Planning a trip to Italy this fall? Let’s make outfit planning effortless. These looks are curated with user experience in mind—easy to layer, comfy for all-day wear, and chic enough for every photo op.
We’ve designed this guide to help you scroll, decide, and pack without overwhelm. Clear tips, stylish picks, no fluff.
Chic Gondola Look with Tweed and Luxe Accessories
This high-fashion mix of houndstooth, leather boots, and a quilted Chanel bag is a standout style for scenic canals and photo ops in Venice.
✨ Get the Look
🧥 Oversized Houndstooth Coat / 👕 Black Turtleneck / 👖 Pinstripe Trousers / 👜 Quilted Chanel Handbag / 👢 Black Leather Combat Boots / 🕶️ Tinted Sunglasses / 💍 Statement Earrings
Effortless Roman Style
This look pairs classic denim with a sleek black leather jacket, perfect for exploring Rome with a modern edge.
✨ Get the Look:
🧥 Black Leather Jacket / 👕 Black Top long Sleeve / 👖 Mid-Wash Jeans / 👜 Black Bag / Brown Bag
Layered Tweed and Mini Dress Combo for Fall Cafés in Italy
A textured plaid coat layered over a belted mini dress and tights is the ultimate chic-meets-cozy look for November café outings.
✨ Get the Look:
🧥 Plaid Tweed Coat / 👗 Textured Mini Dress / 👜 Black Bag / 🧦 Sheer Black Tights / 👢 Black Suede Ankle Boots
Casual-Chic Trench Outfit for Fall in Italy
A lightweight beige trench over denim and knits offers effortless layers for warm afternoons and crisp evenings in Tuscany or Rome.
✨ Get the Look
🧥 Beige Trench Coat / 👕 Ribbed Knit Top / 👖 Mid-Wash Straight Jeans / 👜 Cream YSL Crossbody / 🕶️ Classic Aviator Sunglasses
Rustic Romance in Verona
The contrast of a cropped brown jacket and a flowing white dress makes this look both grounded and ethereal.
✨ Get the Look:
🧥 Brown Cropped Jacket / 👗 White Midi Dress / 👜 Quilted Gold Chain Bag / 👢 Beige Heeled Boots
Neutral Knit Dress and Trench Combo for a Roman Afternoon
A soft beige knit dress under a classic trench is the perfect balance of comfort and elegance for tossing coins at the Trevi Fountain.
✨ Get the Look
🧥 Beige Trench Coat / 👗 Ribbed Sweater Dress / 👟 Chic Sneakers / 👜 Floral Crossbody Bag / 🕶️ Round Sunglasses
Tuscan Layers
This elevated all-black outfit keeps things warm and refined, with a high-neck knit and tailored coat combo.
✨ Get the Look:
🧥 Long Black Coat / 🧶 Black Turtleneck Sweater / 👖 Cream Trousers / 👟 White Sneakers / 👜 Tan Leather Tote / 🕶️ Oversized Sunglasses
Modern Milan Minimalism
A quilted jacket meets crisp whites in this clean and polished look, made for urban walks and aperitivo hours.
✨ Get the Look:
🧥 Brown Quilted Jacket / 👔 White Button-Down Shirt / 👗 White Mini Skirt / 👜 Cream Quilted Bag
Checked Coat and Scarf Layered Look for November Sightseeing in Rome
A tailored plaid coat and striped scarf styled with denim and sneakers is a comfy-cool outfit for fall days in Rome.
✨ Get the Look:
🧥 Checked Long Coat / 🧣 Yellow Striped Scarf / 👖 Cropped Blue Jeans / 👟 Distressed Silver Sneakers
Soft Neutrals, Sharp Pop
Comfy chic meets playful with a cream knit set against bright yellow sneakers — unexpected and stylish.
✨ Get the Look:
🧶 Cream Knit Sweater / 👖 White Cropped Pants / 👟 Yellow Sneakers / 🕶️ Modern Sunglasses
Parisian-Inspired Houndstooth Look for Italy Fall Café Days
A classic houndstooth coat layered over all-black makes this look refined yet cozy for a November coffee stop in Italy.
