What to Wear in Boston

Boston is a city full of surprises. History buffs can enjoy traversing the cobbled streets of the North End and visiting modern masterpieces at the Institute of Contemporary Art. Meanwhile, fashion fans will find plenty of shopping options at Seaportswhere brands like Everlane and Grace Loves Lace meet local favorites at Nowhome to an ever-expanding lineup of lifestyle brands.

“Boston gets a bad reputation for bad fashion, but I don’t think that’s true,” says Alison Barnard O’Brien, founder and owner of the Boston boutique. Injeanius. Having been at the forefront of Boston fashion for nearly two decades, O’Brien has seen trends come and go. What is it right the problems for most Bostonians in terms of their personal style can be boiled down to a few key questions, he explains.

“There are so many people who dress on trend and they think, ‘Is this winter proof? Is it accessible? Can I wear it every day and upgrade it?'” says O’Brien. “You can wear denim, but you add personal pieces that help lift it.”

One non-negotiable item that should be part of your Boston packing list: a hat. This is especially true if you are visiting during winter. “You need a good hat, whether it’s a beanie or something else,” says O’Brien. “You should cover the noggin.”

And don’t forget the right outerwear. When the scorching Boston winds pound your body, you’ll want every inch protected from the elements.

“You need a coat that covers your bottom,” says O’Brien. “Covering the butt is so important for keeping you warm around here. I’m also a big believer in cashmere cashmere getting me through our winters.”

Refer to the agenda ahead for what to wear and what to do in Boston.