Going to be -26C here tonight. On the plane tomorrow morning. YAY! HTH are you supposed to dress to travel with weather so different at each end?
There is no good way to answer this questions. I usually wear shorts, a t-shirt and a sweater and my wife usually wears Yoga pants, t-shirt and a sweater and we just suck it up in the cold here. We do the same on the way back.
We leave from toronto each year in february so not quite as cold as u will have it, but still below freezing. If u are leaving ur car at the airport I would leave a heavy winter coat in the car for urself when u get back. Wear the thinnest coat (or sweater) u can deal with from ur car to the airport and then tuck it in ur luggage before you check it. I personally would rock shorts door to door, but same can apply with pants. Wear some light pants to the airport and tuck them in ur luggage before you check it. Obviously the reverse goes when u get back. Keep ur lighter coat and pants easily accessible for when u get ur luggage back and u will have ur heavy coat waiting for u in the car.
For the man wear a pair shoes and pants that you could also go to one of the restaurants later in the week. Light jacket. Make sure you have a change of cloths that you can get into either on the plane before you land or as soon as you get to the resort. In case your room is not ready.
Put your winter coat in your checked bag when you enter the terminal when leaving. Take it out of your checked bag when you get your bag off the carousel when returning. I also take a change of clothes a swim suit flip flops and sunscreen in a back pack so if my room isn't ready I can change get some lunch and head to the pool.
The new lightweight puffy coats are great for travelling and take up no space in your carry on and super warm for some of our Canadian climate. I also do the yoga pant, tank and sweater thing to be comfy on the plane and ditch the sweater when we land. Can also be used for cooler nights when the wind can get up when in Cancun. As a rule wear your heavier clothes on the plane and choose something that can be worn while there. Layers are good too.
Shorts and flip flops both ways for me. I throw my hoodie or jacket in the car as I leave it with the valet at Skypark and put it on as soon as I get to the car. Valet is great for getting into a warm car when getting home. If we are parking at one of the STL hotels I start the car with my phone to speed up the warm up process. Getting out of the airport shuttle and stepping into 12" of snow is always a possibility although it has only happened once for us.
