Wearing Leather and Boots on Airplanes

I was at a conference earlier this week, and traveled home as planned on October 31. Yeah, that also happens to be Halloween.

Earlier in the day, I appeared in my dress leather jeans, pink shirt, and black Lucchese goatskin dress cowboy boots when I gave a presentation before a large plenary meeting. I explained that I am a “breast cancer aware biker” and (most) members of the audience laughed politely.

I had to return the pink shirt to a friend from whom I borrowed it, so while I was changing, I thought perhaps I should change into a pair of regular denim jeans and boots that are easier to take off when going through security before I headed out for the airport right after the conference ended. But then… I had second thoughts.

When I took off the pink polo shirt, I put on a blue regular cotton dress shirt. I like to fly in that kind of shirt for the convenience of the pocket. Then I sat down and took off my Lucchese boots, which took a bit of pulling since those boots fit more snugly than some others that I own.

I decided, however, not to change my pants. Those leather jeans looked good, and it was Halloween, after all. I thought, worse-comes-to-worse, if someone says something about the leather, I can always turn to them and say, “Happy Halloween!”

I pulled on a pair of black roper cowboy boots (which are far easier to remove when going through airport security), tucked in my shirt, closed my belt, then looked in the mirror and smiled. Nice!

Travel to the departure airport was by shared van service. No one — not the driver or the other passengers — said a thing about the leather jeans. I got to the airport and waited out front for a little while to meet a friend to say goodbye. I noticed other people looking at the leather jeans, but no one said anything.

After having a conversation with my friend, I checked in for my flight and went off to security. Again, the first screening agent only looked at my boarding pass and identification, and waved me through.

When I got to the magnetometer, I took off my belt and boots, and put them in a plastic tray. I pulled my laptop out of its case and did the same. I pushed them through the machine and stepped through the x-ray. The TSA agent on the other side had been appearing to be generally bored, but when he saw me, his eyes lit up. He stood straighter and smiled.

With some degree of enthusiasm, he asked me about the jeans, how comfortable they were, if they were hot, and whether I ever wore them tucked into boots. This guy was genuinely interested in the leather jeans! (I think — seriously — he was only interested in the jeans and not me. That’s just fine.)

However, the security lines were long and busy, so he couldn’t take but a few seconds — seemed like longer — to ask questions and receive simple answers before he had to pay attention to the next passenger. I smiled at him while I sat on a bench so I could put my boots back on. He waved in response, then again, redirected his attention to his work.

I casually strolled to a food court, and stood in the middle whilst trying to figure out what I wanted to eat for lunch. While I was staring at the menu, I heard a child say, “look at those shiny pants, Mommy!” The Mom looked at me and asked, “do you play in a rock band?” I replied, “no, I don’t. I just like how comfortable and good-looking these pants are.” She said, “okay, cool” then turned to her son and said, “he likes them too, Billy.” Who knows, some day her son may want a pair of leather jeans (LOL!)

Nothing else much happened. Several flight attendants on both of my flights (first leg and connecting flight) complimented the leather pants. One flight attendant gave me an extra piece of candy that they were distributing to passengers for flying on Halloween, saying, “nice pants.” Yes, I did notice other people looking at me as I was walking from one gate to another at the connecting airport, but no one said anything.

So that was it — a big “non-event.” It is possible, and easy, to wear leather jeans and boots while flying, and few people will say anything. Those who do have something to say either have questions or are complimentary.

I have done that before — went to airports, through security, and flew while wearing leather jeans and boots. No one — ever — has said anything other than occasional compliments. If you are afraid to wear leather in public, it is your own fears holding you back. Relax, stand tall, walk proudly, and smile.

Life is short: wear leather!

8 thoughts on “Wearing Leather and Boots on Airplanes

  1. I miss weaing my boots when I have to fly. The tight connections have been the downfall for me. No matter how comfortable the boots, sprinting through the airport trying to catch my next flight before it takes off is no fun!


  2. Similar experience today. Today is “school colors day” here in Jr. High. I have on my new-to-me 19″ Paul Bonds with light tan vamps and NEON-green shafts. I wear boots to work (I’m a teacher) sometimes and no-one says much any more. Every once in while, but not often. But, I’ve never worn anything this loud to school before. One of the teachers (fellow boot wearer) noticed the ostrich skins, but that’s about it. Realize that I live in a northern state where few guys wear boots.

  3. BHD, I think the leather jeans look good on you, in part, because of your undoubted self-confidence and the evident enjoyment you get in wearing them.

    I sometimes see guys wearing them on Manhattan streets and if they are self-confident, they evince a more stylish persona. But other guys seem to be unsure of themselves and even though they are wearing the jeans, they still don’t ‘pull it off’. All of which is to say that some portion of looking good in anything is psychological. Your last two sentences tell the tale completely, “…If you are afraid to wear leather in public, it is your own fears holding you back. Relax, stand tall, walk proudly, and smile.”

    So in addition to finding a nice pair of leather jeans – and boots – to wear, one should also savor the experience, the comfort, the pride in wearing them and step out confidently knowing that in doing so, you’re letting the whole world know, to borrow a phrase a former U.S. President, you ‘have the brass’ to do so while others do not.

  4. I have started to wear my tall boots when flying as well. I like having them on trips and they take up so much room in the suitcase, so it really is the most efficient way to travel with big boots. I usually wear a pair of 20 inch Wesco engineers or harness. And I have to say, every time I pull them off for security at least one guy approaches me and compliments my boots. They usually want to know where to buy a pair.

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