Six Go-to Looks for a Long Weekend in Charlottesville, VA

Thanks to stunning vineyards and other wedding venue-ready settings, a venerable university, and an impressive variety of dining and entertainment options, Charlottesville has become a popular fall destination. To help those who may be traveling to the central Virginia city pack the perfect looks and spend a long weekend like a stylish local, we asked Audrey Lewis, owner of the beloved Charlottesville boutique eloise, for recommendations on what to wear and do during an autumn visit to TSG HQ’s hometown. 

Thursday evening

Where to go: Lewis recommends arriving in town in time for drinks and dinner at Tavola (826 Hinton Avenue). Located in the Belmont neighborhood, the restaurant, which serves delicious rustic Italian fare, doesn’t take reservations, but patrons can now enjoy a drink in the recently opened craft cocktail lounge in the back while waiting for a table. What to wear: (clockwise from top left): Clyde patchwork print dress with exposed back zipper accessorized with o-ring knotted leather necklace, pyrite bracelet with pave diamond bead, and open-toe ankle booties.

Friday Daytime

Where to go: Lewis advises antiquing like a local at And George (3465 Ivy Road), The Curious Orange Store (2845 Ivy Road), August 93 (407D Monticello Road), and Stedman House (201 E High Street). Break for lunch at Mediterranean restaurant Orzo (416 W. Main Street [editor’s note: eloise is located just one block away at 505 W. Main Street—be sure to stop in and say hello to your tour guide!]), then enjoy an afternoon facial at Signature Medical Spa so you’ll feel refreshed for your night out. What to wear: Augustina button-up lace shirt, black ankle-length skinny jeans with leather-like coating, striped flannel top.

Friday night

Where to go: Lewis recommends pre-dinner drinks and oysters at Public Fish & Oyster (513 West Main Street) before heading next door to Oakhart Social (511 West Main Street) for delicious small plates. What to wear: Pair your favorite skinny jeans with a bias cami in a champagne-hued silk-like cotton fabric and wool vest with button detail at shoulder and side. Accessorize with an African brass bead necklace by The Woods Fine Jewelry and a 14 carat gold open ring with bicolor tourmaline by Ana Cavalheiro Fine Jewelry.

Saturday sightseeing

Where to go: Enjoy brunch and the beautiful view at the picturesque Pippin Hill Farm & Vineyards (5022 Plank Road, North Garden, VA), then treat yourself to a tour of the University of Virginia grounds. What to wear: Silk crepe flare sleeve dress accessorized with a Feather pendant bracelet and leather bag.

Saturday night

Where to go: Lewis recommends heading to the downtown mall for the evening, beginning with drinks at the stylish bar at the sleek Japanese restaurant TEN (120B E. Main Street) followed by dinner at Fleurie (108 3rd Street NE), a charming restaurant located just off the mall that serves delicious modern French cuisine. What to wear: A yellow, red, and white reef-print Bella dress paired with a Silk thread necklace and Romanesque stackable rings.

Sunday OUt On the town

Where to go: Lewis’s advice for those with a somewhat adventurous side is to take a hot air balloon ride (TSG co-founder Christy Ford agrees that this is an excellent way to take in amazing views of the city!), then enjoy a coffee from Greenberry’s (1049 Emmet Street N) before heading out of town. What to wear: A silk charmeuse mock neck shirt, wool and cashmere Tie-dye poncho, and le garcon boyfriend jeans.   

Read more about Audrey Lewis here, and follow TSG Charlottesville for additional local recommendations when visiting the city.

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