Traveling Light: Packing List for Pinehurst and Southern Pines, North Carolina

Opening up my suitcase and sharing my real-life packing list for a chilly weekend in Pinehurst and Southern Pines, North Carolina

What is the closest you’ve cut it while packing for a trip?

For a recent trip to the Sandhills, I think I set a new personal record: only an hour before I needed to be behind the wheel did I have time to haul my suitcase out of the closet and start packing.

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Thankfully, I have not only years of experience packing for weekend getaways, but a host of past packing lists to refer back to when needed here on Wayward. A quick glance at the weather predictions helped me narrow down a previous destination with a similar forecast: Cleveland.

Style-wise, I might not normally equate these two destinations when considering what to pack, but the connection in this particular case was the weather and the timing. There I was, packing for wet winter weather when my heart felt ready to dress for sunny spring days. The solution? Clothing and accessories that would keep me warm and dry, but in lighter colors plus my Springiest (is that a word?) outerwear.

With that, I pulled out my suitcase with an easy-to-pack, built-in organizer, and got packing.

As I usually do once I return home, today I’m sharing my real-life packing list for the Sandhills, my mix-and-match outfit combinations, and some thoughts on what to wear at this unique destination:

PACKING LIST FOR PINEHURST + SOUTHERN PINES

A collage of everything the author packed for Pinehurst — Cashmere Sweater | Long-Sleeve Tee | Trench Coat | White Denim* | Blue Denim | Barrel Pants | Wool Coat* | Sunglasses | Belt | Convertible Bag | Cashmere Cap | Sneakers | Loafers*

PINEHURST + SOUTHERN PINES OUTFITS

Alyssa wears a black top with black pants and shoes — Long-Sleeve Tee | Barrel Pants | Trench Coat | Belt | Loafers* | Convertible Bag | Pearl Necklace | Signet Ring

Friday

In my efforts to hustle out the door and hit the road on a cool, rainy Friday, I reached for a trusty all-black outfit formula to shift my focus to packing the rest of my bag. A sunshiny gingham trench lightened the look, and waterproof loafers* kept my feet warm and dry when the sky opened up.

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Alyssa wears a black top with blue jeans and loafers — Long-Sleeve Tee | Blue Denim | Trench Coat | Loafers* | Convertible Bag | Hoop Earrings | Opal Earrings | Chain Necklace* | Bracelet

Saturday

It drizzled Saturday morning as we explored the farmers market, but eventually, the storm blew through for a fun day of bopping about restaurants and shops. Even though the rain moved on, the grey clouds remained; I was grateful to have my coat with me as we ended the night outside at Red’s Corner.

Is this an accidental approximation of Gen Z’s going-out look? Maybe – but we were here first…

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Alyssa wears a white sweater with white jeans and a camel coat and a baseball cap — Cashmere Sweater | White Denim* | Wool Coat* | Belt | Cashmere Cap | Sneakers

An outfit collage for the author's final day in Pinehurst — Cashmere Cap | Wool Coat* | Cashmere Sweater | White Denim* | Sunglasses | Belt | Convertible Bag | Sneakers

Sunday

Brr… It was so cold on our final morning. The weekend’s earlier storm left behind an icy chill and fierce winds, and for a brief moment while walking to grab a morning coffee, I feared I wouldn’t be warm enough for the day. My worries were squashed an hour or so later as the sun had a chance to work its magic, and I was so grateful to finally see some blue skies.

While packing, I debated bringing along a heavier coat to wear on Sunday, and I’m so glad I tossed it in because I felt comfortable for the rest of the day (same goes for my cap!). Yes, the all-white outfit felt a little bit risky in conjunction with our plans for the day (mini-golf, brewpub), but everything made it out unscathed.

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

ZIPPING IT ALL UP: MY THOUGHTS ON PACKING FOR THE SANDHILLS

Though this packing list was not really what my heart wanted to assemble for a weekend in the pines, I felt perfectly comfortable despite the blustery early spring weather.

But what if you’re visiting the Sandhills during a more typical spring weekend? Spring generally sees warm, pleasant daytime temperatures with cool evenings and a low chance of rain; if my visit fell on an average spring weekend, I would have reached for cool cotton poplin and soft wool cardigans, chic flats, and perhaps a ruffled dress.

As for what locals are wearing, the style in Southern Pines didn’t feel all that different from what people wear most days in Charlotte. As you might expect, over in Pinehurst the style skewed a little more sporty and overtly expensive, with athleisure looks (leggings, chunky sneakers, and an oversized designer bag) and a few collared shirts for good measure. That isn’t necessarily my personal style, but that’s the beauty of fashion: we can opt in or out of trends whenever we please. Note: if you’re staying at Pinehurst Resort, denim and open-toed shoes are not permitted on the golf course, and collared shirts are required at the Carolina Dining Room (learn more here).

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Questions for you

What is your go-to outfit on an unseasonably cold day?

Have you ever pushed the limits when packing? What’s the closest you’ve come to squeezing everything in just in time?

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2 Comments on “Traveling Light: Packing List for Pinehurst and Southern Pines, North Carolina”

Rachel says:

April 16, 2024 at 7:10 pm

What an epic guide to packing light but without missing the fun and flair!

FlywayBetter says:

April 22, 2024 at 9:52 am

Hi Alyssa,
I liked your dressing sense. You wear very good designs which are both comfortable and different in appearance.