For plane flights, I wear comfortable pants…like jeggings, or a yoga style pant. I also get cold, so I always carry a pashmina wrap or a cashmere wrap with me. Or a fleece jacket (I have some that are blazer style). The last time I flew internationally, I put a pair of fleece socks in my carryon bag…they felt great while on the plane.
A nice scarf makes me feel sort of put together!
I freeze on long haul flights. I wear comfy jeans because they are thick. Long sleeved T-shirt with a cami under and zip hoodie on top. Then I can zip, unzip, or take off as needed.
I love the Vionic Robyn flat - it’s great for travel and great for summer walking.
Don’t take your shoes off!! On a flight to. New Zealand I took off my shoes and at the end of the flight, my feet were so puffy that I could hardly get my feet into my shoes. I ended up smashing the back and wearing my shoes like flip flops as I went through customs.
Regarding plane bathroom situation - Mr. B brings hotel slippers to slip into after take off on intercontinental flights. He throws out those slippers after the flight. You never know what you will be putting into your purse with those ballet shoes if you wear them to the lavatory.
I would wear soft jeggings, slip on shoes a la Keds, a long tee, a scarf, and a denim jacket, and change into a more summer-y outfit upon arrival.
I would avoid a wide-leg pant. It always seems to end up on the floor of the bathroom, no matter how much I try to scrunch it up. My neighbor recently started selling a line of clothes that are marketed as athleisure. I think it’s an MLM (which I normally hate), but I like the clothes, and everything I’ve bought so far.
Here’s a link to their travel collection…
https://www.discoverpeach.com/t/featured/the-travel-edit
I also do like dresses for travel…just so easy to go to the bathroom, but also need pockets, because I rarely carry a purse.
Layers are good for adapting to temperature extremes, and for minimizing luggage. I do try to wear my biggest, bulkiest items (sweater, jacket, boots), so I don’t have to pack them.
I dress as nice as I can in a way that’s the most comfortable. I like to look nice when traveling so I won’t be hassled in any way. Has worked so far.
I do wear very nice leggings-they look like Laura Petrie (Mary Tyler Moore) with a nice sandal and a very nice shirt or shirt/vest/blazer combo that can hold up and not wrinkle but that is very comfy. I bring warm socks to change into once I’m settled.
@conmama isn’t there something in your closet that you can make work and save you $$ for a clothing item you’d be excited to use before or after the trip too?
I don’t suppose the Dressing Young Loft coatigen can make an appearance on the plane… 
I usually leave my slip on shoes for the whole flight. One, my feet freeze, and two, those airplane toilets. Gross.
I have recently been flying in a maxi dress. That would work with sandals. It’s long so it cover my legs if the flight is cold. I bring fuzzy socks to wear on the plane. I pair it with a jean jacket that looks cute and has great pockets. I also have a pashmina scarf type thing that’s cashmere that I can use for a blanket or a wrap. It’s a new thing for me and shockingly comfortable (I’m NOT a dress girl irl) and really practical traveling outfit.
@abasket, LOL! Actually wore my coatigan yesterday. It was so cold outside I was comfy the whole time inside!
Yeah, I have something I could wear, it’s what I’ve been wearing on planes for years now and I’m sick of it. I know I have it, but would like something a little more updated and youthful. I know, I’m vain.
@one1ofeach , I’ve actually thought of that, a maxi dress, but I don’t think I’d like my bare thighs touching the whole flight.
I have several pairs of these
They look sloppy in the picture but are actually rather stylish. Very comfy with three front pockets - one of them with a zipper for safety. Since I’m always cold of flights I wear a pair or comfy leggings or workout capri tights underneath.
Absolutely no bra! Either a compression type tank/tee or a workout top with built in shelf bra.
depending on the destination I’ll wear booties or stylish sneakers.
Also always bring a large pashmina style shawl, a warm sweater that covers my butt (I hate the feeling of being cold in the lower back) and for longer flights - a Xanax 
Yes to maxi dresses. I have a go to dress that I always wear on flights to Hawaii. Had it for 7 years now!
Leggings solve that problem under long dresses… capri or ankle length. And if you wear leggings and a tee under a loose dress on the plane, you have the under-layers you can use with other outfits on your trip. Silk leggings and tees will hang to dry very quickly. ime.
Silk is my preferred travel fabric. Easy wash and dry. Comfortable in heat. Good base layer in cold. Wrinkles shake out pretty easily.
eta: after going overseas twice a year for a long time, I’ve lots of time to think about this question 
This is my best solution so far.
I am currently voting for the loose fitting, casual maxi dress with capri leggings and a tee underneath that you can dump at the airport of your destination. Then you can maybe reuse the maxi dress on the trip! A cardigan that you can wear or roll up and put in your carry on.
I vote for pants (not leggings) from Athleta or Lulu. They’ll be comfortable and have some stretch, many have a warm soft inner lining yet the outside is wrinkle free. Can dress up or down with a t shirt or something nicer. Just watch for zippers on pockets; they do set off security. Athleta even has a section “Commuter/Travel” and the Brooklyn ankle pants are super cute.
I also never wear dresses, skirts or shorts on planes, I get too cold.
You can always wear something like this:
https://www.dickssportinggoods.com/p/nike-womens-pro-5-shorts-18nikwpr5shrtxxxxapb/18nikwpr5shrtxxxxapb
I wouldn’t be able to wear full leggings under a dress. I’m sensitive to layers. ? I usually kind of tuck the dress so my thighs aren’t touching when I’m sitting. I totally get what you mean. In fact I might get those shorts I linked and try them out.
Scottevest to top off whatever else you are wearing!
I wear compression socks, too, on long flights. My feet and legs feel great when we reach our destination. I usually wear dark jeans with a light top and sweater. If you want to look dressier, try a scarf or pashmina.
Compression socks, hiking boots if I’m bringing them or Sketchers slip-ons, a big scarf that I’ll use for everything imaginable on the trip, comfortable knit pants, baggy shirt, knit shirt with no chance of cleavage showing, denim jacket. (I freeze on planes, and when I’m cold, I get unbearable muscle cramps. It’s pretty ugly.)