How to Pack for Key West in a Carry-On

Weekender: c/o Carolina Dandy

Confession: I am a chronic over-packer. Going on a trip for 3 days? Pack 15 outfits. (A girl needs options!) I always have way too many pairs of shoes, and a whole lot of clothing that doesn’t see the light of day! So, for my trip to Key West I decided that it was time to change my ways and pack for the trip in just a carry-on. Considering we will be in bathing suits, sundresses, and sandals the whole time, it didn’t seem necessary to pack all that other “stuff” that often finds its way into my luggage. So, with my goal in mind I came up with the following five tips to help streamline my packing!

ONE // Roll Your Clothes 

My #1 tip for saving space (or in my case, squeezing a few more things in) is rolling your clothing. I usually fold the item in halves or thirds depending on what it is, and then starting at the top tightly roll it up. You will be amazed at how many more items you can get in your suitcase this way AND it helps to prevent items from wrinkling! #Bonus #Winning

TWO // Streamline Your Shoes

When heading to a tropical island, one doesn’t really need a ton of footwear options- let’s be real, I’m going to be living in flip flops and sandals. So, I decided to stick with neutrals (since I pack bright clothing) and went with a pair of Jack Rogers Georgica Jellys for the pool/beach, Sam Edelman gold Gigi sandals for touring/brunch/etc, and nude huarache heels for our nights out. I’ve got a pair for everything AND by wearing my Gigis on the plane I ended up only packing two pairs of shoes! 

THREE // Layout Clothes By Day

As I was packing I laid out my outfit by activity per day I would be wearing it. I have tons of dresses I wanted to pack, but they weren’t necessarily compatible with what we’d be doing (i.e.: boating). By thinking through what and how I would wear each outfit, I was able to make sure I was truly packing items that would be worn.

FOUR // Pack Limited Accessories

When I got out at night I always have a clutch (how perfect is this grapefruit one I found?!) but rather than packing a different color clutch for each outfit, I packed a statement piece and a neutral gold one that would match everything. This ensured I wasn’t wasting space with pieces I was never going to use!

FIVE // Mix and Match Your Looks

My final tip is to think through how you can mix and match the pieces that you are packing to create new looks. For instance, I’m packing a solid black bikini bottom and two different tops to pair with them. I’m also packing white shorts (not pictured) and three easy tees to mix and match that will give me several different looks! Shorts are bulky, but tanks are not, so packing more tops and less shorts saves space!

I hope these tips were helpful and have give you some ideas for streamlining your packing on the next trip you take! From one over-packer to another… it can be done y’all! 🙂


My Dress: c/o The Mint Julep // Striped Weekender: c/o Carolina Dandy // Striped Peplum Tanks: Old Navy // Grapefruit Clutch: Mudpie Gifts // Blue & Eyelet Dress: Wyatt via Bluefly // Striped Dress: Target // White Sandals: Jack Rogers Georgica Jelly // Gold Sandals: Sam Edelman c/o Shopbop // Hurrache Sandals: Target // Pink Tee: Lilly Pulitzer “Betsey”

If you have any other tips for packing (or fun things to do in Key West) leave me a note in the comments below!

Happy packing 🙂

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  1. May 4, 2016 / 1:28 pm

    I am awful at packing but I did pack in a carry on once when going to California for 4 days!

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