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Heartbreakingly preppy, Brahmin restaurants?

If you had to list some of Boston's most staid, preppy, conservative, bon vivant-y places -- what might come to mind? Besides Locke-Ober, which seems a bit past its prime.

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  1. Radius and Harvest come to mind.

    3 Replies
    1. re: teezeetoo

      Radius strikes me as more hipster than preppy? Good food, though.

      1. re: nay1028

        Radius, hipster? It's full of suits!

        1. re: Beachowolfe

          perhaps "reminiscent of '80s shoulderpads and cocaine," design-wise? Beverly Hills Cop Goes To Boston?

      1. re: purple bot

        I agree that it fits the bill well. I think it's absolutely terrible and overpriced, but it's preppy.

        1. re: DoubleMan

          I've had nothing but good meals there. But think it was preppier when it was at the Pudding.

          1. re: Splendid Spatula

            I completely agree, Upstairs at the Pudding had a much 'preppier' feel. Upstairs at the Square is more offbeat than anything.

            Pudding was so much better in every way. I really miss that roofftop garden outdoor space.

        2. re: purple bot

          uots may have preppy guests, but the animal print carpet, hot pink and silver foil walls are anything but.

          agree about harvest though.

          will add bar at the boston harbor hotel. crawling with white shoe lawyer-types.

        3. Cafe at theTaj but a martini in the bar might be a better choice.

          Penny
          http://www.bostonzest.com/

          1. what does preppy taste like. never had a button down shirt or penny loafers I didn't like.

            1 Reply
            1. re: treb

              I find the madras at J. Press has the only authentic flavor around here. The Andover Shop's is a little too bland.

            2. Well, the Harvard Club, of course http://www.harvardclub.com

              The Hampshire House, Sunday brunch. http://www.hampshirehouse.com/

              Maybe brunch, anywhere...

              The Sail Loft, which does not seem to maintain a web site (that's bon vivant-ness for you - "we'll get around to it one of these days...

              )

              https://plus.google.com/1149989358013...

              2 Replies
              1. re: latertater

                Second The Sail Loft. Pearls and Twin Sets, khaki pants abound. Actually if you can avoid their annoying bar scene, their fish and chips are pretty good, although their chowder is abysmally thick

                1. re: Wannabfoode

                  The bar scene is full of very young preppies (21-30). I live in the neighborhood and do not eat there; I do not care for deep fried food. It's mainly tourists eating there, and most of them are far from preppy.