In 2018 I did a lot of traveling over the weekends. PTO (paid time off) is not something I use lightly. It’s almost a craft for how hard I have to plan it out sometimes so I frequently travel over the weekends.

Long weekend travel is not a groundbreaking concept, but not paying for a carry-on or a checked bag is. Millennials are stepping up their travel game in switching out products for experiences. Airbnb CEO Brian Chesky shared research that ‘three in four millennials said they’d rather buy an experience than a physical good.”

I don’t know about you but I’m ALL about budget traveling. Get me to the new destination with the smallest paycheck. It can be done and I think millennials have really hanged the game around for the travel industry. With that being said, unless a carry on is free, I hardly ever have anything more than a backpack when it comes to traveling. I feel as if I have mastered the personal item travel hack and in doing so I’ve saved myself at least $500 just in packing fees with my 8 roundtrip flights in 2018. You know what $500 is? ANOTHER ROUNDTRIP TICKET SOMEWHERE ELSE!

So, how do you pack everything into a personal item

Your personal item carrier
Let’s look at this a little more closely. Carriers typically define a personal item as a briefcase, purse or handbag, or a laptop with a case. That is not written in stone anywhere though. From my experience, I’ve learned that as long as it fits under your seat it is a personal item. My boyfriend uses a small duffel bag as his personal item and no one has ever said anything about it because it fits under the seat.

Of course, bringing a sizeable suitcase or bags with you can be necessary, even searching “luggage storage near me” will free you of bags you don’t need right now as you get acclimated to the area, but it’s always best to simplify your essential holders as much as you can.

Get yourself any type of bag that will fit all your necessities, and still fit under the seat in front of you.


I use High Sierra’s Elly backpacks (currently only $20!) because they are spacious and have LOTS of pockets (which we will be using a little later).  No one has ever questioned my personal item choice using this bad boy.


Now let’s get into the items in your personal item vs the items on your person

The Travel Outfit
This is the bulkiest outfit of the trip. Think chunky everything and big boots.


Layering is so so important when it comes to personal item flights. Once again, this isn’t a groundbreaking idea. Layering shirts, sweaters, scarves, and jackets on the plane is a very practical and well-known move. The more you have on your body, the less you have in your bag.


Your outfit should consist of (weather permitted) a cami or under-tank, t-shirt, sweater, scarf and coat with zipper pockets. Your coat is your lifeline. You would be surprised at the amount of additional packing space a zipper coat provides you for things like chapstick, chargers, wallets and other travel day essentials.


I prefer zippers because this ensures no spillage during the security checkpoint and while taking the coat off on the plane.


On my person I usually have

• Hat (optional)
• Camisole
• T-shirt
• Sweater
• Scarf
• Jacket (w/ zipper pockets)
• Jeans
• Long socks
• Boots
• My airport crossbody (perfect airport accessory you can read about here)

You’re probably thinking you’re going to get warm. You’re not wrong. I typically run cold so this works for me but just peel layers off as you get warm and hang onto them.

The Travel Bag
Now that we’ve established what is on my body, let’s talk about what is in my bag because not a lot is left over.

Use your pockets to keep things organized

I keep all of my electronics (chargers, USB ports, cameras, and converters) in the front pocket of my backpack using the compartments as dividers and organizers. Putting them here makes them easily accessible and organized. The last thing you want is to pull EVERYTHING out because you can’t find your headphones in the middle of the terminal. 

Utilize your Side Pockets

I keep my socks and undies in my outside pockets where water bottles are usually kept. This helps me pack the correct amount otherwise I’ll go overboard on socks and underwear like I need 20 pairs of each for four days…

Plan Out Your Outfits

This sounds tedious, but I don’t mean to plan them out for each day. I mean pick color schemes that tend to go well with each other. A lot of people like to wear color but with travel, I think you have to be a little more selective and practical. I mix in a lot of greys, blacks, and khaki which are interchangeable colors. My go-to pop of color is maroon. All of those colors are easy to match, making it simple for me to create outfits without having to plan anything out in detail. Don’t forget the jewelry!

Pouches, Pouches, Pouches

Without individual bags, there is no way I would stay organized. First, I have a toiletry bag I (silver pouch pictured above) that fits my razor, loofah, toothbrush, hair extras, etc. Then I have my make-up bag (the gold glittery bag) that holds all my brushes, bronzers, and whatever else I deem necessary. I also carry a jewelry organizer pouch my nana made me. It has a ton of compartments making it practically impossible for any of my jewels to become tangled. Last I have my plastic quart-sized bag with ALL of my liquids and lotions for easy TSA access. I pack these in last so I can easily pull them out.

For Fun

I’ll pack a book, journal, or my iPad. I only pack two of the three because I just don’t have room for all three.


In my bag I usually have

• Hat (optional)
• Socks (4)
• Undies (4-5)
• T-shirt (2-3)
• Sweater or extra jacket (1-2) – girls gotta have options
• Jeans (1)
• Yoga pants (double as pajamas)
• Pajama shirt
• Sneakers
• Makeup bag
• Toiletry Bag
• Liquids in Quart size bag
• Jewelry Bag
• Fun stuff (iPad/book/journal)
• Electronic needs
• Curling iron or flat iron (always one, never both)
• Hairbrush
• Sunnies (always)

 

A four day packing list would look like this:

 

 

• 2 pairs of pants (one you wear on the plane, one you pack)
• 3 tops (one you wear, two you pack)
• 1 sweater (wear it)
• 1 pair of yoga pants (to double as your workout clothes or pjamas)
• 1 scarf (wear it)
• 4 pairs  of underwear
• 4 pairs of socks
• Weather Permitted Optional clothing items (hats, gloves- which you would be wearing)

 

 

Of that list, what is packed in your bag is only:

 

 

• 1 pair of pants
• 2 tops
• 1 pair of pjs or workout clothes
• 3 pairs of underwear
• 3 pairs of socks
• Toiletries
• Makeup (if needed)
• Additonals (sunnies, jewelry, iPad)

 

 

That fits in a personal item. Easily.

 

Essentially as long as you remember that you’re not BOUND to personal item dimensions, wear your heaviest clothes onto the plane, roll & tuck then you should have no problem packing all the goods into your personal item bag. I hope this helped you see how much of a packrat you DON’T need to be for a little weekend getaway! Baggage fees are for chumps, splurge on something else.