Fall in Boston is truly one of the most stylish seasons, and there’s no better way to experience the city’s timeless charm than in effortless, chic outfits paired with unforgettable experiences. From cozy cashmere layers to sophisticated city strolls, this post offers 7 head-to-toe looks perfect for exploring Boston’s cobblestone streets in style. Fall outfit, fall fashion, fall look LTKOver40 LTKTravel LTKStyleTip

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Plaid Barn Jacket | Gap (US)
Winetasting Ella Sweater Blouse | Tuckernuck (US)
Chocolate Suede Buckle Nina Flats | Tuckernuck (US)
Winetasting Vegan Suede Ashford Pants | Tuckernuck (US)
PASCAL | 18K Titanium + Champagne + Rue Tortoise Polarized | KREWE Eyewear
Intrecciato leather pouch | NET-A-PORTER (US)
Solitaire Studs | Shopbop
Cendré Kelly Rectangle Watch | Anthropologie (US)