What to Wear to a Winery: Elegant Outfits for Tuscan Tastings

Visiting a Tuscan winery is far more than just a wine and food experience — it’s a journey through culture, breathtaking landscapes, and the art of hospitality. Whether it’s a sunset tasting among the vines or an exclusive dinner at a private estate, every occasion calls for an outfit that blends elegance and comfort without sacrificing practicality. For those who want to immerse themselves in the timeless charm of the Florentine hills with impeccable style, choosing the right look is an essential part of the pleasure. Here’s a guide designed for those who appreciate dressing well even while traveling, with a keen eye for setting and authentic Italian flair — especially when wondering what to wear to a winery.

What to Wear to a Winery: Dressing for the Setting

The ideal style for a day at a winery falls somewhere between refined casual and country chic. The relaxed atmosphere invites simplicity, but every detail should still feel intentional. Typically, the dress code depends on the occasion: a casual daytime tasting allows for more laid-back looks, while a vineyard dinner calls for a more polished elegance.

Choosing breathable, lightweight fabrics and reversible leather jackets is key to staying comfortable and graceful in the Tuscan climate. Footwear should be both stylish and practical: opt for flat sandals, or block heels that offer stability on gravel or dirt paths. While all-white outfits may look stunning, they’re not always the most practical choice on dusty or muddy terrain. Instead, consider neutral, earthy tones that blend seamlessly with the landscape. Pair your look with a refined accessory — like one of our summer leather handbags, perfect for countryside elegance.

H2: Vineyard Attire in Tuscany: What to Wear in Italy’s Wine Country

In Tuscany — especially in the countryside surrounding Florence — the vineyard attire experience takes on a distinctly Italian flavor, where style is very much part of the ritual. The most renowned wineries often host exclusive events: lunches among the vines, sunset aperitifs, and vineyard dinners overlooking rows of cypress trees. In these settings, your outfit should reflect understated sophistication.o dive deeper into local style heritage, discover our story in Florence fashion.

Flowy, feminine pieces are always a winning choice: printed midi dresses, silk blouses paired with wide-leg trousers, or linen sets in natural tones like sand, sage, or terracotta. Accessories — handcrafted leather bags, elegant sunglasses, and wide-brim straw hats — complete the look with a timeless sense of charm. It’s not about being showy, but about a thoughtful, effortless elegance that blends seamlessly with the setting.

Can You Wear Jeans to a Winery? Smart Casual vs. Too Casual

While elegance is often associated with dresses and skirts, jeans — when chosen and styled thoughtfully — can also be a sophisticated option for the winery. A pair of dark denim, tailored or cropped, paired with a crisp white shirt or a high-quality linen top, strikes the perfect balance between style and comfort. The key is to avoid anything that looks too casual: no distressed jeans, loud graphic tees, or athletic sneakers. Leather loafers or refined sandals can elevate the entire look, while a light jacket in a soft pastel shade adds that final touch of polish. Smart casual never means careless — it’s about maintaining a sense of style, even in simplicity.

Where to Shop for Elegant Vineyard Looks in Florence

For those looking to embrace the winery experience with a look that matches the setting, the Jennifer Tattanelli boutique in Piazza Pitti, Florence, is an essential stop. A true icon of Italian elegance and Florentine craftsmanship, her collection blends flowing silhouettes, natural fabrics, and tailored details — perfect for a stylish day among the vineyards.

Standout pieces for wine tastings include lightweight silk or linen dresses, impeccably cut jumpsuits, and leather sandals and bags. Each item reflects a timeless style designed for those who appreciate understated distinction. For visitors in Florence, the boutique offers the perfect opportunity to take home an authentic expression of Italian taste — one you can wear amidst the relaxed yet refined charm of the Tuscan countryside.