1. A chambray jumpsuit that checks one outfit off the list and takes up the size of just one garment. Solo, it's a jumpsuit. Throw a shirt on top, now it's a top and pants.

Lane Bryant

Price: $99.95 (available in sizes 12–28)

2. A macrame cutout midi dress here to give you pretty cool tan lines if you wear it to lie in the sun. One moment it's a breezy dress to throw on for lunch on the water, and later, you can wear it as a nightshirt.

Lane Bryant

Price: $39.97 (originally $79.95; available in sizes 10–40 and two colors)

3. A dollman V-neck top you can French tuck into a pair of jeans, twist and tie to turn into a crop top, or wear as a cover-up over your swimsuit.

Lane Bryant

Price: $36.95 (available in sizes 10–28 and five colors)

4. A denim high-rise maxi skirt that'll get you from the beach back to your room after taking a dip in the ocean. And it's denim, so it goes with *everything* in your suitcase.

Lane Bryant

Price: $79.99 (originally $89.95; available in sizes 14–24)

5. A pair of patterned gauze shorts so your legs can finally get some sun. When you return home, no one will mistake you for a member of the Cullen family from Twilight.

Lane Bryant

Price: $49.95 (available in sizes 10–40)

6. A ruched-side tee for a top with a bit of added personality that's ultra thin and therefore folds really small, taking up practically no room in your bag. And it comes in 18 colors and patterns, so grab five, throw them in the bag, add one pair of shorts, a skirt, and a pair of pants, and you're good to go.

Lane Bryant

Price: $29.95+ (available in sizes 10–40 and 18 colors)

7. An off-the-shoulder top, because nobody should travel six plus hours to a resort and not pop out the shoulders. A casual yet sexy top you can mix and match with all your bottoms that'll still keep you as cool as possible.

Lane Bryant

Price: $42.95 (available in sizes 10–28)

8. A beautiful floral pant filled with a variety of colors you can pull from to match, or you can go super low-key and just pair with a basic white cami. Shoes? A pair of slip-on sneakers will suffice. The pants have done all the work for you.

Lane Bryant

Price: $89.95 (available in sizes 12–28, including long fits)

9. An open-stitch cardigan with the same versatility you'd get from the bulky duster you left at home. Only this time, there's an open stitch which gives you a well-ventilated option when the humidity rises.

Lane Bryant

Price: $59.95 (available in sizes 10–28 and three colors)

10. A striped button-down top — when it's not clocking in as your shirt of the day, it can be used as a lightweight shacket. And if things get too warm and you have no place to put it, just tie it around your waist.

Lane Bryant

Price: $59.95 (available in sizes 10–28 and two colors)

11. A pair of high-rise biker shorts you'll probably already be wearing before you even get to your trip because they're super comfy for travel. Plus, if you want to keep up your active routine while on vacation, you'll already have your gear.

Lane Bryant

Price: $44.95 (available in sizes 10–40)

12. A matte black jersey skirt with a side slit that can be dressed up or down depending on the top and shoes you pair with it. The slit will always be partying, or should I say, ~parting,~ because it wants that leg to be seen.

Lane Bryant

Price: $59.95 (available in sizes 10–28, including petite fits)

13. An *out of office* tee, as if you need the reminder. Your bestie who keeps checking their work email while you're waiting to check out the museum should take note of the message on your shirt. "Hey, you, eyes on me."

Lane Bryant

Price: $42.95 (available in sizes 10–40)

14. A denim skort to give you the bessssst of both worlds. 🎶 Hannah Montana would agree that wearing a skirt with shorts already built in, allowing you to move freely without fear of flashing the undercarriage, is pretty top-tier.

Lane Bryant

Price: $69.95 (available in sizes 12–40)

15. A rhinestone rainbow graphic tee hopefully featuring the same rainbow and palm trees you'll see on your trip.

Lane Bryant

Price: $42.95 (available in sizes 10–40)

16. A relaxed denim pull-on pant with the comfort and roominess that you'd get from a pair of sweats, with the structure of a traditional jean. Plus, you're OOO, your vibe is super chill, and there are few things more chill than just slipping on your pants. No buttons or zippers to fuss with.

Lane Bryant

Price: $89.95 (available in sizes 12–40, including petite, short and long fits)

17. A pair of skinny jeans because every now and then we want a little something that hugs our curves oh-so-right. And while we've been wallowing in the comfort of the wide leg fit, we can't resist returning to this style.

Lane Bryant

Price: $79.95 (available in sizes 12–40, including petite, short and long fits)

18. A high-neck ribbed tank because you can never pack enough tops when visiting the blistering heat of Palm Springs. And for this reason, you'll cherish every additional tank you have on board. Especially when you've just sweated through your initial tank of the day.

Lane Bryant

Price: $32.95 (available in sizes 10–40 and 13 colors)

19. A cotton cami great for layering under your button-down top, wearing solo *or* wearing underneath a garment that boasts too deep of a V neckline for your comfort.

Lane Bryant

Price: $22.95 (available in sizes 10–40 and five colors)

20. A pair of capri leggings because they're your go-to when you're at home, so why would you leave them behind? You can wear them with all the tops in your bag *and* if it's cooler than you anticipated, you can wear them under your pants for added warmth.

Lane Bryant

Price: $49.95 (available in sizes 10–40 and three colors)

21. A Bermuda short in a crisp white that you'll still be in love with when you look back over your photos from the trip, weeks after you get home.

Lane Bryant

Price: $79.95 (available in sizes 12–40)

22. A checkered purple shirt giving cornfield chic when paired under your overalls. It's just a fun and flirty top courtesy of the ruffled sleeves. And who doesn't like a mock neck?

Lane Bryant

Price: $23.49+ (available in sizes 12–28 and three styles)

23. A cinched waist, hooded dress for casual days, strolling along the shoreline, when suddenly you spot that cool person you met the day before. They suggest you take a dip with them in a nearby lake, and thankfully, you're already wearing your swimsuit underneath your dress.

Lane Bryant

Price: $39 (originally $69.95; available in sizes 10–40 and two colors)

24. A square-neck maxi dress here to ensure you stay fly for whatever your trip has to offer. You can pair it with any shoe you brought, the sneakers or the sandals, and layer a collared shirt on top for cooler sunsets.

Lane Bryant

Price: $29+ (available in sizes 10–40 and two colors/patterns)

25. A classic denim jacket — the perfect *all-covering* for every outfit you pack. And, if you wear it on the plane, you can free up even more space in your carry-on.

Lane Bryant

Price: $49 (originally $99.95; available in sizes 12–40)

26. A boat-neck tank with a fun abstract design that can match your white leggings and your denim shorts while offering a bit of flair to your otherwise neutral packing list.

Lane Bryant

Price: $39.95 (available in sizes 10–40 and 10 patterns)

27. A pair of wide-leg linen pants that is both your fancier dress pant option and also your loungewear for happy hotel days when the adventure bug isn't biting.

Lane Bryant

Price: $79.95 (available in sizes 12–28 and seven colors and patterns)

Some reviews have been edited for length and/or clarity.