20+ Outfits and Two Weeks in One Carry On: How I Did It

I challenged myself to travel for two weeks to four different countries using only one carry-on. I almost talked myself out of it three times, but now that I’m back? I’m never over-packing again. Checking luggage can be an expensive pain in the rear and one that I don’t want to have to deal with if I don’t have to. I was convinced that I would look like a frazzled frump if I kept my clothing options to things that could fit in a carry-on. But with the help of friends, Pinterest, and the Internet I managed to look pretty good for the entire two weeks at the beach and on the sea.

Could I manage two weeks in one carry-on in winter? It would be harder, but you’d better believe that I’m going to give it a try if I ever get the chance.

Here’s what my trip entailed, five days staying at a hotel in Sarasota, Florida followed by an eight day Eastern Caribbean cruise. Activities included zip lining, hiking, kayaking, snorkeling, and plenty of time on white sandy beaches. There were nice dinners, casual lunches, and really casual breakfasts. I kept toiletries to a minimum by bringing items that could multitask and buying bigger items (sunscreen) once in Florida. While I did wear everything I brought (and even managed to share with my mom on the cruise), I could have brought even less.

I’m certainly no fashion blogger, I’m just an average mom with an average shape and these photos were taken by my mom on the last day of our cruise in 90 degree humid weather because I wasn’t smart enough to take a photos of all the outfits AS I was actually wearing them. You’ll notice I have duplicates of several items in different colors, because when you find what works and it’s on sale? You go with it.

  • 20+ Outfits (No Repeats!) One Carry On 1 of 16
    Carry On

    Behold and prepare yourselves for the secrets of packing prowess.

  • What’s In The Bag? 2 of 16
    What's In The Bag

    Whew, that's a lot of clothes!

  • The MOST Important Detail 3 of 16
    suitcase

    Don't fold your clothes, ROLL your clothes. It makes the BIGGEST difference when packing a lot of clothes into a very little suitcase. Swear.

  • The Comfy Clothes 4 of 16
    comfy

    Rather than bringing clothes that could only be used as pajamas, I brought items I could hit the midnight buffet in and not look totally ridiculous. On the right is my travel outfit, as it took up the most space with the sweater and running shoes.

    Left: Top - Wet Seal, Bottoms - Disneyworld (yay, Minnie!)

    Right: Top - Moving Comfort, Sweater and 2 in 1 Leggings - Athleta, Shoes - Reebok

  • Casual Outfits Round One 5 of 16
    five

    You're going to notice I went with a theme on this trip, coral, white, and blue. Even back home I do my best to make sure everything I buy goes with at least six other things I already own — which made packing for this trip even easier.

    Shirts and Shorts - J. Crew Shoes - Nordstrom Rack

  • Casual Outfits Round Two 6 of 16
    six

    The blazer took up the most room, but made the most difference when it came to dressing up an outfit. It also helped that it was linen, so it didn't really matter if it was a little wrinkled. Any jewelry I brought also went with multiple outfits and followed my theme.

    Shorts, blazer and white button up - J. Crew, Lace shirt - Madewell, Shoes - Nordstrom Rack

  • Casual Outfits Round Three 7 of 16
    one

    The bright colors really helped me feel like I was wearing outfits instead of clothes. I had originally planned on going with more black but I'm glad I didn't.

    Maxi dress - Athleta, Shirts and white shorts- J. Crew, Crop Trousers - Anthropologie, Shoes - Nordstrom Rack

  • Casual Outfits Round Four 8 of 16
    three

    Linen and cotton forever. The linen looked good even when rumpled. (Not to mention how comfortable it was in the heat.)

    Lace Top - Madewell, Crop Trousers - Anthropologie, Shirt and Bermuda Shorts - J. Crew, Shoes - Nordstrom Rack

  • Casual Outfits Round Five 9 of 16
    two

    I kept my shoes to a minimum by wearing my largest ones on the plane and keeping the others small and simple. I had a pair of white sandals, black sandals (that could be dressed up or down) as well as a pair of comfortable flip flops for trips to and from the pool or beach.

