The Obsessive Planner’s Guide | Packing Your Carry-on

So you plan a weekend-4 days-week long trip And, like me, you hate to check luggage. You pull out your pretty carry-on–durable and pragmatic or bright and colorful, maybe it even makes a statement. But you pull it out, and then…what?

You freeze. You freak out. How in the world am I going to back a weekend-four days-week long trip all in my carry-on?

Don’t worry, I’m your obsessive planner. I help scare those worries away by planning so far ahead that all you have to do is search Google and read. I’ll admit, I’m not a pro, but I’ve managed to pack more than enough into a carry-on and personal item (thanks Southwest!). I don’t recall landing in a new location thinking, If only I’d had more room… So, I’m going to give you my tips to packing smart and I think they can help.

1. The Rolling Method

photo of carry on luggage with clothing insideCaution: outfit combinations in the carry-on number more than they appear! And yes, that’s make-up mirror.

I packed six different outfits using the rolling method. That doesn’t include exercise wear or sleep-wear. I mean five, completely different top/bottom combinations and a dress. Roll tightly, and pack loose clothing in the summer. Winter months become a little harder since winter clothing is thicker, but still possible. I would also suggest to roll your shirt with the bottoms; only slightly thicker, but saves a lot of space.

I have used the rolling method for years (thanks Daddy!). Not just for packing a carry-on, I also roll my clothes in my dresser drawers, but that’s another post, for another time. I don’t roll underwear or bras (I’d love to see the woman who managed that!). Ideally, you should store them in a closable compartment in the carry on. I have a mesh compartment not pictured on the opposite side of where I pack clothes. Underwear, bras, sleep-wear, and exercise wear goes inside.

Light jackets, coats, hoodies? I fly in those. A bit of a nuisance when going through security (or, just get TSA pre-check!) but jackets take up too much space. However, if you prefer to pack it, lay it over the very top of your packed items.

2. Pack Shoes That Pair with Multiple Outfits

photo of flip flops with caption that reads, "shoes," carry on
The padding in the soles? I can’t walk in flats without cushion. (arch problems)

I never pack more than 4 pair of shoes, including my go-anywhere Nike flip-flops. My go-to colors: a neutral pair (black or white, never both), a shimmery pair (gold, silver, copper, rose gold), and one POPping color. Yellow has quickly become a personal favorite since it pairs with so many outfits. But feel free to try red, turquoise, orange. Have fun with it. In cooler months, I pack baby-doll flats instead of flip-flops. And boots? No more than two pair of flat boots. Anything longer than ankle length, I roll. I always fly in my tennis shoes. Typically, the thickest shoe so I wear them on the plane.

Despite owning several pairs of heels, I very rarely pack them. If needed, because seriously, sometimes you need a good heel, I pack one pair. With all heels and baby doll flats, I tuck each shoe into the other. Keeps the shape and they lay flat.

two pairs of shoes for a carry-on two pairs of shoes tucked into each other for a carry on









3. Ziploc Bags are Your New Bestie

jewelry in ziplock bags, labeled, "necklaces" and "earrings," carry-on

Okay, so clearly I love jewelry. You should see my collection. Needless to say I MUST have colorful combinations when I travel. Jewelry packs into quart, pint, or snack size Ziploc bags with ease. They are waterproof! You can label them. And, cheaper than those cute little containers or bags at your favorite retail beauty supply store. Bonus? Ziploc bags fold, mold, and squeeze into whatever space you have.

I’m OCD so I even split my thin necklaces from bulky, stud earrings from dangling. But you don’t have to. Clearly you can pack a month’s worth of potential jewelry combinations in 2 bags.

If you’re not as much of a jewelry hoarder as I am, Ziploc bags also work for hair ties, bows, hair pins, rubber bands, underwear, writing utensils, business cards, pretty much anything small and loose. And of course, your required liquids (which I’ll get into later).

packed carry-on
Bag still isn’t full!

4. Travel-Size EVERYTHING.

“Everywhere I travel, tiny life. Single-serving sugar, single-serving cream, single pat of butter. The microwave Cordon Bleu hobby kit. Shampoo-conditioner combos, sample-packaged mouthwash, tiny bars of soap. The people I meet on each flight? They’re single-serving friends.”  _Fight Club

photo of travel size items with label, "toiletries, cosmetics/hairWe all know that TSA airport security rules restrict traveling with liquids, gels, creams over 3oz. So travel size grew in popularity. But, the other plus of travel size? It’s TINY! Talk about a space saver. Travel size loofahs, travel size perfume, even travel size eye shadow and foundation. I love it. Allows me to still bask in my desire to always smell good and paint my face and still save space.

Several stores sell your favorite scents and lotions in travel size under 3 oz. However, another tip? Your large department stores (i.e. Wal-Mart) sell plastic travel size containers–spray bottles, squeeze bottles, pill containers. I use these to transport scents that never come in travel size, oils and sprays for my hair.

My clear bag? Two different lotions, 2 perfumes, a set of contacts, toothpaste, toothbrush, oil for my hair, baby oil for my skin, deodorant, and shower gel.

photo of packed carry-on bagI’m a bit of a glam woman so I pack eye shadow, highlighter, primer, lipstick, lip and eye liner, and make up brushes. And they do go into actual cosmetic bags. Right on top. Usually the very last thing I pack before the top layers go in.

5. Load Pliable Items on Top

fully packed carry on
Yes, those are rain boots.

Scarves, hats, bras (if you don’t have the closable compartments), an empty purse. I packed rain boots and surprised myself. The beauty of packing some of these items? You can slide other things inside boots, inside the purse, between rolled up clothing. This would also be when you would lay a jacket over the top–though I wouldn’t advice rain boots AND a jacket. Most airlines have a weight limit.

6. Get Creative with Your Personal Item

If allowed one personal item, step outside of the box of just a purse or small bag. I’ve traveled with a book bag on more than one occasion, a large bag, even a weekend-bag. Currently, I pack most of my electronics in my personal item. I also put my clear bag with liquids in my personal bag. This way, when moving through airport security, I never unpack anything from my carry on; only the personal item.

Different airports have different policies about what you must remove. And this also varies depending on a domestic or international flight. With new laws regarding traveling with electronics, it’s important to know what you can take before you show up at the airport. So research first!

Best bet? If traveling with a laptop or large electronics, store them in a bag where you can easily access them in case you need to pull them out into a bin.


Find anything helpful in my tips? Have better suggestions I left out? I hope I could help at least one person with the knowledge I’ve gained through my travels and I look forward to my tips evolving!

pinterest pin, how to pack your carry on

Disclaimer: I base my tips for packing on the basis of one carry-on bag and one personal item. The personal item is typically larger than a standard size pocketbook.


  1. Traveling is always so exciting that when it comes to packing, I know as a female overpacking happens often. I tend to pack items that I don’t even up wearing/using. I love the rolling method because it allows more room and the fact that you’re thinking about the outfits before just throwing them in. I will be thinking more about what I’m packing and how I’m packing after reading your post. Thanks! : )


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