The countdown to a holiday is all fun and games until it comes time to pack, at which point it feels more like an algebra test full of equations we didn’t prepare for.  We want to pack lightly, but we don’t want to get caught in the same outfit every single day—now that’s a tricky balance to strike.  But with a lot of determination (and a little creativity), we finally came up with a packing list that fits over 25 outfit combinations inside a carry-on suitcase.  The good news is that our formula allows for plenty of personal style expression. An essential element, of course.

The trick is to pack your bag with extremely versatile pieces that can each be worn over and over again while still looking fresh (and photo-ready).  With less than a dozen items on our packing list, we promise there will even be plenty of space left over for all your new purchases (very important).  Ahead, we show you how to style our 11 warm-weather vacation essentials so you can travel light and in style.

Item 1:

A Classic Button-Up, 3 Ways

Though a classic shirt may sound like it’s a better fit for the office, this clothing item actually offers a ton of potential while in transit to the beach, too. Wear it on the flight with jeans, again during the day for an activity that’s casual but still makes you look put together (perhaps with a pair of shorts), and then dress it up for an evening with a midi skirt and heels. You can also make it more fun by turning it into an off-the-shoulder shirt.

Item 2:

A Pair of Jeans, 3 Ways

Instead of going for a bulky pair of sweats, wear your most comfortable pair of jeans on the airplane. Simply tuck in the aforementioned shirt, and voilà. Not only will jeans keep you warm on the chilly plane ride, but they’ll also come in handy once you reach your destination. Wear it to a casual dinner and night out with a statement top and heels, and then again under a lightweight shift dress if it gets chilly in the evening.

Item 3:

A Pair of Shorts, 3 Ways

Pack some jean shorts or some casual linen ones if that’s more your pace. You can either wear it with your casual shirt or throw on a dressier top to make the look evening-appropriate. Or just throw them over your bikini bottoms for a quick change to and from the beach.

Channelling Tobias Fünke.

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Item 4:

A Wrap Skirt, 2 Ways

A wrap skirt is a perfect staple to throw in the mix because it’ll freshen up one of the shirts that you’ve already worn. You can also dress up a one-piece swimsuit by treating it as a bodysuit and wearing it tucked into your skirt either at a lunch spot on the shore or during a dressier dinner.


Item 5:

A Large Scarf, 5 Ways

A large scarf is quite possibly the most versatile piece in your closet (yes, including your jeans). Use it as an accessory by tying it around your wrist, purse handle, or head so you can add character to a lackluster outfit without much hassle, or use it as a sarong at the beach. If you feel like getting extra creative, transform your scarf into a halter top with your jeans.


Item 6:

One Pair of Heels, Infinite Ways

Heels take up a ton space in your suitcase, so if you can cut back on how many options you bring, it’ll be a much lighter load to carry. You’ll also have more storage space, which we all know is code for shopping. If you love neutral clothing and brought primarily understated pieces, consider bringing fun statement heels.

On the other hand, if you have a ton of printed separates and you’re worried about matching everything together once you reach your destination, then bring your neutral heels. If you do this, either way, your shoes will look completely new each time as long as you switch up shapes and colour schemes.


Item 7:

One Swimsuit, 4 Ways

Before you think we’re cheating with this item on the packing list, hear us out. If you opt for a bikini during your first two days of the trip, then a full piece swimsuit can actually wriggle its way into a few different outfits. Wear it with a midi skirt during the day or out on the town with your jeans when the evening begins to cool off. By the time you actually wear it to go swimming or lounge by the water, it’ll look like a brand-new item.

Item 8:

One Straw Purse, Infinite Ways

If you bring your straw purse with you as your second carry-on, you can also use it as a beach bag during the vacation. Not only will it make room for other items in your carry-on (like an evening clutch), but it will also stop you from misplacing your belongings (especially if you’re not used to switching back and forth between bags). Plus, you can have all your things with you at the beach instead of having to carry your books, cameras, phones, and whatever else in your arms to and from the sandy shores.

Item 9:

One Dressy Top, 2 Ways

If you’re running out of space in your carry-on, it could be because you have too many going-out tops packed. Since you’ll be using your casual button-up or polo, one-piece swimsuit, and your scarf as a makeshift halter as a shirt for three nights during your trip, then you really only need one more top to diversify things. A simple slip tank will be really easy to pack since it doesn’t take up much space, but go ahead and throw in your favourite ruffled off-the-shoulder top too. Opt for a material that packs well and is super compact, like silk.


Item 10:

One Pair of Flat Sandals, Infinite Ways

Though these aren’t the most exciting item on the list, they’re definitely necessary. The good news is that flat sandals are super easy to pack, so you may even be able to bring an extra item of your choice. Just make sure you’ve already broken in the shoes you pack so that you can walk around and explore while you’re not out on the water.


Item 11:

One Shift Dress, 3 Ways

A dress may seem like it only offers up one outfit option, but the trick is all about how you choose to layer it. Take a semi-sheer cover-up, for example. You can wear it during the day over your swimsuit, but then you can you layer it with jeans and heels later in the evening for a classic day-to-night look.

The length will bring in a bit of drama, and you’ll stay warm in case the temperature drops. If you choose to bring a linen button-up dress, just unbutton the bottom half so your jeans are exposed. Or if it’s a shorter shift dress, practice your half tuck and turn it into a tunic with your casual shorts.


Photo Credit: ohhcouture