September is the month Charleston finally exhales. The tourists thin out, the humidity breaks (eventually), and the calendar fills up fast with ArtWalk on September 4, the Lowcountry Jazz Festival September 4 through 6, live shows at the Charleston Music Hall all month, and the MOJA Arts Festival running September 24 through October 4. Add in the last stretch of the Charleston Farmers Market at Marion Square and you have a full month of reasons to leave the house looking put together.

If you have been asking what to do in Charleston in September, the short answer is: almost everything, and almost all of it outside. This is the transition month. It is still warm enough for a sundress at 6pm but cool enough that you will actually want your linen blazer by 9. Here is how I am building my September, event by event, outfit by outfit.

First Friday ArtWalk Sets the Tone (September 4)

Every first Friday, the galleries along Broad Street, King Street, and French Quarter fling their doors open for ArtWalk, and September’s edition kicks off the month exactly the way it should: unhurried, a little dressed up, wine in a plastic cup because that is just how it goes downtown. It is free, it is walkable, and it is the easiest way to fill a Friday night without a reservation.

What to wear: a linen shirt dress you can walk five blocks in, flat sandals, a crossbody bag with room for a business card or two if you fall in love with a local painter.

Lowcountry Jazz Festival Brings the Soundtrack (September 4 to 6)

The same weekend, the Charleston Gaillard Center hosts the Lowcountry Jazz Festival, an annual Labor Day weekend tradition that pulls in serious talent for a few days of live sets in one of the city’s most beautiful venues. If you want a reason to get dressed up before Labor Day slips away, this is it.

The Charleston Music Hall Calendar Stays Busy All Month

Beyond the festivals, the Charleston Music Hall has a genuinely packed September, with acts like Switchfoot, comedy nights, an evening with author Jodi Picoult, and more filling the calendar through the month. If your September plans need a built-in date night, this venue alone can carry you three or four weekends in a row.

What to wear: this venue runs a little more elevated, think a slip dress or a tailored trouser and a good boot, since you are indoors and the lighting is flattering.

MOJA Arts Festival Closes Out the Month in Style (September 24 to October 4)

This is the big one. The MOJA Arts Festival is Charleston’s long-running celebration of Black arts and culture, spanning visual art, music, dance, and spoken word across venues throughout the city, and it is the kind of event that rewards showing up more than once. It technically bridges into early October, which makes it the perfect bridge event for a September that is not quite ready to become fall.

Locals treat MOJA as a full ten days rather than a single afternoon. If you only have room for one big event this month, make it this one.

Don’t Skip the Charleston Farmers Market

The Charleston Farmers Market at Marion Square runs Saturdays through November, and September is arguably its best month. The heavy summer heat has broken slightly, the produce is shifting toward early fall, and it is still the single easiest way to build a Saturday morning around good coffee, good produce, and a walk through downtown.

Pair a morning at the market with a stop at one of our favorite Charleston coffee shops for a proper start to the weekend, then carry your tote straight into an afternoon browsing Lowcountry interior finds if you are the type who cannot walk past a good antique booth.

A Few More Worth Watching

• The Wizard of Oz at the Historic Dock Street Theatre runs through late September, a sweet option for a family afternoon or a nostalgic date.
• Concert and comedy dates continue rolling through the Music Hall calendar most weekends, so it is worth a quick check before you lock in Saturday plans.

Building Your September Around These Events

The through-line for a good Charleston September is simple: mornings at the market, evenings at a gallery or a show, and at least one weekend given fully over to MOJA. Keep your wardrobe light and layered, because this month swings from warm afternoons to genuinely pleasant evenings, often in the same day.