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The 1st time to meet(btw-we're married now), I wore a comfortable, but nice dress with black pantyhose(tights), but also wore elastic waist stretchy pants that flared over the mid-heel boots I was also wearing. (Reason for the pants was b/c it was very cold weather at both departure & destination.) I took the pants off before my final arrival.
Easy-wear pants are the simplest option for this- as well as either zip-up boots, slip-on shoes or Velcro, b/c you have to take your shoes off, belts if they're worn with pants for going through the security every time you have to change planes
(and during traveling, esp. while on the plane, it's much easier & quicker in the tiny on-board restrooms(toilets) than having to unzip, etc.).
I'll post what I do now when I travel in a 2nd post, which might have some options you'd like as well, but don't want it to be too confusing.
P.S.Winter scarf for neck is invaluable, too- when I was at the Amsterdam airport, everyone had them- from execs in suits to little kids- you still have to remove them and any coat or cardigan, jkt., etc. as well, when going through security, but well worth it(and onboard planes are cold, too)
Thank you! You are amazing, things I would not have thought of, if you travel often I guess it becomes second nature..I've never been out of SA before so your advice has truely helped! So glad it worked out for you too