My Favorite Looks from Our Weekend in Charleston

Here’s the thing: I had every intention of planning my outfits for Charleston. I even made a moodboard—neutrals, linen, a pop of rust. But by the time I actually packed, it turned into a mix of what I felt like wearing and what wasn’t wrinkled beyond repair.

And honestly? That worked better.

Charleston feels dreamy in a way that makes you want to dress up a little—but not too much. It’s slow coffee mornings, golden hour on the water, and dinners where you dress for the vibe, not the dress code. So instead of forcing looks, I reached for pieces that felt easy, familiar, and just elevated enough.

This post isn’t a packing list or a “how to dress in Charleston” guide. It’s just a snapshot of what I wore, what I loved, and how each outfit made me feel—because that’s what I always end up remembering anyway.

Why Charleston and Why These Outfits

Charleston has this quiet confidence about it—pastel facades, oak-lined streets, and just the right amount of Southern charm. It’s the kind of place that makes you want to slow down and dress with intention. Not for show, but for feeling like yourself (with maybe a little extra polish).

Setting the Scene

We booked the weekend on a whim—two nights, no strict plans, just a shared notes app of cute restaurants and vintage spots to check out. The weather looked promising: low 80s, humid but manageable. So I packed light, leaning into easy layers, breathable textures, and a color palette that worked from coffee run to cocktail hour without needing a full outfit change.

A few staples came with me: the blazer I always end up rewearing, two dresses that could pass for day or night, and sandals I trust on cobblestones. I didn’t aim for perfection—just comfort with a side of “let’s pretend I planned this look.”

Style Mindset for the Weekend

I went in with three goals:

• Nothing fussy — no outfits I’d have to adjust every five minutes.
  
• Everything remixable — so I could swap pieces without starting from scratch.
  
• Me, but slightly more vacation-ready — like adding a scarf to a ponytail just because I had the time.

Friday’s Travel and Dinner Look

First outfits on any trip always feel a little high-stakes. You want to be comfortable but still feel like you’re arriving somewhere—not just surviving TSA and recycled plane air. Luckily, this one hit that balance.

The Travel Outfit That Held Up

I’ve learned not to overcomplicate travel looks. This one was simple: a ribbed black tank, soft tailored trousers with a forgiving waistband, and my go-to lightweight trench that somehow always makes me look put-together—even when I’m on hour three of bad airport coffee.

The real MVP? A crossbody that fit everything but didn’t scream “tourist.” It slid under the seat in front of me without a fuss and still looked good enough to carry to dinner.

Also: sneakers. Always sneakers. No matter how chic ballet flats look on Instagram, they never survive airport security lines or “just a few blocks” that turn into a 30-minute walk.

Quick Change for a Rooftop Dinner

We landed, checked in, and had just enough time to freshen up before heading to a rooftop spot with string lights and way-too-good fries. I didn’t do a full outfit change—just a little remix.

• Swapped the sneakers for block-heeled slides
  
• Added gold hoops and a deep berry lip (the kind that makes you look awake, even if you’re not)
  
• Pulled my hair into a low twist with a claw clip I nearly forgot I packed
  

The look still felt like me—just a slightly shinier version. And most importantly, I wasn’t thinking about it all night. I was present, comfy, and honestly just happy to be somewhere with good drinks and no inbox notifications.

Saturday in the City: Exploring + Sunset Drinks

This was our “do everything and nothing” day. We had a loose itinerary—brunch, vintage browsing, art galleries, maybe a spontaneous spritz stop. Basically, I needed a look that could last all day and still feel fresh by sunset. Spoiler: I got halfway there.

Morning Market Look

I started the day in what I call my “soft uniform”: an oversized button-up (borrowed from his side of the closet), crisp shorts that don’t bunch when I sit, and Dr. Scholl’s Original Collection Sandy Sandals — the kind of shoe that handles cobblestones, humidity, and last-minute detours without ever complaining.

I grabbed a canvas tote, added a pair of square-frame sunglasses I didn’t baby all day, and tied a silk scarf into my hair to pretend I had a plan.

