Guest blog post from Felicity Leo

What to wear in Europe this fall

Travel isn’t just about the destinations , it’s about how you show up in the world. Whether you’re strolling through the lively Ballarò Market & Vucciria Market in Palermo, or enjoying the best culinary delights across Sicily, your travel style should reflect you.

For women over 50, the ideal travel packing list balances timeless elegance with modern comfort.

The secret?

Confidence-boosting pieces and comfortable travel outfits that work for your lifestyle, body, and the journey ahead!

Effortless Italian style for women over 50

Italian women are known for their chic, polished, effortless yet refined look. When you're planning a trip to Italy or other parts of Europe this fall, it’s ideal to build a travel capsule wardrobe inspired by their timeless aesthetic. Start with high-quality staples that can be dressed up or down, like a well-fitted blazer, a classic trench coat, and a pair of stylish yet comfortable trousers and for overall travel a microlight down jacket can easily be packed away for cool days.

Stick to a timeless color palette like Navy + White + Camel or Black + Olive + Ivory for easy mixing and matching. These versatile tones create stylish looks that keep your suitcase light while offering endless options.

Choose natural, breathable fabrics like cotton, silk, and lightweight wool for both beauty and function. And remember: layering is essential for Italy’s shifting fall weather - think scarves, cardigans, and leggings to move comfortably from chilly mornings to warm afternoons.

Comfortable yet stylish footwear for Europe in the fall

Comfortable walking shoes are an absolute must! The best shoes that combine function and fashion are leather ankle boots, supportive sneakers, or water-resistant loafers that keep you cozy and chic through fluctuating fall weather.

Especially for cobblestone streets, hilly towns, and long sightseeing days - prioritize shoes that have arch support, cushioned soles, and non-slip traction.

Brands like Vionic, Elena Mirò and Marina Rinaldi offer amazing options for women over 50. You'll need stylish yet supportive shoes that can handle long days and your feet will thank you!

Accessorize with purpose, elevate every look, effortlessly

Accessories can completely transform your travel outfits.

Thoughtful accessories allow you to express your personal style and adapt effortlessly to different occasions throughout your travels.

A statement necklace or an elegant watch bring freshness and personality to your travel wardrobe without overpacking. For those crisp fall days, a structured hat or sleek leather jacket can also instantly elevate your look, while offering practical warmth and a touch of sophistication.

To keep your essentials secure (and make room for a few shopping treasures), go for a secure crossbody bag or a stylish backpack making fashion functional.

Embrace your personal style in comfort and chic confidence

Fall in Europe is all about crisp air, golden light, and timeless fashion, so your travel wardrobe should reflect that.

Remember to focus on pieces that highlight your personality and work with the changing temperatures.

If you feel your best in structured trousers and a soft knit sweater, pack them! If a tailored coat with ankle boots gives you that stylish edge, make it your signature look.

The most fashionable travelers are the ones who own their personal style, not the ones chasing trends.

Ready to travel in style?

Join other like-minded women on a curated adventure through Italy’s most flavorful season. Explore the Fall 2025 Women's Group Trip to Sicily with Olegana Travel Boutique — space is limited and this one-of-a-kind journey is filling fast!