How to Pack a Carry-On for a 5 Day Trip

I always overpack. For vacations, for day trips to the beach, for an overnight to my parents house. I always, without fail, pack more than I need to. Which is usually fine, when I’m taking my own car & can just throw all my crap (extremely vital belongings) into the back. This becomes a problem when I’m flying to my destination. I tend to fly on airlines where the first bag is free, but a full size piece of luggage for less than a week? Over the years I’ve begun to feel like this is a bit much. So I’ve tried cutting back on what I bring. But I’m a girl! There are so many more things a lady needs to pack for a trip than a guy does! (Can I get an amen?)

I recently went on a trip to New York City for 5 days. Well, 3 days, with 2 flying days on either end. The airline we were taking also charged for any checked bags. So I really wanted to fit all my stuff into a carry-on sized bag, & I didn’t plan on doing a ton of shopping, so I figured I could do it. But this was different than when I packed a carry-on for my week long trip last summer…all I needed then were a bunch of sundresses, bathing suits, & some shorts & t-shirts. Since I wouldn’t be spending the entire time on a beach, I needed real clothes.

Now, I still overpacked, but significantly less so. There were only a few pieces that didn’t actually get worn (had I paid more attention to the weather, I could have cut out some things, probably the shorts & the denim jacket. I didn’t wear the white dress, but my sister did, so I was glad to have it. What can I say? I wanted to wear my cute warm weather stuff!) I had an outfit for each fly day, as well as 2 outfits for each day in NYC – one for exploring during the day, & one for the Broadway shows at night. (So technically it could be seen as a week long trip…moving on)


(pictured: most of the clothes I took)


(Pictured: flats, sandals, pj pants, denim jacket, jewelry box, dress worn on first flight)

(Note: the black & gray shoes, workout shorts, & the black sweater on the right were not taken.

Not pictured: white coat (in my soft carry-on), gray shorts, unmentionables)

Here’s what I took:

2 pairs of jeans

Plaid shorts

Black pencil skirt

2 nice tops for Broadway

White sundress

Cropped cardigan

Denim jacket

Purple cardigan

Black tank top

Black tee

4 camisoles (varying colors)

Gray tee

Pj top

Pj pants

Socks (4 pair)

Unmentionables (3 bras, 6 unders)



I know this may look like a lot for 3 days, but it worked out to just what I had planned: 2 fly outfits, 2 outfits per day, & 1 extra in case I spilled something or didn’t feel like wearing an outfit I had already planned. Now…how did I fit all of this??

The Rolling Method

I was a little skeptical about this at first, but it really is helpful. I actually put all my clothes in the suitcase as they were folded (in the first picture) & it filled up pretty quick! It was just about full before I even had my shoes, toiletries/makeup, or last minute clothes. It was still a tight fit with the rolling method, but I was able to fit everything much easier! And I didn’t have to cut out things just so I would have room. (You can see my denim jacket & pj pants are rolled in the second picture.)

This is a great alternative to regular folding, because with rolling luggage, you always run into those bars on the bottom of the bag. When your clothes are rolled, they can fit between the bars, instead of leaving it as unused space. It may not seem like it, but it is a significant amount of extra packing area, especially if you can never make up your mind on what to take love all your clothes equally & want to take them all!

The Bundle Method

Another method to use is the bundle method. I tried this when I first packed my bag. Some people prefer this, I found that it gave me less room to cram, so I did not do it for my trip home. With the bundle method, you stack all your items, then fold & roll together, as seen pictured below. While this keeps all your like items together (shirts, pants, etc), it takes up more space. I find that when I roll items individually, they are easier to cram in the nooks & crannies after I have the larger items in place.

packing3 packing4

(Left: shirts using the bundle method, before being rolled

Right: Makeup bag, toiletries bag, liquids bag (using the 3-1-1 TSA rules))


As I pack my bag, I start with the larger rolled items on the bottom. Jeans, sweatshirts, & other bulky items fall into this category. Then work your way to the smaller items. Then I move to shorts & skirts. T-shirts come after that, & camis are usually last. Because they are so small, they work perfectly to fill in the gaps & small miscellaneous areas of your bag. I always lay things down horizontally (so they fit between the bars). If you like, you can stagger your clothes. Rolling allows for this easily. Then I put my shoes & toiletry bags on top. I like having flatter toiletry bags as opposed to square bags, because I find that they pack easier. I don’t need to save an entire corner for that bag. For each item I pack, I simply lay it out, then fold it in half vertically (the “hot dog” way), & roll! It doesn’t matter if you start from the neckline or the bottom…it all reaches the same outcome. This is what my suitcase looked like after I had rolled everything & stuffed my bag full:


(Tip: Save those hotel shower caps! Use them to put your shoes in so they don’t get the rest of your clothes dirty)

This may be surprising, but I actually still had room! Not a ton, but enough for a couple t-shirts I bought on my trip. It seems packed, but there was still room to give once it was zipped. Also, my bag does not have a zippered portion on the inside of the “lid” so everything needed to fit in the main compartment. It was nice to have the extra room, so that I didn’t have to cram it in my soft carry-on (pictured below) for the flight home. In my soft carry-on, I had things like my everyday purse (which is a small crossbody), book, camera, socks (those flights get cold!), light weight jacket, sunglasses, etc. I also had room left in my soft carry-on for fragile & smaller things I bought on the trip.


Some other tricks I have learned are to pack your socks in your shoes. Most shoes don’t collapse anyway (unless they are flats) so use the space for socks, or even underwear if you want! Depending on your bra, it usually creates a little dome, so use that space wisely. I usually keep my bras & underwear together.

If you are flying, make sure to follow the 3-1-1 rule, & have the bag at the top so it is accessible when you need to pull it out to put in the bin when you go through security. Another thing to note: you are allowed to take a disposable razor in your carry-on bag. I took a 2-blade razor, but my sister had her 5- blade Venus. Neither one of us had problems getting through security. (NOTE: This information was found on the TSA website,, but always remember to check for updated information on which items are allowed. DO NOT rely on this post for accurate, up to date information)


So that’s all I took! One carry-on piece of luggage & one “purse” to stow under my seat! And ZERO baggage fees! SUCCESS!

By Guest Blogger Ariel Justice

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