If Boston Is the Walking City, You’re Going to Need Some Comfortable Shoes

The weather is beautiful and the city of Boston lies before you, ready to be explored. Known affectionately as the Walking City because of the close proximity of its neighborhoods from the North End to the Waterfront to Faneuil Hall and beyond, Boston is best seen by foot. And with the old cobblestones and uneven bricks that make up many of the walkways throughout the city, you are going to need some comfy shoes. Stilletos and this city do not generally mix, unless you are being chauffeured or doing it up valet style.

And despite GQ’s recent rating of Boston as the #1 Worst-Dressed City (yes, we are still feeling offended, despite the fact that GQ is out of fashion itself) you need to look good while remaining comfy. My suggestion? Go for a home grown favorite that just may surprise you with their super stylish looks for men and women, while providing comfort that just may out-do your expensive workout sneakers.


Rockport was long known as the sensible shoe source in the footwear world. Remarkably comfortable, but perhaps not runway ready. Today, that is clearly not the case. Head into their boutique-like concept store at 215 Newbury Street, and you may find the need to step outside again to make sure you are really in a Rockport shoe store as I did. Alas, indeed it is!

Generally not a big fan of men’s shoes, I felt myself drawn to them immediately. So many hot styles! From a Londoners buckled work boot look to a slick business casual ready loafer, these are shoes that would make a woman want to date a man.

But, I clearly could not resist the women’s selection for long. Where to go first with the fall styles ready to be rung up. The stunningly tall Luciana Corset boots to the anklet styles harkening back to the roaring 20’s, and the Janae Pumps, a new take on the classic pump (with heels ample enough to handle Boston’s sometimes rugged terrain). For the first time – I wouldn’t have to decide between stylish and sensible – I could have both. That is truly remarkable in any corner of women’s fashion.

So where would your Rockports take you? Would you finally walk the red line of the Freedom Trail, go on a culinary tour of the South End or are you more the dancing shoes kind of person?

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