What To Wear In Charleston Fall 2021 13 Outfit Ideas For A Charleston Fall | Links + Photo Spots
I’ve got the travel bug… I made my way to NYC in September and LA in October. This month I jetted off to Charleston, South Carolina for a long weekend with my girlfriends! We had the best time eating food, exploring the city, and shooting some content.
Charleston is without a doubt one of my favorite destinations—so much so that it’s at the top of my list for post-grad moves. I wanted to see it during the fall time to get a better feel for it. It’s safe to say I definitely did and of course I was wearing a good outfit while doing so.
As per usual, today I’m recapping all of the outfits I wore throughout my trip with direct links to shop. Plus, I’ve linked the photo locations so you can recreate these pics! For reference, Charleston is about seventy-high sixties this time of year with brisk mornings and evenings. I recommend light layers but if you’re coming from the Midwest the constant sunshine is going to be a treat either way!
(click pink text for links to clothing items and/or photo locations)
Cuter Than Your Grandma’s Sweater
Nothing screams Charleston quite like a flowy maxi dress and a good felt hat. When scouring Pinterest for Charleston outfit ideas, my feed was flooded with similar outfits so I figured this gingham dress from Petal and Pup was perfect. It’s rather shapeless which means you can enjoy all of the yummy food this city has to offer without fear of your pants being too tight!
It runs a little long so I recommend a small heel for a little lift. These shoes are from Chinese Laundry and were super manageable for a day full of walking.
sweater // pants // shoes // hat
photo location ✈ Palmetto Montessori
Saturday Stroll On King Street
Nothing screams Charleston quite like a flow maxi dress and a good felt hat. When scouring Pinterest for Charleston outfit ideas, my feed was folded with similar outfits so I figured this gingham dress form Petal and Pup was perfect. It’s rather shapeless which means you can enjoy all of the yummy food this city has to offer without fear of your pants being too tight!
It runs a little long so I recommend a small heel for a little left. These shoes are from Chinese Laundry and were super manageable for a day full of walking.
photo location ✈ Palmetto Montessori
Orange You Glad
I was sent this sweater for a sponsored Tik Tok and truthfully wasn’t sure when I’d get to wear it again. I had been saving these orange linen pants specifically for this trip and decided this patterned sweater would be perfect on top. I gave it a quick bra tuck to make it cropped and called it a day!
For shoes, I slipped into white heels. I know it seems a little weird to wear heels with this outfit (it def is) but these pants just need a heel with them. I tried on everything: boots, mules, sneakers, and nothing looked as good as this. Trust me. This would be the perfect look for dinner and will keep you warm while outdoor dining.
photo location ✈ the building next to Palmetto Montessori
Cutie In Crochet
Strolling through Folley Beach in the cutest crochet tank top. I grabbed this from Princess Polly and know I’ll get tons of use out of this come summertime. It’s got a halter neckline and laces up the back. Layer on some gold jewels + pop on a pair of lightweight pants and you’re good to go for a trip to this beach town. I recommend throwing a cardigan over the top as it gets a little brisk by the water in the mornings/evenings.
photo location ✈ W Arctic Ave
Feeling Like Fall
It definitely was a little chilly in the mornings with people everywhere exploring historic buildings and getting tours of the beautiful side streets. Devon and I stumbled across this adorable brown truck and I knew I needed to snap a photo in front of it. If you’re headed to any of Charleston’s rooftops for a few drinks, this outfit would be perfect!
This sweater is super thick with the most amazing neckline and cap sleeves. I tucked it into brown leather pants that are so on-trend and popped on a pair of heels for a little bit of lift. Don’t forget a chain-link crossbody to match. This city screams old money so I’ll carry my $13 SheIn purse and try to fit in, lol.
sweater // pants // heels // purse
photo location ✈ 26 Meeting Street
Side Street Smiles
I took photos in front of this historic house the first time I visited Charleston and just had to stop by again this trip. Lightweight long sleeves are perfect for the daytime here. Plus, you can’t go wrong with a pop of color. I slipped into (okay, more like squeezed into) the cutest white jeans from Princess Polly. These run so small so I highly recommend going up a size to make them fit. Heels for the photo were perfect but sneakers are definitely the better bet for walking around the cobblestones streets.
