Is Boston the worst city in America?

This is a guest post from Anne Weiskopf.

Within a two week span this summer, Boston was honored by GQ Magazine as being first in “The 40 Worst-Dressed Cities in America” and by two Michigan psychiatrists as “The Least Friendly City” in the country. So, what’s up Boston? And, is it causal?

Boston skylineLet me start by saying that having excellent sports teams is one of the greatest things about Boston. The downside is that a large swath of the male population does not seem to comprehend that what one wears to see the Red Sox, Celtics and Patriots (hats, tee-shirts with stains, shorts, and sneakers with white socks) is not acceptable couture for other occasions. As GQ humorously summarized, Boston is a “Jurassic Park for fashion troglodytes.”

But what about the “least friendly” designation? Mayor Menino, for one, disagrees: “I go to all the events in the city of Boston. People say, ‘gee what a friendly city.’ Ask the cab drivers. They think we have a friendly city also. I don’t know who did this poll. I never heard of it. It’s one of those polls that some people I don’t think there’s
any credibility in it at all.”

Others agreed with the mayor, including Ayla Rosen, a Merchandising Major at Marist College and summer intern at Bostinnovation. In her blog post
Last Week it was Worst Dressed, Now Boston Ranked the Least Friendly City in America, she notes: “Just like the lovely people at GQ, the people filling out the survey might just be jealous that they do not live in Boston. If they think people from Boston they should think about getting out more and perhaps paying a visit to GQ in New York to learn about what it means to be unfriendly.”

Still others mentioned the history of discrimination in Boston as a cause for the “Least Friendly” accommodation.

Having grown up in Westchester NY, and having lived here for more than 30 years, I understand the perception that Boston is unfriendly. The truth is that Boston is both tribal (I think this sums it up much more accurately then ‘discriminatory’ does) and much more conservative and cautious then NYC. It can take years to meet your neighbors, but, once you do – they’ve got your back. And, if you’ve ever driven in Boston, you’ll know that Boston drivers don’t give you the warm and fuzzies.

So – can being the ‘worst dressed’ city actually result in Boston being the ‘least friendly’ too? Perhaps. As I identified in my 5th grade paper on what kind of mother I wanted to be “Looking nice helps because people are more likely to be attracted to nice, neat looking people. Then if you have a nice personality, they will like you. They probably wouldn’t have found out if you didn’t look nice.”

There you go Boston, words of wisdom from an 11 year old New Yorker. And Boston, as badly dressed and unfriendly as you may be, you’re still my home, and the rest of you are just plain jealous!


Anne Weiskopf lives in the Boston area, and has spent many years in the tech media and B2B market. She provides sales and business development services to agencies and companies who are utilizing social media strategies and tools, and will be launching a blog called “Rip Off The Roof” in the near future.
You can find her on Twitter @AnneWeiskopf 

Image – freefotouk

13 Responses to Is Boston the worst city in America?
  1. AnneWeiskopf
    August 24, 2011 | 8:20 am

    @lizscherer thanks darling. and you to @jeffespo 🙂

  2. AnneWeiskopf
    August 24, 2011 | 8:53 am

    @karenmcp Thanks so much Karen; much appreciated, esp coming from you. xo

  3. inthekisser
    August 24, 2011 | 9:41 am

    @jeffespo according to @Gawker, #Boston is one of the least-worst 🙂 and they’re from NY! @anneweiskopf

  4. AnneWeiskopf
    August 25, 2011 | 10:10 am

    @eric_andersen Thanks Eric! (I only refute Boston have badly dressed women 🙂 xo

  5. eric_andersen
    August 25, 2011 | 10:14 am

    @AnneWeiskopf oh that’s true 🙂 But put aside the sports dressing and I think you can refute, besides all cities have this contingent

  6. AnneWeiskopf
    August 25, 2011 | 10:19 am

    @eric_andersen yup. I’ve been in more then one fashion apocalyptic city for sure.

  7. AnneWeiskopf
    August 25, 2011 | 10:19 am

    @eric_andersen yup. I’ve been in more then one fashion apocalyptic city for sure.

  8. AnneWeiskopf
    August 25, 2011 | 10:29 am

    @PattieSimone Thanks for the RT!

  9. PattieSimone
    August 25, 2011 | 3:17 pm

    @anneweiskopf You’re welcome Anne! Hope all is well up in Boston 🙂

  10. schneidermike
    October 4, 2011 | 6:12 pm

    @jeffespo if we did a marketing campaign that showed how truly awesome Boston is, we’d never move an inch on 128 or 93

  11. jeffespo
    October 4, 2011 | 9:10 pm

    @schneidermike agreed how goes it by you

  12. eloCnitsuJ
    October 19, 2011 | 6:48 pm

    @jeffespo Yes.

  13. frankmarketing
    November 5, 2011 | 8:31 am

    @jeffespo Not sure about Boston. My vote goes to #Kansas City for having the nicest people.