Flying Pretty

One of my goals is to “fly pretty”,  a term that refers to going on a flight dressed.  I have no fear of doing it, but I have no travel plans on the horizon.  Flying pretty does take a lot of planning and really, there’s no going back once you get to the airport.

If you’re thinking about doing this, please watch this video by the TSA, and if you’ve ever flown pretty share your experiences in the comments.

Love, Hannah

16 thoughts on “Flying Pretty

  1. Hiya Hannah-

    Interesting new format. Well, I know it’s not new, but I am pretty sure this is my first comment here as opposed to your previous site. Looks good here!

    Anywho…. I have flown pretty. It was about a year or two ago and I had a series of flights across the country and back. I began in Fresno CA, went to Vegas, then to Chicago O’hare, then into Pennsylvania, and lastly from New York back to CA. Even though I was scared _____less, I went for it and am so happy that I did. I did not experience a single problem flying out of or into any of the locations I visited. It was very refreshing actually.

    I think that part of what needs to be kept in mind if one is wanting to do this, you need to have a bit of a sense of humor. I mean you’re going to have to deal with the situation of you handing your male ID and plane ticket over to TSA while you are dressed as a woman. More than once somebody said “well, bless your heart.” I may be from Cali, but I know what that is code for! Regardless, they still allowed for me to go through. Oh and there was the one TSA agent who ran up to the full body screener and said quite loudly, “that blond is a dude!” Again, what did I care? I was asked to step up and be scanned. They scanned me. A female agent (every time) asked if they could pat down certain areas on me. I agreed. They patted. They said I could go through. Wow! Not that big of a deal. But I suppose that if one is the touchy type that they may have gotten offended. My wife and I were flying together. I observed how they treated her and they did not treat either of us differently. I don’t have an issue with their procedures and I have a sense of humor.

    Having a perma-smile plastered on my face helped ease the tension with myself and every single person I encountered. It was a lovely trip and now I am pondering the idea of international travel while dressing pretty. Hmmm…. Who knows, it could happen! I never thought the first flights would ever occur, but I am so happy that I pushed myself to face those fears. Such a happy memory.

    Liked by 1 person

    1. Thank you so much for sharing your exciting story! How did people handle you not matching your male name on your boarding pass and ticket?

      Love, Hannah


      1. It was no different than it is in any other daily situation of using my male ID and credit cards while dressed as a woman. I was way more nervous about it, but they handled it the same way. They looked at my papers/ID and at me, and back and forth several times and then signed off and allowed me to go through the checkpoint.


    2. Hi i have flown several times en fenne, no negative comments although i know i dont pass as 100pecent female. I break the ice with who i sit next to.
      Please remember my next statement is about me and not about everyone else doing the same thing. I i introduce myself, hi i am __
      A little about myself, i am married two children , no i am not gay and no i dont want to be a woman.
      This usually puts theem at ease and we chat during the flight.
      One instance my seat was next to a young boy of 9. He did not look up from his screen for the first part of the flight. His mum was sat next to me on the other side. After a little while the young boy was telling me what he was doing on his screen.He also asked me questions which i was all to glad to answer, The big one are you a man , yes i am and i do like being a man.Why are you dressed as a girl, because i like womens clothing more than mens and it makes me happy. His mum winked and gave a nod of approval.
      I told him it doesnt stop me being a dad , a husband or a brother because of how i dress.
      His mum mouthed thank you to me.
      One thing i now will tell you the little boy was wearing multi coloured nail varnish on long nails.
      I had a great conversation with his mun and her son. The mum also told me he is usually quiet and not so chatty. and was nice i was able to be honest and open with him.
      Remember when you go out en femme be confident and kind, but also have the understanding that not everyone will be as comfortable in your company, you still have an amazing opertunity to show them you are after all a person.


  2. Hi Hannah and great post here. I fly in fem all the time now and used to all the thing that TSA does. They are very much trained on how to handle us and suposed to do it with respect. I have had inspectors look at my Id close and then at me and they sign the ticket and say have a nice day. Last week in Vegas the guy checking my Id said is this really you and then signed the ticket, kinda funnyThen on to the scanners. Every time I get pulled aside for my breast or hip forms and get the pat down and then move on. Never a problem. The TSA agent in the past post could have lost his job for saying that blond is a dude as that is not tolerable in there books. It is really fun flying in fem and now I have a hard time flying in male mode and quietly is boring. Only time traveling in fem is when getting on a cruise ship as they always want you to look like your ID or passport, so I grew out my hair so now they just make me pull it back and take my ships picture. Im going on a TSK cruise in a couple of weeks on a different cruise line so we will see how friendly they are during check in. Ok rambling now but definitive fly sometime and you will be hooked. Say Hi to Jenine W there as she got me on my feet years ago and I never looked back when she was here in colorado. RicciMarie


