I agree with all of the comments that people are off in there own world and most won’t notice. For the last few years my travel attire has been Lululemon outfit of jacket shirt and leggings with Sorel ankle or knee boots. I will say I get noticed but nothing said and definitely not YouTube worthy. I have on 3 occasions wore 4” block heels, riding boots and stilettos but with jeans. No skirts on the plane, I’m always cold on the flight and don’t want to freeze my balls off lol. I did not carry another pair of shoes as at this point in time I could care less what others think. Again, at the end of the day 99.9 percent of people could care less especially theses days.
I have said in the past, “ I’m not here for a long time, I’m here for a good time!”
Adding, I have tsa precheck and sometimes the shoes come off and sometimes they don’t Not a big deal for me to take off my wedge Sorels or heeled shoes or boots, agents have never looked smirked commented. I’m sure they have seen it all and more. A guy in heels is no big deal to them.