✨ Get the Look:
🧥 Houndstooth Long Coat / 👗 Black Knit Dress / 🧦 Sheer Tights / 👢 Black Ankle Boots / 👜 Black Chain-Handle Shoulder Bag / 💄 Red Lip
Chic Trench and Printed Scarf Look for Milan Street Style in November
This polished fall outfit features a classic trench, vibrant scarf, and heeled boots—perfect for a stylish stroll through Milan.
✨ Get the Look:
🧥 Camel Trench Coat / 🧣 Multicolor Printed Scarf / 👚 White Top / 👖 Ripped Skinny Jeans / 👢 Cognac Leather Ankle Boots / 👜 Gold Woven Clutch / 🕶️ Round Sunglasses / 💄 Bold Red Lip
Rome Steps Chic
A tailored taupe coat layered with a printed scarf and sleek sneakers balances elegance and comfort—perfect for wandering through ancient ruins and cobblestone streets.
✨ Get the Look:
🧥 Long Taupe Coat / 🧣 Patterned Silk Scarf / 👖 Black Slim Pants / 👟 Grey Sneakers / 👜 Quilted White Shoulder Bag
Roman Coffee Run Vibes
A warm camel coat and black leggings combo makes this outfit the perfect on-the-go look with a stylish twist.
✨ Get the Look:
🧥 Camel Coat / 👕 White Knit Top / 🖤 Black Leggings / 👟 White Sneakers / 👜 Brown Crossbody Bag / 🕶️ Round Sunglasses
ome Fountain Charm
A plaid coat layered over a cream sweater dress and paired with tights brings effortless romance—perfect for wandering Rome and tossing a coin in the Trevi Fountain.
✨ Get the Look:
🧥 Checked Coat / 👗 Cream Sweater Dress / 🧦 Sheer Tights / 👟 White Sneakers / 👜 Mini Top-Handle Bag
Colosseum Glam Early Fall
A tailored cream blazer and high-waisted jeans are effortlessly balanced by a crop top and luxe accessories.
✨ Get the Look:
🧥 Cream Blazer / 👚 Long Sleeve White Crop Top / 👖 High-Waisted Jeans / 👜 Quilted Shoulder Bag / 🕶️ Statement Sunglasses
Denim & Dress Done Right
This effortless combo pairs a crisp white dress with a classic denim jacket, creating a light yet grounded look perfect for sunny fall afternoons in Italy.
✨ Get the Look:
✱ Denim Jacket / ✱ White Maxi Dress / ✱ Cream Crossbody Bag / ✱ Dark Sunglasses / ✱ Gold Watch / ✱ Brown Shoes
Soft Neutrals at the Trevi
A ribbed cardigan tucked into high-waisted trousers brings both warmth and elegance to this relaxed Italian fall look.
✨ Get the Look:
🧶 Cream Knit Cardigan / 👖 High-Waisted Tan Pants / 👜 Structured White Shoulder Bag / 🕶️ Cat-Eye Sunglasses
Timeless in Rome
This look layers a creamy coat over jeans and a knit, giving off that perfect cozy-yet-stylish fall traveler vibe.
✨ Get the Look:
🧥 Beige Wool Coat / 👕 Cream Sweater / 👖 Dark-Wash Jeans / 👟 White Sneakers / 👜 Tan Mini Handbag / 🕶️ Round Sunglasses
Golden Hour in the Eternal City
Snug leggings meet a textured teddy coat in this comfy yet fashion-forward Rome-ready outfit.
✨ Get the Look:
🧥 Beige Teddy Coat / 👚 Black Top / 🖤 Black Leggings / 👟 Chunky White Sneakers / 🕶️ Oversized Sunglasses
Cream on Cream Street Style
This chic layered outfit embraces all-white tonal dressing with a relaxed yet polished silhouette, ideal for city strolls.
✨ Get the Look:
🧥 Long Cream Trench / 🧶 White Knit Turtleneck / 👖 Cream Wide-Leg Trousers / 👟 White Sneakers / 🕶️ Black Cat-Eye Sunglasses
