How to dress and pack for a long-haul flight

You know what's hard? Dressing for a long haul flight to a country in a different season on the other side of the world. You know what's harder? Trying to do so whilst looking stylish AND being comfortable.

I've done a fair bit of trans-hemispherical travel in my time and I feel it's time to correct the misconceptions about what you can and can't wear whilst travelling. I've seen some highly impractical 'style guides' for travel and I sense the writer's have never lived in New Zealand and had to fly for a whole day or five to get pretty much anywhere. Hmm... :) Here are my rules and I back them 100%. Save them for your next big trip!

You shall not wear jeans, skirts, or ballet flats whilst flying long-haul. Why? Because jeans don't breathe and get stinky (and they hurt). Skirts are going to leave you with icicles and stalactites where your legs should be. Ballet flats are going to literally cause your feet to drop off from the freezing aircraft temperatures. Also forget jewellery. Really - the pain of setting off the metal detector and getting treated like a terrorist suspect is just not worth it. 

Here's what I'm wearing on our flight to NYC (around 20 hours of travel). We are starting in Winter, and flying into Summer. You can reverse this if you're going the other way. 
Keep in mind that flights are always air-conditioned and slightly too cold especially when you're not moving.

What to wear on a long-haul flight - Amy MacLeod - Five Kinds of Happy

  • Jeggings (leggings that look exactly like jeans but aren't. Saving my life!). Comfier than jeans, but more decent than plain leggings.
  • Long cotton t-shirt - comfy and the fabric breathes. I like it long enough to cover my legging-butt.
  • Warm cosy jumper - I chose a plain colour and style that I'll wear at the destination too.
  • Scarf doubles as a blanket on your (always cold) flight.
  • Watch lets you keep track of time without digging for your phone.
  • Trainers are the bulkiest shoes you'll be taking and will keep your feet warm, unlike flats.
  • Circulation socks - will save your LIFE and keep you feeling comfy with no calf-pain. Amazing!
  • 1 carry-on bag + 1 small clutch with cross-body strap for documents. Easy to get to!
  • Jacket for an extra layer and makes your suitcase lighter.

In your carry-on bag:
I try to take a smallish carry-on so I can keep it on the floor infront of me rather than push past people to get to the lockers. You can take a large one but keep a handbag separate for the flight.

What to wear on a long-haul flight - Amy MacLeod - Five Kinds of Happy
  1. Warm socks, if you aren't already wearing them, to put on during the flight.
  2. Cosmetics etc in a clear bag. I've found even powder foundation can set off the liquid-detectors so now I just chuck it all in the clear bag.
  3. Extras like tissues and gum so you can stay fresh. Also I like to have drops such as Vicks to help with the ear-popping. Earplugs and eye-mask are helpful too.
  4. A small clutch with strap for your documents, that can fit inside your other bag if needed. Keep in mind you will need your passport number during the flight.
  5. A black skirt, folded up. Mine folds up tiny. It will be used when you land (see next step).
  6. A notebook and pen. 
  7. Flat shoes that go with your skirt. I like ballet flats as they are easy to stuff into your bag and will be appropriate for anywhere.

So how does it work when you arrive at your destination?

The quick switch (in the airport toilets when you arrive...)

What to wear on a long-haul flight - Amy MacLeod - Five Kinds of Happy
You slip into the skirt and flats, stuff away your jeggings and socks (yay for easily squishable clothing) and you're off to collect your suitcase from the luggage belt and saunter outside into tropical conditions.
Sunglasses are optional depending how red-eyed and haggard you like to appear in public... ;)

If you're travelling from Summer to Winter, just reverse this process.

I MAY have a few outfit posts coming up over the next little while. I know it's not something I've done much of here so I'm a bit wary of jumping in and talking all about clothes when y'all want to see some interiors. But it IS supposed to be 5 different kinds of happy, and outfits kinda make me happy too. Of course, this all depends whether I can get good pictures whilst in NYC, and from experience I tend to stress the husband out with my photographic demands ('You're making me look all pastey! Stop angling the camera down and making my legs looks stumpy! Why didn't you tell me my hair was doing that?' etc...)

What are your experiences of long-haul flying? Maybe you have your own tips? I'd love to hear!


  1. These are such great tips. I always have to take a sleeping pill for sure.

  2. Reversing the idea is great, but my mind is blank. We leave NZ on New Year's Day, spend the evening in Seoul with friends and then fly on to London. Jeggings sound great but on my 57yr old backside!!!! Any brilliant suggestions would be greatly appreciated.

  3. this is such a great tip! but what do you wear when traveling in the other direction (summer to winter)?


Thanks for your comment. You are awesome!