politicians; hobnob your way to the back, though, and you’ll find four photos of 1940s blonde beauties that are viewable only by looking up into the reflection of the bar’s mirror.
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No. 9 Park
9 Park St
No. 9 Park has the (well-earned, though overstated) reputation as the best restaurant in Boston, which is reason enough to include it on any classy jaunt through town. It too is doors away from the capitol – on the bottom floor at 9 Park Street (obviously). The décor is a touch modern and sparse for my traditionalist tastes, and the staff, though capable, wasn’t what one would call truly classy. (Our waiter gaffed, referring to my drink as “The Moulin Rouge.” I had, in fact, ordered “Le Morne Rouge.”) Still, the youngish, well-dressed, good-looking clientele had me suspecting there might be other undercover plebes-in-prince’s clothing mingling about. And on the way out, the maitre d’ holds the door for the lady while offering a handshake to the gentleman, an undeniable high-brow touch sure to put a hop in one’s step.
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Locke-Ober
3 Winter Pl
Locke-Ober puts blue in the blood of any patron. Audis and Mercedes line up outside. Basset hound paintings decorate on the walls. Thousand-dollar bottles of wine rest on white tablecloths. An all-male wait staff in bowties zip through a flock of silver-haired gentlemen who swill martinis and guffaw about the halcyon days of trickle-down economics. Be forewarned, though: your liberal guilt might flair up something terrible. Locke-Ober rocks ‘old moneyed’ Boston a little too well: it’s run by an all-immigrant wait staff, and watching them cater to rich old white folk reminds why you escaped from your parents’ country club in the first place.
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The Oak Room
138 St. James Pl
The name is self-referential: it’s one giant, square, oak room in Copley Square. Oak Room hosts a live jazz band six days a week. Your best bet is to have a few drinks before going, as the 20-page, leather-bound cocktail menu and dim table lamps don’t facilitate reading fine print (unless you brought your monocle). A couple martinis will also keeping you from remembering that you’re actually mingling at the Fairmont Hotel, and that the entire staff is wearing nametags, and that the building connected to this beautiful den evokes less “Mahler” and more “ mall.” Keep your line of vision pointed toward the band and the giant windows that look out over the square at the city’s public library.
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The Parker House
60 School St
This has become my classy home away from home. Like a highly-paid nanny or an expert masseuse, Parker House comforts and soothes me in a way that the other gentlemanly quarters do not. Maybe that’s because, like me, the Parker House is a fraud; and a fraud can spot a fellow fraud from a mile away. Notice, for instance, the tourists with their luggage rollers and shopping bags fresh from Faneuil Hall; or the way everything in the lobby feels like it’s been brushed by a one-karat Midas touch. They’ve put the Kennedy name on just about anything that can be named (the lobster roll, the conference room, etc.), which, quite frankly, is the oldest Boston tourist trap trick in the book. And as for why the pastrami sandwich is named after Malcolm X, I have no effing clue. But still…but still. The Parker House can’t help but charm with its nouveau richesse. Take a seat in the bar, and you’ll be served a warm bowl of mixed nuts. Finish half of it, and they’ll swap you for a new bowl before you even notice. Chandeliers. Dark carpeting. A cocktail menu with extravagantly named, overpriced drinks. Maybe it’s all a show, and maybe behind all those curtains, it’s a pretty average bar. But the Parker has a lot of curtains – enough to get lost in and enough not to be able to see past if you don’t want to. Plus, when you’re putting up your own curtains for an evening, that can be exactly the thing you’re looking for.
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*Known as an ‘heirloom’ among the genteel
**That’s ‘library’ to the blue collar.