How to Pack for a Summer Trip or Weekend Getaway

Date: May 30, 2024

Close your eyes and imagine your perfect summer vacation. Are you spending a long weekend at the cabin or beach house, drinking coffee on the dock, soaking up the sun on the boat, and cozying up by a bonfire at night? Is it a girls trip to wine country or a romantic getaway for two? Maybe you’re jetting off for two weeks of sightseeing in Europe or renting a house at the beach with friends. Whatever your summer travel plans may be, you’ve got to dress (and pack!) for the occasion.

A woman with long brown hair wearing a green sleeveless top, white pants, and brown sandals is walking outside with a rolling suitcase and a tan handbag. She is also carrying a denim jacket and a woven crossbody bag. This casual outfit is perfect for what to wear on the weekend and is an essential part of a summer vacation packing list.

There’s nothing worse than arriving at your chosen destination and realizing that everything you packed is wrong: you didn’t bring a dress for dinner, the weather isn’t cooperating, you feel like you’re wearing the same outfit over and over. You can’t plan for everything, of course, but with our summer vacation packing list ideas, you can streamline the process and arrive at your destination feeling confident, comfortable, and stylish.

What to Pack for a Casual Summer Trip

A collage of various clothing items ideal for what to wear on the weekend and a summer vacation packing list. The items include a white tank top, a denim jacket, a tan sleeveless top, blue and white striped pants, blue drawstring shorts, a striped long-sleeve shirt, white pants, a blue crossbody bag, and a pair of shell earrings. These versatile pieces are great for casual outfits.

If the only thing on your agenda is relaxation time, you can probably skip the fancier clothes in favor of comfortable but pulled-together pieces that can be worn for morning coffee runs, patio lunches, and days by the water.

A few hero pieces will make your relaxing weekend even more chill. (Less time fretting about what to wear = more time to hang out!) Shorts are great for long walks, pickleball games, trips to town, or pulling over your swimsuit for lunch on the deck. A classic denim short will never steer you wrong; wear it with a lightweight sweater or cozy sweatshirt at night, then dress it up with metallic sandals or slides and a blouse. Elastic waist knit shorts don’t have to scream “I’m at the gym!” Pull-on shorts in linen, twill or woven blends look polished but not fussy.

Just like the denim short, a denim jacket is the ultimate summer multitasker. It goes with everything and isn’t too heavy, so you can wear it over a tank or tee on cool summer mornings, or toss it on for an al fresco dinner in the evening. A sweatshirt is another hero piece; it’s perfect when you need an extra layer, but it can also add a touch of effortless cool to a printed skirt or dress.

What to Pack for a Long Summer Trip

Taking off for a week or more? You’ll want to focus on versatile pieces that you can style in a variety of ways to keep things fresh, so consider adding great basics to your summer vacation packing list.

A woman with curly hair wearing a blue sleeveless dress stands on a sunny beach. She is holding a white tote bag and wearing gold jewelry. This casual outfit is perfect for what to wear on the weekend and is a great addition to a summer vacation packing list.

A simple black or all-over color dress in your preferred silhouette — bodycon midi, fluttery mini, easy tank — is the kind of workhorse you can depend on for long travels. It’s easy to pack and can truly go anywhere, from a casual day of sightseeing in sneakers to a fabulous dinner out with a chic clutch, heels, and jewelry.

Packable knits like skirts and joggers are easy to roll up in your bag, travel well, and can be hand-washed in the hotel sink in case of spills and stains.

Lean into accessories to zshush up the foundation pieces. Scarves and jewelry can easily change the entire vibe of your look, as can a belt bag or tote. (Think belt bag for sightseeing and a tote for impromptu souvenir shopping.) For dressier occasions, a simple yet elegant knit top or sweater can up the glam factor even the most basic dress or pants, especially with a bright lipstick, jewelry, and heels.

If you really want to reduce your packing stress pre-departure, consider one of Trendsend’s Vacation Outfits boxes; each month, we create a custom capsule specifically for travel, which means tops, bottoms, and accessories that are made to love and layer, whether your travels take you to the beach or a Parisian art gallery.

What to Wear on the Plane

A cozy, comfy two-piece set looks chic and pulled together but still prioritizes comfort, especially for long haul flights. We love Spanx’s Out of Office Trouser, an elevated take on the jogger, or their Air Essentials Wide Leg Pant worn with the matching long-sleeved Crew. Breeze through TSA feeling good, even if it’s 4 A.M.

If you’re all about denim, wear your favorite pair on the plane and save precious space in your suitcase. Layer up in a tank underneath a sweatshirt, light sweater, or utility jacket to keep you cozy in-flight, then ditch the layers once you land and wear them throughout your trip.

If you’re not already using packing cubes, this is your sign to pick up a set ASAP. They’re an absolutely brilliant solution to so many packing woes, especially if you’re packing for yourself and kids, or for a variety of events. Hyper-organized people love them because you can keep everything in a designated spot: one cube for pants, one for knits and so on. Overpackers love them because you can pack so much more in your suitcase without sacrificing space. Plus, you can easily toss laundry items in one bag to make unpacking post-vacation a little bit easier. Bon voyage!