    Left: Top - J. Crew, Bottoms - Anthropologie Right: Top - Madewell, Bottoms - J. Crew, Shoes - Nordstrom Rack

  • Laundry Break 10 of 16
    laundry

    I did to laundry on the ship once for the bargain price of $7 to wash and dry one large load of Addie's and my clothes. I brought a lingerie bag for my dedicates as well as one of those little soap pacs and a dryer sheet. (No need to pay another $5 for soap on the ship.) I also had a wash and stain laundry soap bar for spot washing in the sink and a little spray bottle of Febreze for my casino scented clothes.

  • Casual Outfits Round Six 11 of 16
    four

    I cannot say enough nice things about the Perfect Fit Shirt and Schoolboy Blazer from J. Crew. Yes, they are pricey but I will wear them forever and they *fit* me, amen.

    Tops, blazer and shorts: All J. Crew, Shoes - Nordstrom Rack

  • Swimsuits 12 of 16
    swim

    These right here could be (and probably will be) an entirely different post. I am a 32F and finding swimsuits to accomodate my petite height and proportions that also accommodate my huge boobs? IT'S NOT EASY. I finally found these bra sized swimsuits and THEY HAVE CHANGED MY LIFE. I played in the water all day and never once did I have a nip slip. Unheard of. (Not to mention I could wear a suit under clothes or coverup and not feel like I was flopping and sagging all over the place.)

    Left and Center: Panache, Right: Next by Athena

  • Coverups 13 of 16
    coverups

    I thought coverups were stupid, until I bought one. Now if I'm going anywhere I'll be swimming I bring a coverup (or two) with me. They're great for running in and out of restrooms, restaurants and shops where swimsuits are not proper attire without getting your real clothes wet or chlorinated. They're also a great alternative to a soggy towel wrapped around you on your way to or from the pool on a cruise ship or in a hotel.

    Basically coverups scream vacation and serve a very worthy purpose.

    Left: Macy's Right: Target Shoes: Børn

  • Gym/Active Outfit 14 of 16
    gym one

    I am addicted to cute, functional and well fitting workout clothes. They make a huge difference in my motivation to work out and my confidence while I am working out. Hey, it's my thing. It's also great to have functional and well fitting athletic wear during really strenuous activities (kayaking, hiking, and zip lining were all included on this trip.)

    Top: Ellie Bottoms: Athleta Shoes: Reebok

  • More Gym/Active Outfits 15 of 16
    gym two

    I'd like to also proclaim my love to the skort and to these Reebok shoes. The skirt/legging combo is basically the best thing to ever happen to me. All the comfort of leggings without my rear end hanging out, and skorts? Way more comfortable than shorts (I hate feeling like people can see my underpants when I sit down.) Plus, I feel fancier in skirts compared to shorts, so there.

    The shoes? They're Reebok ATVs but I call them my frog finger shoes. They're meant for trail running and different terrains. I tested them on every terrain from tightropes to sandy beaches and they did not disappoint once. I have always thought of Reebok as kind of a lame shoe, but these have changed my perspective entirely (they got lots of compliments too!)

    Left: Top - Moving Comfort, Bottoms - Athleta, Middle: Top - Ellie, Skort - Athelta, Right: Top - Athleta, Skort - Moving Comfort

    (Disclosure: I did receive the Moving Comfort Pieces as well as the shoes for review purposes. All opinions on them are my own and my opinion is two thumbs up on all of it.)

     

  • LBDs 16 of 16
    LBD

    If you've ever gone on a cruise then you'll know there are cruise elegant evenings, for some people this means putting on a shirt, for others elegant night means tuxedos and ballgowns. I fell somewhere in the middle on this trip, I love dressing up but couldn't sacrifice the space to a dress and heels I'd wear once or twice. Again, jewelry and the blazer fancied up a couple of plain and packable little black dresses well enough.

    The dress on the left is the Nectar dress from Athleta and every traveling woman should have one. It never wrinkles, can double as a swim cover up, dries super quick, fits amazingly well and can be washed in a sink and dry within hours. The photos here don't really do it justice (darn wind) but if there were one piece I would tell you to get? It's this dress. (I bought mine in the tall length since I don't love my knees and thighs showing.) There is also a Nectar 2 dress but it fits more like scrubs than a dress.

    Blazer: J. Crew, Right: Dress - Target, Shoes - Nordstrom Rack

Find more of Casey’s writing on her blog moosh in indy or her Babble Voices site Shutterlovely. She’s also available on twitter, facebook, flickr and Instagram. If you can’t find her any of those places? Check the couch, she’s probably taking a nap.

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