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 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 light, 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.


My Bag

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 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 compression sacks from Sea to Summit 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
2 pairs pants – one gray, one dark wash denim
1 pair leggings – brown
1 maxi skirt – black patterned
2 sundresses
1 long sleeve dress
1 swimsuit
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 sarong, which can be worn as a scarf with any outfit or even tied into a casual skirt, and a few pieces of lightweight, inexpensive jewelry, which can dress up an outfit.

Granted, the difference between some of these outfits is splitting hairs, but for many of them, 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.

(Confession: I planned to wear my cardigan in transit, so didn’t pack it, and of course wound up leaving it at home. I’m not sure at this point whether I’ll try to recover it or replace it, but ultimately there will be a basic black cardigan in the mix.)

The Outfits

Click through the slideshow below to see all 252 possible combinations. For more detailed views of each outfit, visit

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