Traveling Light: A Packing List for Winston-Salem, North Carolina

After every trip, I like to crack open my suitcase and share everything I packed for a recent weekend away. Today I'm sharing what I packed for three days in Winston-Salem, North Carolina.

In mid-March, Michael and I spent a lovely weekend in Winston-Salem: a charming city with two names and more historical firsts than one could count.

As the city is only ninety minutes from Charlotte, I briefly considered skipping sharing this packing list. I’m not a daily outfit blogger after all – and with comparable weather, the items I packed are essentially ones I would have worn at home that weekend.

But of course, not all of you are from here – and if it’s your first visit to the Carolinas, you may be wondering just what to wear during your trip.

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March often finds this region in False Spring (or the Spring of Deception, if you will), where a warm sunshiny day is immediately followed by freezing temps and bitter winds.

That’s exactly what was forecast for this trip – plus a fun surprise of flurries!

Looking for more packing list inspiration? Discover what's in my suitcase each season: Spring | Summer | Fall | Winter

Warm layers, weatherproof shoes, and a cool pair of sunglasses are all non-negotiable at this time of the year, so I shopped my wardrobe and picked out a few of my current favorites for this trip. I leaned on some hardworking jackets for support by choosing an unusually high number of them (three!), while keeping numbers for every other category at just one or two. But even with the extra outerwear, everything packed right into my Daily Carry-On with room to spare!

Let’s see what went inside, and then we’ll chat about why I chose those items, take a peek at some outfit photos, and wrap up with some tips on packing for Winston-Salem:

WINSTON-SALEM PACKING LIST

All the outfit-makers (minus the undies)

Cashmere Tee* | Cropped Cashmere Mockneck* | Silk Slip Dress | Trench℅ | Wide-leg Jeans* | Wide-leg Pants* | Suede Jacket | Puffer Jacket | Pajama Top | Pajama Bottoms | Weatherproof Boots℅ | Sneakers℅* | Belt | Sunglasses | Crossbody Bag

WHY I CHOSE THESE ITEMS

Each item that goes in my suitcase is carefully considered - even when we're only road-tripping. There's so much freedom in not being burdened by too many belongings - I encourage you to give it a try!

Tops

Cashmere Tee* | As classic as a plain black tee, but with the added luxury of cashmere.

Cropped Cashmere Mockneck* | Warm, cozy, and perfectly suited for high-rise jeans. Pro-tip: this layers beautifully over dresses as well; simply fold and pin the hem to give the illusion of a sweater + skirt combo.

Dresses

Silk Slip Dress | I’ve been wearing this slip dress at least once a week since it arrived (reviewed here), and I show no signs of stopping.

Bottoms

Wide-leg Jeans* | I found these jeans in a clothes swap, and I still can’t believe my luck. They can either read as elevated with heels, or casual with sneakers (which is the direction I went for this trip!).

Wide-leg Pants* | In a wide-leg mood, I added these black pants to my suitcase – perfect for daytime and dinner alike.

Outerwear

Trench℅ | This generously-sized trench drapes beautifully on its own, but also leaves enough room for laying a puffer underneath for added warmth.

Suede Jacket | In the seasonal shift, I love to mix light and dark colors – even when it’s cold outside. This suede jacket is soft and drapey, and the price can’t be beat.

Puffer Jacket | This packable puffer is ultra-lightweight, and belies the amount of warmth it provides. It’s not my favorite style, I admit, but I love tucking it under other coats for extra coziness.

Pajamas

Pajama Top + Pajama Bottoms | Silk is light and easy to pack – plus it feels so luxurious to slip into after a long day of traveling.

Shoes

Weatherproof Boots℅ | With flurries in the forecast, I knew I needed a pair of boots that could stand up to the weather while being delicate enough to pair with my dinner outfits. This pair fits the bill!

Sneakers℅* | A simple white sneaker is such a staple for travel, particularly one with minimal branding.

Accessories

Belt | There’s not much to say about this belt, other than it’s basically perfect.

Sunglasses | Lightweight and with a lifetime warranty, this brand has been my go-to for several years now.

Crossbody Bag* | Bridging from winter to spring in looks, this purse holds way more than its small size implies.

Not Pictured

Undergarments | As ever, I packed this many underwear, some simple camis to wear under my sweaters, compression socks to fight swelling from travel, and my favorite sustainable tights.

Makeup + Toiletries | Most of my toiletries (including my medication organizer, nail set, hairbrush, a few extra hair ties, and my travel curling iron) went right into my handy catch-all case. From there, it was easy just to grab my everyday makeup bag and my liquids bag.

Travel Curling Iron | This teeny-tiny curling iron fits easily into my toiletry bag and somehow doesn’t add too much time to my styling routine. It takes some getting used to curling hair with a shorter barrel, but overall I’m pretty impressed with this little thing.

Jewelry | I decided to keep things extra simple (and all-gold!) by wearing the same pieces for the whole weekend: a pendant necklace (reviewed here), a herringbone chain necklace*, several rings, and a pair of simple solid gold studs that I could wear in the shower.

WINSTON-SALEM OUTFITS

A mix-and-match palette made getting dressed oh-so-easy - a must when the travel itinerary is as packed as this one was!

Alyssa wears a turtleneck and black pants — Cropped Cashmere Mockneck* | Wide-leg Pants* | Trench℅ | Puffer Jacket | Weatherproof Boots℅ | Belt | Crossbody Bag*

Alyssa rides a Segway — Wide-leg Jeans* | Trench℅ | Puffer Jacket | Sneakers℅*

Alyssa wears outfits for dinner — *left:* Cropped Cashmere Mockneck* | Silk Slip Dress | Trench℅ | Puffer Jacket | Weatherproof Boots℅ | Sunglasses | Crossbody Bag* || *right:* Cashmere Tee* | Wide-leg Pants* | Suede Jacket | Weatherproof Boots℅ | Belt | Crossbody Bag*

Alyssa wears a black cashmere tee and jeans — Cashmere Tee* | Wide-leg Jeans* | Trench℅ | Puffer Jacket | Sneakers℅* | Belt | Sunglasses | Crossbody Bag*

Alyssa eats cookies in bed — Pajama Top | Pajama Bottoms

*this item is no longer available and a similar product is linked

FINAL THOUGHTS ON PACKING FOR WINSTON-SALEM

Another successful pack! Despite the wonky weather forecast, I felt like the items I packed served me well for all of our planned activities. Packing for Winston-Salem in the late winter felt a little like cheating because I could just choose a few items and outfits that have been in heavy rotation here at home in Charlotte. But if you’re not from here, of course, you may not have the same luxury and are probably reading this post to try to pin down local style. So – here’s my ultra-short summary:

Style in this region leans a little casual, and a little more classic than super on-trend. Jeans and a tee or sweater are perfect for the daytime most of the year (sundresses are the best way to stylishly combat the summer heat!). But this being the South, people still tend to dress for dinner. Not always in high-glam (though you may see some of this in fine dining establishments), but people here tend to change out of their day clothes and into something just a little more elevated for dinner. Think: an easy dress, tailored jeans, trousers, or a jumpsuit. No need to overthink it; at the end of the day, you should pack a suitcase that feels comfortable for you.

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Are the seasons as unpredictable as this where you live?