Dressing for Charleston: The Outfits Behind My CHS Guide
Charleston has this effortless way of making you want to get dressed up. Between cobblestone streets, waterfront lunches, boutique hotel lobbies, and beach afternoons on Sullivan’s Island, this city calls for pieces that can move from a morning walk to an oyster dinner without missing a beat. Think easy trousers, a great sundress, something you can throw a caftan over, and just enough gold jewelry to feel finished without overthinking it.
If you caught my Charleston “dressing, dining, and more” post, here’s the full rundown of every outfit – what it is, where it’s from, and why I’d wear it again in a heartbeat.
Look 1: The Everyday Charleston Wander
This look was made for wandering – think King Street shopping, coffee runs, and walking the historic district without a second thought about comfort.
- Zelie Eyelet Embroidered Shirt – An eyelet top is basically the uniform of coastal Southern style. It’s breathable, a little romantic, and pairs with almost anything in your closet.
- Pilon Recycled Cotton Trouser – A relaxed trouser that still feels put-together. Recycled cotton means it’s soft, breathable, and a more sustainable choice for everyday wear.
- Valerie Shoulder Bag in Tan – A neutral shoulder bag that works with every outfit in your suitcase. Tan leather is the ultimate travel color – it goes with everything and only gets better with age.
- Aire Whirlpool Sunglasses in Vintage Tort – A classic tortoise frame that adds a little edge without competing with the rest of the look.
Why it works: Everything in this outfit is a repeat player. None of it is trend-driven, which means it’ll still be in your rotation long after this trip.
Look 2: Dinner-Ready in Navy
This one was built for an evening out – oysters, a good glass of wine, and a restaurant patio.
- Wylie Dress in Navy – Navy is the most underrated dinner-dress color. It photographs beautifully, feels a little more elevated than black, and works in nearly any restaurant setting.
- Berry Hoop Earrings in Hammered Gold – Hammered gold hoops add texture and catch the light beautifully at golden hour.
- Berry Cuff in Hammered Gold – The matching cuff pulls the jewelry moment together without needing a full stack of rings and bracelets.
- Linea 1978 Crossbody Bag – A crossbody is the smartest choice for a night out when you want your hands free for oysters and cocktails.
- Nobuck X Slide – A slide that’s polished enough for dinner but comfortable enough for cobblestone streets – which, if you’ve been to Charleston, you know matters.
Why it works: This is proof that a great dinner outfit doesn’t need to be complicated. One dress, a few gold pieces, and shoes you can actually walk in.
Look 3: Beach Day on Sullivan’s Island
For the days that call for sand between your toes and a caftan thrown over your shoulder on the walk back to the car.
- Rosetta V-Neck Tank Bathing Suit w/ Shelf Bra – A tank-style suit with a built-in shelf bra means support without sacrificing style – ideal for a full day at the beach.
- Elina Caftan in Abira White – A white caftan is the easiest cover-up to throw on for lunch after the beach without changing your whole outfit.
- Earth Goddess Hinged Bangle in Teak – A wood bangle adds warmth and texture that feels right at home on a beach day.
- Nipomo Palma Canasta Bag – This woven basket bag is spacious enough for beach essentials and doubles as a market tote for the rest of the trip.
- CUSHIONAIRE Vita Jelly Sandals – A jelly sandal is a beach-day must: waterproof, easy to rinse off, and comfortable enough to wear from the sand straight to lunch.
Why it works: This is a beach look that still feels intentional – nothing about it says “I threw this on.”
Look 4: Elevated & Ivory
A softer, more polished moment – perfect for a nicer lunch or an afternoon that calls for a little more sophistication.
- Stretch Viscose Yarn Ribbed Sweater – A ribbed knit top adds texture and structure while staying soft and stretchy enough for all-day wear.
- Nico Pant in Ivory, Brochu Walker – An ivory trouser is a chic neutral that elevates any top you pair it with – this one is a closet investment piece.
- Ritla Ballet Flats in Light Pink Crinkle Patent, Dolce Vita – Ballet flats are having a major moment, and this crinkle patent finish adds just enough shine to feel special.
- Shiver & Duke Jade Necklace – A jade pendant adds a subtle pop of color and a little bit of personality to an otherwise neutral outfit.
- Atelier Thin Belt with Buckle – A thin belt to cinch the waist and add definition to an otherwise relaxed silhouette.
Why it works: Pairing a colorful top with ivory trousers keeps the outfit grounded – the neutral pants let the sweater be the statement, while the gold jewelry and pale pink flats tie it all together without competing for attention.
Shop It All
Every piece from every look is linked in my ShopMy – from the everyday basics to the beach day essentials. If you loved any of these outfits, that’s the easiest place to find them all in one spot.
Charleston will always be a favorite for me – not just for the food and the hotels, but for how good the city makes getting dressed feel. See you on the next trip 🤍
July 24, 2026
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