The packing strategy for a weekend trip can take many forms. Some people love a well-thought-out packing list while others throw a bunch of stuff in their bag last minute hoping it all works back together. The former method usually works out best, especially for longer trips where multiple activities are planned. But even for a short trip, thinking through your style strategy can save a lot of time and stress.
To help with this article, I asked three of my most stylish friends and frequent travelers for their ultimate weekend packing list with chic ideas for different destinations. Here they break down their favorite outfit, must have shoes & accessories, most-loved weekend bag and can’t-live-without skincare they packed for a recent trip.
Warning: if you are looking for practical tips, this might not be the place! But, if you want ideas for how to look stylish on your next weekend getaway and for specific items these stylish travelers never leave home without, read on!
Lexi James Tawes with friend Karen Chiarucci, Napa Valley, Chanel Shoulder bag
CALISTOGA
Lexi James Tawes
Lexi is a San Francisco based fashion exec who has the most covetable, never-goes-out-of-style, forever-chic, perfect-for-every-occasion wardrobe. She frequently travels north into wine country to spend time with family and friends. Wine country is usually a short getaway, a 3-day trip max even if traveling from the east coast, and Lexi knows how to do it stylishly; packing versatile items that can take you anywhere from Napa to Sonoma to Calistoga.
the SHIRTDRESS:
The ultimate travel item in my bag is this boyfriend shirtdress, which goes from wine tasting to the pool effortlessly.
the PURSE:
This Chanel shoulder bag is the perfect size to carry around all of your essential items and more. (travel documents, credit cards, phone charger, you name it) Plus it’s forever stylish with its gold chain strap and quilted white leather.
the SKINCARE:
If I had to pick one cosmetic item to travel with it’s La Mer’s The Essential Tonic. It cleanses and hydrates and my skin never looks better than right after I use it. Once you try it, you’ll wonder how you ever lived without it!
the SHOES:
These Valentino espadrille mules are my favorite versatile shoes that go with so many different outfits. Plus they are easy to walk around in and see the sites.
the SWEATER:
I’m known to love a classic stripe and this cotton sweater from Kule is the perfect day to evening to plane sweater, no matter what time of year it is. Wear it alone, layer under a light jacket or throw it around your shoulders. (Lots of layers is always a good idea when traveling!)
the SUNGLASSES:
Sunglasses are essential as wine country is all about being outdoors in the vineyards, dining al fresco or sitting out by the pool. Make sure you pack a chic pair like these Celine geometric sunglasses.
the BRACELET:
I like to bring one piece of jewelry that can go back to anything day or night and this Baacal bracelet is the perfect statement piece.
the WEEKEND BAG:
Louis Vuitton’s Keepall Bandolier 50 (aka the chicest duffel bag ever made) is my go-to weekender bag.
Lee Hayman, Martha’s Vineyard, Seashell Earrings
MARTHA’S VINEYARD
Lee Hayman
Lee Hayman is an LA based stylist who is originally from Martha’s Vineyard. She has an enviable, effortless style that you want to imitate no matter which coast you’re on. She let us in on the perfect must-have items to wear when visiting her hometown if you’re planning your own weekend adventure.
The Vineyard has a reputation that isn’t entirely true. Most people think of it as a destination akin to the Hamptons, a playground for only the rich and famous. And while many former presidents spend their free time relaxing there, the Vineyard, to the locals, is about as laid back as it gets. When I visit my parents, I go for comfort and coziness over what I might wear in LA. But I think the below pieces give you the best of both worlds – comfort and fall chicness.
This is what I would pack for that perfect long weekend trip in the fall. Don’t forget to go to Morning Glory Farm and get a homemade pumpkin square for me, please!
the COAT:
When I moved to LA I swore I would never miss the cold, but I do miss the coats. I just want to wear a trench coat and not boil by 12pm. I have been dreaming of brown suede everything this fall, and this Nour Hammour chocolate brown suede trench is perfection.
the SWEATER:
A tried and true Vineyard fall outfit – a pair of jeans and a sweater. Don’t fix it if it ain’t broke. Pair your jeans with this cotton sweater from The Knotty Ones, a female founded and run Lithuanian based company focused on small batch sustainability and supporting their artisans.
the JEANS:
The best barrel jeans I’ve found are Tibi’s Sid Jeans. My favorite part of this silhouette is they look “fashion,” but feel “comfort.”
the SHOES:
These Mango loafers are the perfect burgundy color. Pop them with a cute sock when it’s chillier out for a walk through town.
the CARRY-ON BAG:
I use this MZ Wallace duffle as my carry-on bag. It has lots of pockets for extra space and it’s easy to travel with but fits a lot! Love the brown colorway for fall.
the SUNGLASSES:
You’re on island time, of course you’ll need some sunnies. These ones from Le Spec are my go to, and elevate any outfit.
the SKINCARE:
At home on the Vineyard or back in LA, 99% of my free time is spent at the beach, regardless of season. I wear this Shiseido sunscreen daily, and have gotten all my friends hooked on it. It actually smells good and feels amazing to put on.
the SOCKS:
The flight from the west coast is loooong. My mom got me a pair of compression socks one Christmas – first I made fun of them, now I cannot fly without them. Don’t knock it ‘till you try it!
must VISIT:
The best part of travel is shopping, of course! You can make the cutest custom necklaces to wear on vacation and take home with you from The Charm Bar at my favorite Edgartown shop, SeaLegs. I have one with an evil eye heart, “LOVE,” and palm tree charms.
Susan Moses on vacation, St. Barths, Book by Chris Whitaker, Celine Sunglasses
ST. BARTHS
Susan Moses
Susan is a close friend who clearly understands the art of packing. We travel together once or twice a year and she always (and I mean always) has the perfect outfit for everywhere we go. Whether it’s a night out dancing, a morning hike or lunch at a beach club, Susan always shows up in the perfect thing. Turns out she makes a list of everywhere we are planning to go on our trip (plus she checks the weather forecast!) and packs an outfit for each activity accordingly. I now consult with her ahead of time so that I can do the same! Here is what she is packing for an upcoming weekend getaway to St. Barths:
the DRESS:
St. Barths is both casual and incredibly chic and so is this dress. This black strapless eyelet dress from Matteau can go anywhere on the island, day or night. Wear with flip flops for a drink by the pool or nice sandals for a nice dinner out with friends.
the BAG:
This raffia tote is the perfect bag to carry your essentials in plus any additional items you pick up throughout the day. Plus the design of it allows for easy access to anything you need!
the MAKE-UP:
This Hermes mineral powder adds a healthy sun-kissed glow to your skin, which is exactly what you want on an island retreat! Plus the design of it is so beautiful.
the SANDALS:
I like to pack sandals in neutral colors so they go back to everything in my suitcase. These black strappy sandals are by French brand K. Jacques so they feel like the perfect pair to bring to the French island.
the SUNGLASSES:
Chic sunglasses are key in St. Barths! These neutral Celine frames look great on everyone and pair back to everything, casual or dressed up.
the TOP:
This crochet top with fun pops of color makes me happy. It’ll go back to jean shorts for lunch out or over a swimsuit by the pool.
the SUITCASE:
If you are not someone who likes to pack light (guilty!) or loves to pack an extra pair of shoes (also guilty!), this Away carry-on has a lot of space. Plus this olive color is so cool and never looks dirty.
the SUNSCREEN:
Sunscreen in the islands is a must and Supergoop’s Unseen Sunscreen with SPF 40 is the best. It’s transparent and weightless which is perfect to reapply on your face throughout the day. Plus I love travel-sized toiletries and this comes in the perfect mini size to keep in your bag at all times.
