In the lexicon of classic destinations, Tuscany continues to draw us in with its unique version of la dolce vita. From the cuisine to the romantic architecture, and from the capital of Florence to the smallest countryside town, it seems like every inch of Tuscany is brimming with picture-perfect scenes to wander through. And fall is the perfect time to do just that, with slightly cooler temps, no throngs of tourists, and lower rates (nearly) across the board. Whether you’re gallery hopping in Florence, wine tasting in Siena, or strolling through the small streets of Castellina in Chianti, we’ve got the right fashion picks to make it look like you holiday there all the time.
Women
Countryside by Day
Tuscany is well known for the gorgeous light that inspired iconic artists like Michaelangelo and Botticelli. Pick up on the spirit by adding a few artsy finishes and rich color to your wardrobe, like these regular rise skinny jeans in a lovely blue ($78). To traverse rolling vineyards or country grounds, stick with flat riding boots. This style by Zara ($199) has interesting antique finishing at the seams. On top, layering is smart for brisk fall days. Start with this cadmium red tank ($9) to wear under a striped sweater with a dash of cadmium yellow ($130). Then, bring along a pair of sunglasses like these tortoiseshell shades by D&G ($134.95).
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Piazza by Night
Bring out your inner artist with a romantic frock done up in a painterly print. This rose print dress in silk twill ($395) has a functional silhouette that can also be dressed down for day. For navigating tricky cobblestone piazzas, stick with sturdy oxford platforms that give just a bit of lift ($110). And in accessories, go with soft lines or a more bohemian natural style like this black suede fringe bag ($98) and bold cuff with cream milk quartz ($60.99). Bring the look together by adding a bit of contrast to the dreamy look. This black leather jacket with oversize collar will inject some cool into just about any outfit in your suitcase ($199.99).
Men
Vineyard Tours by Day
Men’s moutainwear has been all the rage this season, which makes dressing for the country a cinch. Keep in mind, though, that Italy is the land of well-tailored menswear, so mountain-y gear shouldn’t mean ill-fitting. Try this quilted cotton vest in a sun-warmed Tuscan orange (like the color of turning grape leaves), which has a trimmer silhouette than most puffers ($200). Wear the gilet over a flannel sport shirt ($145), like this dyed version by Woolrich in ultramarine blue that’s jazzed up with mother of pearl buttons. For jeans, try an interesting dove gray in a clean straight fit ($79.95 by Hickey Freeman). Finish with casual-meets-dressy Vans, like this handsome colorblock pair in gray and brown ($85), and a sky blue knit cap ($18 by Coal).
Wine Tasting by Night
Dark jeans are a travel staple, like these black dyed classics, and they’re a perfect fit in Tuscany ($235 by Sandro). They’ll take you from a casual dinner under the stars in Volterra to a fancier meal in Florence. On top, go with menswear classics boosted by fun patterns and textures. This button-down by J.Crew ($69.50) features a faint mineral gray stripe, a nice subtle touch that stands out from the rest of the white shirt pack. The centerpiece, however, is this Harris tweed wool blazer, with a feel and color palette that is just right for fall ($350). For extra warmth, layer a burgundy cardigan underneath ($34.95), while stepping into a pair of blue suede booties ($295). Finally, stash your Euros in this bifold wallet with a rustic, rugged charm ($121).
Where to Go This Fall
Booking it to Tuscany in the fall means you’re just in time for harvest season—think wine tasting and olive picking. Choose almost any small town and you’ll find handfuls of bed and breakfast owners and locals happy to help arrange tours, cooking classes, and hands-on workshops. In Cortona (yes, you know it from Under the Tuscan Sun), Casa Bellavista will have you tasting olive oils, learning to cook authentic Tuscan dishes, and touring the countryside by Vespa.
If you’re looking to splurge, book at Mangia Cane, a villa just outside of Florence in Chianti Classico region. The stunning property is surrounded on all sides by green, rolling vineyards. They make three wines on-site, as well as their own olive oil, and are happy to get guests in on the action with cooking classes and tastings. If it’s less hands-on and more luxury you’re after, their spa is intimate and relaxing.
Photo credits: Women: Day: Top left, Sunglass Hut; Bottom left, NET-A-PORTER.COM; Center, Blank NYC; Top right, Target Brands, Inc.; Bottom right, ZARA. Night: Top left, Kirna Zabete; Bottom left, Zappos.com; Center, NET-A-PORTER.COM; Top right, Nordstrom, Inc.; Bottom right, Pacific Sunwear of California Inc..Men: Day: Top left, Nordstrom, Inc.; Bottom left, MRPORTER; Center, GILT GROUPE, INC.; Top right, Sierra Trading Post, Inc.; Bottom right: VANS, Inc.. Night: Top left, Gap Inc.; Bottom left, J.Crew; Center, Arcadia Group Brands Limited; Top right, Opening Ceremony; Middle right: SMCP; Bottom right, MMXII.