Boston is a city that’s full of surprises. History lovers can enjoy traversing the cobblestone streets of North End and touring the modern masterpieces at the Institute of Contemporary Art. Meanwhile, fashion enthusiasts will find plenty of shopping options at Seaport, where brands like Everlane and Grace Loves Lace meet local favorites at The Current, home to an always-evolving lineup of lifestyle brands.
“Boston gets a bad rep for having bad fashion, but I don’t think that’s the truth,” says Alison Barnard O’Brien, founder and owner of the Boston boutique Injeanius. Having been on the frontlines of Boston fashion for nearly two decades, O’Brien has seen trends come and go. What really matters to most Bostonians in relation to their personal style can be boiled down to a few key questions, she explains.
“There’s so many people dressing on-trend and they’re thinking, ‘Is it winter-proof? Is it accessible? Can it take my everyday and step it up?'” O’Brien says. “You can be in your denim, but you add those personal pieces that help elevate it.”
One non-negotiable item that should be part of your Boston packing list: a hat. This is especially true if you’re visiting during wintertime. “You need a good hat, whether it’s a beanie or something else,” O’Brien says. “You’ve gotta cover up the noggin.”
And don’t forget the proper outerwear. When those blistering Boston winds hit your body, you’ll want to have every inch protected from the elements.
“You need a coat that covers your bum,” O’Brien says. “The covering of the bum is very important in keeping you warm around here. I also firmly believe in some cashmere – cashmere gets me through our winters.”
Reference the agenda ahead for what to wear and what to do in Boston.

Related:

What to Pack For a Trip to Aspen, From Puffer Coats to Snow Pants Read More POPSUGAR Fashion