  3. I too have flown and cruised pretty. My situation is a bit different in that I mostly live fem to the point that my DL is fem but my passport being older is male. The name on both is the same so I have found it easiest to just have both documents together which makes it clear who I am no matter how I appear. I have never had a problem with TSA and they have always been courteous whether at a smaller or larger airport. The only issue I have had when cruising was my ship ID was taken when I boarded en-femme. During the cruise my son requested that we spend half the time with me “as dad”. Getting off the ship in port no problem. Getting back on was a bit more of a problem in that my shipboard id photo no longer matched my appearance. They just re-took my photo and following that experience I just finished the cruise in male mode. I have found that accepting myself and being confident in who I am is really all it takes. I would definitely recommend that if people want to have an experience going out en-femme to really consider flying and/or cruising. Again my experiences have been that these employees are some of the kindest and most professional people you will come into contact with. Beside when cruising they always have at least one elegant dress night and who among us doesn’t have that absolutely beautiful gown or dress we are dying to wear but which is way to fancy for a day out shopping.


  4. I did think of one other similar situation that may help other see encounters differently and that was with law enforcement. As I said my DL is femme. One time when driving home from an event with my son who had requested I go in male mode I was pulled over for a tail light that was out. I handed the officer my DL and he looked at it for a while. I asked if he had any questions about it. His answer was, “Nope the eyes match”. He handed it back, gave me the fix it ticket, and told me to have a nice night. So if you are traveling and the TSA agent, officer, or whomever seems to give your ID a bit more scrutiny remember that they are trained to recognize bone structure etc. and may just be confirming that the eyes in the photo really do match the ones you took so much time to make beautiful that morning.


  5. I fly pretty out of Pittsburgh, thru Dallas and on to Oklahoma city. I had no problem along the way even the rental car agent and the desk at my motel didn’t say a thing even though they knew my gender was not female. The same thing on the return trip, no problem. I talk to the flight attendant during one leg of my trip and I even ask her it I was her first. She said “first crossdresser”. She said she had no idea. I am so happy I did it. My next challenge is driving from Oklahoma to Pittsburgh dressed. I believe there will be lots of fun on the way. The toilet question always concerns me but be confident and be inn and out without lingering and drawing attention to yourself.


  6. I flew pretty last week coming back from Tampa Florida. While I was extremely nervous I should not have been. TSA was a breeze. I did have the luck to have been TSA pre that day and I think that is one of the reasons I decided to go. My first thought was that I was going to change in a family bathroom after going through TSA. Then I saw my pre status and got the gumption to go ahead. When I got to the gate the person did say my male name as I scanned my boarding pass. I was on Southwestern so it is find your own seat. I was in the A group and was lucky in that no one chose to sit next to me. No one ever challenged me but I think I was read more often that I usually am.

    So over all it was a great experience. I still remember walking down the airport looking at my heels. What a fond experience.

    Liked by 1 person

  7. This reply is on an almost three year old post; however, the information remains relevant. I was an in-home cross dresser up to the time when my wife passed away in late 2018. As part of my cleaning and clearing process I felt I needed to let my daughter know about me rather than discovering my cache if something happened to me. She was overwhelming in her support and encouraged me to keep pushing forward. We made a trip to the northeast so I could get makeup instructions that was more age appropriate yet still softened my features.

    I took those lessons and we spent the day touring the National Mall. We encountered at least four field trips. No one called me out. Later that day we flew out of Baltimore. Southwest took everything in stride as they accepted my checked bag. TSA did not even do a double check (so either I do not pass well or he was very well trained… I think the latter). I am in the pre-Check program so not full body scan. We sat in an airport bar for a couple hours. Maryland requires ID check for all alcohol purchases. Out wait staff referred to me as M’am the entire time. No one on our plane made notice of me either….

    I relate this story because I was once so afraid of leaving the front door. With a little education on makeup, deportation, dress, voice and never staring at anyone you pass by, you too can get out of the house and travel. While I have been out and about a few dozen times, the last for a manzilian wax, I am flying to Hawaii and staying enfemm most of the trip next week.

    Liked by 1 person

  8. So well put Hannah. I fly pretty in 2019 for the first time and documented it here. The biggest takeaway I experienced was people are just too busy at the airport to really care to really process or express a position. I had plenty of looks but luckily I was seated beside two women celebrating grandchildren.



Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s