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 looks, fall fashion LTKTravel LTKStyleTip LTKOver40

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AllSaints Rayanna Pleated Cap Sleeve Dress | Nordstrom | Nordstrom
Zubi Black Suede | Tony Bianco US
Winetasting Ella Sweater Blouse | Tuckernuck (US)
Chocolate Suede Buckle Nina Flats | Tuckernuck (US)
Small Airplane Tote by Hat Attack | Banana Republic (US)
Glass stone drop earrings | J. Crew US
Single Breasted Topcoat In Leopard Print | Shopbop
Solitaire Studs | Shopbop
Intrecciato leather pouch | NET-A-PORTER (US)
Schoolboy Plaid Dickey Jacket | Veronica Beard
Classic belt in croc-embossed leather | J. Crew US
Cotton Oxford Long Sleeve Button Down Shirt | Shopbop
GG1984SK Sunglasses | Shopbop
Estelle Ankle Boots | Shopbop
The Soglio Dress | Shopbop
Vancouver Clutch Handbag | Shopbop
Noir Cashmere Blanket Scarf | Tuckernuck (US)
PASCAL | 18K Titanium + Champagne + Rue Tortoise Polarized | KREWE Eyewear
Cendré Kelly Rectangle Watch | Anthropologie (US)
Wally Boots | Shopbop
Baroque Floral Silk Cashmere Blend Large Scarf | Tuckernuck (US)
WAVY METAL BRACELET | Zara US
Plaid Barn Jacket | Gap (US)
Winetasting Ella Sweater Blouse | Tuckernuck (US)
Winetasting Vegan Suede Ashford Pants | Tuckernuck (US)
THE PAOLA COAT | Favorite Daughter
Chocolate Cashmere Bodie Boyfriend Crewneck | Tuckernuck (US)
Chocolate Cashmere Jane Pant | Tuckernuck (US)
Penrose Sneakers | Shopbop