The employer occasionally sends me out of town on business. This has always seemed to be a prime opportunity to spend hours dressed except for the possibility of getting caught going through airline security.
Last week was such an event but having read some of the experiences here, I decided WTF... Packing my bag the night before I threw in a skirt, blouse, half slip, bra, and panties for the entire trip. Oh and a makeup kit & cotton chemise with lace bodice. The only concession I made was to select a wire free bra. Seemed the rest of the stuff wouldn't show up on the X-ray but I didn't want any tell-tale double U's to show. Turns out I only have one... (must acquire more!) Thought I'd included a garter belt & stockings but apparently not and there wasn't room to bring the heels.
Outbound security screening was a breeze. No one raised an eye. Returning home was a bit more complicated as I was randomly selected for secondary screening (a pat down search). Again, no big deal. The pat down cost me a total of 15 seconds (then again I'm wearing shorts (underdressed with a VS hipster) and a T-shirt so there isn't a lot to pat down. Again, no big deal. But then TSA is just A Security Theater anyway.
Bottom line... Don't sweat the security! Traveling? Take her a long too! (at least it worked for me this week).