Flying High In Heels or Flying In High Heels, That Is The Question..

I always gaze at other travelers who are packed so efficiently and lightly with such envy. They are usually crisply pressed and well dressed to boot, which makes it even worse. Then there’s the woman in high heels, the light makeup, the freshly coiffed hair and her smart little travel outfit, be it jeans, shorts or what have you, which usually just makes me stop and stare in silent awe and admiration. It reminds me a little of when my grandmother used to talk about how people used to get dressed up to travel. They wore hats and gloves and stockings and matching coats and dresses and shoes and bags. It's all so very MAD MEN.
Of course, no one dresses up that much anymore, but mind you, I’m still on the complete opposite end of the spectrum. I can usually be found wandering around the airport in sweats (that double as pajamas when I’m home, I'm sad to say). Sometimes they might be a snug fit (Juicy’s if they’re clean), but that’s usually about all the sexy I can muster on a flight that’s more than 2 hours long and those will usually be worn with Uggs (as in fucking ugly boots).
Needless to say I get a lot of suspect looks from airport security..
I have a friend that insists when I come to see him anywhere, I must not where those things on my feet! Of course he is gay but I’m pretty sure he’s only echoing the sentiment of most, if not all straight men.



On the other hand there is nothing worse that trying to be cute while you’re traveling and being totally miserable and worn the hell out when you arrive. I remember only too well traveling with my mom when I was kid and getting smacked upside the head for the smallest thing because her feet hurt. Still, whenever I see other people arriving at their destinations looking so fly, so fresh and so clean, clean, it makes me wonder why I always choose to run around looking like a damn homeless person. Especially when I am as PASSIONATE ABOUT FASHION as I am.. I mean, I’m running around with my head tied up in a rag up under a hat, so I’m not messing up my hair, no makeup (ok, every once in a while I will do lipstick), layers of sweats so I don’t get cold on the plane (it does get damn cold on the plane), uggs, and way too much damn luggage to boot!



Another point to consider though, is how people treat you when you’re dressed well as opposed to dressed like a bum. As I observe this strange breed of people I admire so much, I notice they are usually treated very well. They ask for something and behave in a way that suggests they expect their request to be granted. I, on the other hand, ask for something, am told no, then ask again only to be told no again, then insist, then demand, then start screaming for the damn manager. Only when the person attending to me is told that I too am traveling in business class, just like the well dressed person before me, do they concede and realize that my request wasn’t so ridiculous after all (hahahahahahaha). And that’s only some of the time, sometimes the person will be like “git yo’ raggedy ass on outta here, hell naw I aint updatin’ you’ mileage account, heffa you know you aint got no damn mileage account”, or “you know you don’t belong in the executive lounge, now git!”
Other passengers roll over my feet with their luggage, men DO NOT offer to help me put my bag in the overhead even though I am 5’2” and visibly struggling trying to get a bag more than half my size (yeah, I know, big for a carry on) higher than my head. They will however, offer to help the well dressed woman, even though she may be 5’11” and carrying a pocket book the size of a wallet. It’s ridiculous and of course it’s not something I’m unaware of, hell I’m in the music business. It’s just that I think I’ve kind of gotten in the mindset that where travel is concerned, it’s comfort first and worry about looking good when I get off the damn plane ergo heavy bags. But I’m thinking I need to rethink this whole travel effect.. So I’ve decided to try a little experiment, stay tuned..



The shoes I wore on the plane..