Radcliffeborough

Set up like a cool, rustic bachelor pad rather than a standard men’s store, Brett Carron’s five-year-old shop is devoted almost exclusively to U.S.-made clothing and accessories. As the name suggests, a lot of attention is paid to jeans, the majority of which are made of selvedge denim in limited runs. The rest of the buy is equally thoughtful: shirting from Gitman Brothers Vintage, watches from Shinola, and Billykirk leather accessories.

One of the most recommended restaurants in Charleston, Halls Chophouse is the place to go in the city for steak. It's also a favorite Sunday brunch spot. Which means you should make a reservation early as Halls books up quickly. After eating here, walk a block down to The Cocktail Club for a handcrafted drink.

Cannon Green’s gorgeous interiors justify a stop regardless of their food (which, incidentally, is excellent); they’re so stunning that the space actually doubles as a wedding venue. The high-ceilinged central room opens up to a huge back patio lined with twinkle lights and palm trees—from the inside, you can take a curved staircase along the bar to a mezzanine and access to a side porch that looks out over the aforementioned patio. Their cocktails are excellent, so we love it for Sunday brunch, when they set up a DJ booth outside, or for happy hour on cool summer evenings.