Aritzia tee and cardigan  |  Gap denim  |  Sneakers c/o Unnown Footwear  |  Quay sunglasses

Boston's Beacon Hill neighborhood is one of the most photogenic in America. Cobblestones and brick, black shutters and red doors. I think I picked out twelve or more houses I could see myself living in. Although I didn't know it was going to be so hot, I was still happy to be in a comfortable, loungewear-inspired outfit strolling the city streets in search of historical sites. It didn't take long to find some—Boston is just brimming with them.