How I Fit Over 250 Outfits in a Carry-On

Yes, that’s over 250 outfit options from fewer than 20 pieces. On my flight out to Iceland, my seatmate couldn’t believe the carry-on backpack I slid into our overhead bin was my only piece of luggage. And I have to admit, breezing straight past the baggage claim crowd at Keflavik as all those red-eye flights poured in felt really good.

I’ve spent months upon months finely tuning my packing list to balance traveling carry-on only, covering multiple seasons, and staying at least semi-fashionable part of the time. You can decide for yourself whether that’s an art or a science – I’m just happy to lead by example.


Table of Contents

My Bag

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I carry the Osprey Farpoint 40 Backpack, though because I’m petite I have the small size, which is technically only 38 liters. Inside, there’s one large main compartment with one internal mesh pocket on the bag’s “lid.” A front pocket includes another smaller mesh pocket and a laptop sleeve. There’s a small top pocket and two external mesh pockets on the pack’s front. There are also two sets of compression straps, one in the main compartment and one outside the pack.

When full, the bag measures 20 inches long, 14 inches wide, and 10 inches deep, which fits within most airlines’ carry-on requirements. While it may not always pass the stricter carry-on regulations of some ultra-budget airlines, it is small enough to fit comfortably on my five foot frame and light enough for me to lift it over my head without difficulty.

How I Pack

I use two 10L Sea to Summit compression sacks to organize my clothes and save a little space – one for cold weather clothes, and one for warm weather clothes. I roll each piece as tightly as I can, and squeeze all the extra air out with the compression sacks. A 10L sack can pretty easily compress down to 5L, meaning my clothes take up only a quarter of my pack’s volume. It’s worth noting, however, that packing more densely saves space, not weight.

When full, my bag weighs about 25 lbs. If I’m on a super budget airline with ultra-low weight requirements, I may still have to check my bag.

I pack other items vertically in the main compartment, so most of the bag’s actual real estate can be reserved for those compression sacks full of clothes. Naturally, I wear at least a few items in transit, and I try to choose bulkier pieces and layers to save room and weight.

The Clothes

2 t-shirts – one black, one teal
2 tank tops – one black, one light blue
1 long sleeve shirt – fuchsia
1 cardigan – black
1 pair shorts – khaki
1 pair jeans
1 pair convertible hiking pants
1 pair leggings – brown
1 maxi skirt – black patterned
2 sundresses
long sleeved dress
3 pairs shoes – sneakers, flip flops, flats

Total: 18 pieces

The Math

I start with five basic tops and bottoms, all of which mix and match. One pair of pants are convertible and can also be worn as shorts or capris, so really I have seven choices for bottoms. My swimsuit is conservative, so the top can easily be worn as a regular shirt, giving me six total options for tops. (6 x 7 = 42) I also have three dresses. (42 + 3 = 45) I have three pairs of shoes which can be worn with nearly any outfit. (45 x 3 = 135) Finally, any outfit can be worn with or without a cardigan. (135 x 2 = 270)

There are some exceptions, and this also doesn’t include accessories. I do carry a lightweight sarong (which doubles as a scarf) and a few pieces of inexpensive jewelry.

Granted, the difference between some of these outfits is splitting hairs. For many of them, however, one or two simple changes can create a totally different look. There’s a definite shift between wearing a tank top and shorts with flip flops, to the same outfit with sneakers and a cardigan instead.

The Outfits

Click through the slideshow below to see all 252 possible combinations of my carry-on only packing list. For more detailed views of each outfit, visit


How My Packing List Changed

No packing list is perfect, and neither is any traveler. I actually left my cardigan at home when I left for my trip! I did replace it within a couple weeks, but it was the first of many changes to the contents of my bag. The outfits I detail above remained the core of my wardrobe. But here are a few ways my clothing changed over the course of the year.

  • As mentioned I replaced my cardigan once. I also replaced one t-shirt, and replaced my pair of jeans. Make sure you budget for wear and tear!
  • I lost my flip flops… twice! I spent a couple months looking for the same pair of Crocs, because I seriously love them, and when those got lost too, I finally gave up and grabbed a crappy pair of thongs for $2. So whether or not my bag actually had flip flops or not varied.
  • I added a second long sleeve tee and a sweater. I didn’t plan to visit London, but when I wound up there for the entire month of October I needed clothing that was both warmer and looked nicer. The long sleeve tee I wound up hanging onto. The sweater I kept until my boyfriend joined me in Nepal the following month, and after our trek, I had him take it home so it wouldn’t eat up my bag while I stuck to warmer countries.
  • I added a second pair of leggings. I asked my boyfriend to bring an extra pair for layering on our trek in Nepal, expecting to send them back home with him at the end of the two weeks. I wound up keeping them in my bag and I’m so glad I did. I like my brown capri leggings a lot, but a pair of basic black leggings wound up being much more useful for layering under dresses.
  • I added a third sundress. In Nepal, I took advantage of a hotel’s laundry service but totally failed to ask when my bag would be ready for pickup! With a nicer dinner out on the schedule before my laundry would be clean, I ducked into a souvenir stand in my PJs to pick up a dress that wound up getting a lot of wear in Southeast Asia.
  • I added a pair of elephant pants. Yes those pants that every lame-o backpacker picks up in Southeast Asia. I’m not sorry. They’re lightweight, but conservative, and the elastic at the ankles means no pesky mosquitoes finding their way up your leg. I wore them mostly for pajamas, and days I was just hanging around the hostel working on the blog.
  • Because I had to interrupt my trip to care for my dying grandfather, I was able to pack separately for my final month on the road, only taking what I would specifically need for two weeks in Peru and one week in Mexico. It wasn’t radically different to my main RTW list, but I did pare things down slightly.

In spite of a few additions, I stayed able to fit everything inside my carry-on backpack. The trick was sticking mainly to lightweight items that could roll up tightly. When I needed something bulkier, like a sweater, I made arrangements to send it home once I no longer needed it.

Packing light doesn’t need to be scary or unstylish! By choosing a few practical pieces you love in a small color palette, you can fit an entire working wardrobe into a single carry-on.

What else fits in my carry-on? Check out my full RTW packing list

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How I Fit 250 Outfits into a Carry-On

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  1. The clothing is for super skinny 12 year olds. What about us Curvy Grannies? Please post something for us that isn’t frumpy but up to date and makes us looks glamorous.

    1. As a travel website rather than a fashion site, this post is really about the method of packing, which can be applied to whichever specific items of clothing you prefer. I have included examples from my own (adult woman over 30) wardrobe, but they are just that: examples. Not prescriptions. If you are looking for a fashion website that offers specific outfit recommendations for older women, I recommend Senior Style Bible or Chic at Any Age.

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