photo location ✈ 60 Meeting Street
Mama Mia Moment
I got this adorable blue two-piece set from Princess Polly and knew I had to bring it on this trip. Where else am I going to be where I can wear a halter top in the middle of November?! These pants are so flattering making your waist look extra tiny and your booty extra perky. Throw on heels and a cute bag for your modern-day Mama Mia moment.
photo location ✈ 35 Tradd Street
Little Black Dress Day
There’s just something about a maxi dress that works so well in Charleston. They keep your legs covered so I was the perfect temperature while wearing this. This wrap-front dress was another Petal and Pup dress. It’s adorable but runs a little tight in the bust so I would recommend sizing up.
These dresses speak for themselves. Pop on a sandal, mule, or low-top sneaker: whichever works for you. I went for sandals trying to soak up every ounce of sunshine. My black bag is new from Polene and it was the perfect size for this weekend trip. It fits my wallet, camera, and phone and can be worn as a crossbody or on the crook of your arm!
photo location ✈ Taco Boy Downtown
Casual in Charleston
I packed this as a “just in case” outfit and ended up changing into it on Sunday afternoon for some exploring + dinner. As warm as it can be during the day, it cools down in the evening so a chunky cardigan was a must. This one is from Princess Polly and has the perfect oversized fit. Underneath, I’ve got on a basic Body Contour tank from Express.
These jeans are some of my favs from Lulus and my Dolce Vita sneakers are the best for walking around cities. I bring them on every trip and they never disappoint. I know this outfit isn’t anything super special but tons of locals and tourists were wearing variations of this so I wanted to be sure to include it.
Let’s be real… nobody else was wearing a blue Mama Mia set haha.
tank // cardigan // jeans // sneakers
photo location ✈ The Four Winds Inn
Elle Woods, Is That You?!
Let’s be real, I definitely needed this neon pink three-piece blazer set from Fashion Nova. Like needed. I’m wearing an XS in this and it fits me perfectly. The top looks like a little bra, self-tying along the back. However, as tiny as it is these trousers are so high-waisted that there’s hardly any of your stomach exposed.
Of courses, this did come with a matching blazer and my gosh is it perfect altogether. I felt like such a girl boss in this and want to frame these photos as it’s been forever since I felt this confident.
photo location ✈ US Postal Office
Loving On Leopard
I’ve had this dress sitting in my closet for a few months now and decided Charleston would be the perfect time to pull it out. The brown and creme leopard is perfect for the fall and the long bishop sleeves are to die for. This dress was more of a midi then a maxi, so I figured a small dainty heel would be perfect with it. I felt so darling in this! Truly the perfect dress for brunch, or a Sunday stroll.
photo location ✈ 60 Tradd Street
Sweets In Sullivan
Sweet treats in Sullivan’s Island call for a basic outfit. I’m keeping things causal with my got to duo: a flannel and a long sleeve sweater. Both of these pieces are Princess Polly and the color combo was bomb for this time of year. Plus, light layers are needed when you’re by the water.
I get so many questions about these straight-leg jeans: they are some of the only ones I’ll wear as they actually fit my waist and are just the right length. They work best with platform sneakers.
flannel // long sleeve // jeans // sneakers
photo location ✈ The Bearded Cat
Wheels Up
As much as I do love a trendy airport fit, some flights just call for a cozy set. I get almost all of my loungewear from Whitefox Boutique and they truly never let me down. This set is a terry cloth material so a little lighter in weight then some of their other fleece sets. Wearing this with sneakers to keep things simple.
sweatshirt // joggers // sneakers // suitcase // backpack
photo location ✈ Charleston Airport
pin this post for later!
Agh, I can’t believe I was able to pack thirteen outfits into a three-day trip! I wouldn’t put it past me though—I wanted to give you a wide variety of statement pieces and items for everyday wear. There’s so much to do and see in Charleston that there is truly an occasion for every outfit.
I had the best fall visit and cannot wait to be back soon. Here’s to good outfits and an even better time. Stay tuned for my full travel guide coming later this week.
With love, McKenz
Latest Post: Weekly Wrap Up #47 2021
Related Post: What To Wear In Charleston Summer 2021
Instagram: styledbymckenz // YouTube: McKenzie Morgan // Pinterest: mckenzmorgan
