Walking the Walking City

· What to wear in Boston, Massachusetts ·

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Boston’s Public Gardens

With so many students, Boston is pretty laid back sartorially. A few years back, the standard uniform of college girls was leggings, a North Face fleece, Hunter boots and a Longchamp bag. You couldn’t go anywhere without seeing someone wearing this, and most of the time they came in twos and threes. I can imagine that Boston’s style has evolved a bit, but I would also imagine that it hasn’t strayed too far from this comfortable, functional look.

Of course, you’ll want to look a bit smarter. Despite the ideas of Ivy League academia and Old World elegance Boston may inspire, as the above illustrates, it’s a pretty laid back place. Not only that, but you’ll do a lot of walking (as Boston IS the walking city), so comfortable shoes are key. Here are best suggestions so you blend in like a local!

The Dress

Via Kiel James Patrick

New England natives Kiel James Patrick and Sarah Vickers started Kiel James Patrick with just an anchor bracelet. They’ve grown their brand and (relatively) recently transitioned into apparel. This flannel dress is the perfect this for Boston and you can wear it with or without tights depending on the weather. In autumn, pretty much anything you might wear apple picking will work in Boston and this dress is perfect for those who prefer dresses to jeans. You get the flannel, but you get it in a super flattering dress! Who could ask for more?

The Boots

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Via The Frye Company

Walking around Boston, you’re bound to see plenty of riding boots. Maybe everyone’s channeling their inner Paul Revere. More likely, it’s a legacy of Boston’s preppy scene. Riding boots are comfortable for walking, warm if they need to be, and, of course, beautiful. Especially these ones from Frye. Put them on your wishlist now!

The Coat

Via Boden

The weather in Boston is unpredictable. Especially in the transition seasons. It could be 65 degrees one day then snowing on Halloween (this happened in 2011). Most likely, you’ll have to contend with rain, so packing a waterproof coat is essential. This cute raincoat from Boden channels Boston’s academic reputation while power-clashing patterns with the dress give you a bit of an edge on all the students.

The Scarf

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Pull everything together while also adding a bit of warmth on those colder days, this reversible scarf is the finishing touch. Pulling in the colors from the flannel’s patterns, as well as those in the tweed of the coat, it brings the power-clashing to the next level.

The Bag

Via The Cambridge Satchel Company

Add an homage to Harvard’s hometown’s namesake with this saddle bag from The Cambridge Satchel Company. The navy and blue pull in colors from both the dress and the coat while it adds a bit more of that prep that Boston is associated with. Like the two Cambridges, you’ll see many place-names that have been directly taken from ones in England – it is called New England for a reason!


As long as you’re laid back with comfortable shoes, you can’t go wrong in Beantown. Just don’t forget to add the most important accessory – a cup of Dunkin’ Donuts coffee!

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