We wandered the farmers’ market, stumbled into a bookshop with mint iced tea, and found a shady bench that turned into an impromptu photo spot. The look felt breezy but still like an outfit. Big win.

What I Changed Into for Golden Hour

Around 5pm, I did a quick room refresh — because Charleston golden hour deserves an outfit upgrade. I swapped into the Farm Rio Open-Back Scalloped Broderie Anglaise Linen-Blend Midi Dress, which felt like the breeze had a dress code. Open back, scalloped details, and just structured enough to feel intentional without feeling overdressed.

I added a gold cuff I always forget I own, kept my same crossbody from Day One, and yes — the same sandals again, because they absolutely earned their keep.

I skipped foundation and went with a little skin tint and cream blush—because sticky evenings call for less. The dress moved beautifully in the breeze, and I didn’t once wish I packed something else. That’s a rare feeling, and I noted it.

Sunday Brunch + Farewell Walk

There’s something about the last day of a trip that makes you want to stretch it out—slow coffee, long walks, and an outfit that feels like you tried, but not too hard. That was the energy going into Sunday.

Brunch Outfit MVP

I pulled out the Banana Republic Ariella Poplin Midi Skirt — almost didn’t pack it, and so glad I did. Just the right amount of volume and crispness, roomy enough for mimosas, and it made me feel styled without being styled at.

🍊 This skirt carried me through brunch, a second mimosa, and a farewell walk.

Find it here if your wardrobe’s missing that easy, elevated go-to.

I paired it with a simple tucked-in tank and layered the same travel blazer over my shoulders like I had my life together. 🧡 If you’re after the perfect poplin skirt, this one’s a total winner and will elevate your everyday looks! ✨

It felt like the kind of look that works for brunch or pretending you didn’t pack your suitcase at midnight the night before. I added subtle gold hoops, brushed out my hair, and kept my makeup minimal but glowy. Honestly, I’d rewear the whole outfit for a city day back home—with sneakers and a big tote.

Walk Look (Same But Slightly Less Styled)

Post-brunch, we wandered back toward the waterfront. The blazer got folded into the tote (sorry, blazer), and I pulled on a cropped hoodie I’d packed for “just in case” moments. It ended up being the perfect layer once the breeze kicked in.

I ditched the earrings, kept the same skirt and tank, and swapped in a bit more SPF and chapstick. Still felt like me, just a more practical version. And it’s always a good sign when you’re already thinking of ways to rewear the same pieces next weekend.

What I Loved and What I’d Tweak

Every trip teaches you something about your closet—what you actually reach for, what holds up, and what ends up sitting in the bottom of your suitcase, untouched. Charleston reminded me that good outfits don’t need to be overthought. They just need to work with you, not against you.

These are the items I’ll keep in rotation, not just for trips, but for ‘don’t-know-what-to-wear’ days at home. 💼 Whether you’re traveling or styling your everyday looks, this sandal will quickly become your go-to. 👗

Repeat-Worthy Pieces

The blazer I wore three different ways? A hero. It instantly pulled every look together without making anything feel stiff. My sandals handled every cobblestone, staircase, and detour with zero complaints. And that linen dress from Saturday night—easily the most complimented piece of the trip, and I never once felt overdressed.

These are the items I’ll keep in rotation, not just for trips, but for “don’t-know-what-to-wear” days at home.

What Didn’t Make the Cut

A pair of wide-leg pants I brought thinking they’d feel elevated ended up stretching out in a weird way by day two. And a slinky halter dress that looked great in theory didn’t match the mood of anything we actually did. Pretty? Yes. Practical? Not even close.

Lesson learned: if it only works for one specific moment, it probably won’t earn its space in my carry-on.

Would I Pack These Again?

Honestly, yes. Not because every piece was perfect—but because most of them felt like me. And that’s what I’ve been chasing more than trends or TikTok hauls lately: a closet that’s built around clothes I actually want to wear, again and again.

Style is personal, but good taste speaks loud.