What to Wear in Charleston: Cobblestone Footwear, 'Charleston Smart-Casual' Dining & Marsh Bug Spray

Here is a helpful cultural tip comparing the two Lowcountry sister cities: while Savannah is bohemian and relaxed, Charleston is noticeably more preppy, polished and traditional in how locals and visitors dress, especially at dinner. Packing a mix of breathable daytime walking clothes and one or two smart-casual evening outfits ensures you feel right at home everywhere from Folly Beach to King Street.

Four Practical Packing Rules for Charleston

1. Cushioned Flat Trainers, Loafers or Flat Sandals (Avoid Stiletto Heels on Cobblestones): Charleston's oldest pavements are laid with uneven 18th-century bluestone slate flags, handmade bricks lifted by live-oak roots, and rounded river-ballast cobblestones (on Chalmers Street, Philadelphia Alley and Longitude Lane). Narrow heels catch in the gaps easily, so wear cushioned walking shoes or supportive flat sandals for daytime walks.
2. Respect Charleston's Evening 'Smart-Casual / Jacket Optional' Dining Dress Codes: unlike beach towns where shorts and flip-flops go everywhere, many of Charleston's top restaurants, including Hall's Chophouse, Peninsula Grill, Charleston Grill, Circa 1886, Husk and FIG, enforce an evening dress code: no athletic gym shorts, no sleeveless vests for men, no baseball caps indoors, and no rubber beach flip-flops. Pack a collared button-down linen or cotton shirt or polo with chinos or neat dark jeans for men, and a sundress, midi skirt or jumpsuit with a light cardigan (for indoor air-conditioning) for women.

3. Linen, Cotton & Moisture-Wicking Fabrics for Late Spring & Summer (+ A Small Umbrella): from May through September, high coastal humidity makes synthetic polyester feel clammy; stick to natural linen, seersucker and light cotton, and keep a compact umbrella in your bag for passing afternoon summer showers (when walking during a heavy Charleston rain shower, low-lying intersections at Market Street and Crosstown drain slowly at high tide, so avoid wading through street puddles).
4. Bug Spray for Plantation Swamp Gardens & Marsh Sunsets: when walking the cypress boardwalks at Magnolia Plantation, Cypress Gardens or the Angel Oak, apply Picaridin or Lemon-Eucalyptus repellent against coastal sand gnats (no-see-ums). Check seasonal weather.