Going out for the first time. Outfit suggestions?
Posted: Tue Jul 09, 2019 7:46 pm
I’ve decided I’m going to swallow my fear and step outside for the first time in a skirt. I’ve always been so paranoid and telling myself that skirts are not for men, and everyone’s eyes are gonna be on my skirt and I’ll be a laughingstock. But the truth is, even if I am, I don’t know these people. The chances of meeting someone I know personally are extremely low, and the chances of meeting anyone who remembers this (and laughed at me) again are even lower.
I have some errands to run in New York City next week, and it’s going to be hot. If I know anything about New Yorkers: they don’t give a flying F about anything. Even I’ve seen men walking down the block in skirts and dresses before. Some of them M to F transsexuals (pre-op, noticeable), others were just average dudes like me, only in a skirt instead of pants. People on the streets of Manhattan are only concerned about one thing: where they need to go. They don’t have time to stop and take another look at something out of the ordinary, and a good majority of them just don’t care.
So with all that in mind, I’m going to take my first step, literally, into wearing skirts in public. I’m going to feel awkward, I’m going to feel anxious, I’m going to think it’s a bad idea the entire time. But once it’s out of the way, I’ll be proud of myself for doing it. The most I’ll feel exposed and anxious is on the train, in the train station, and walking to the places I need to go. Hopefully my Uber driver can drop me off directly in front of the door so I can run inside.
I’ve decided on a black and white, plaid, pleated mini skirt. I’m about 5’9”, so the hemline is just about an inch and a half above my knee. I’ve chosen this one because it’s not too flared, it kind of just flows down from the waist, and it’s pleated in a way that gives it the illusion of being a pair of really baggy shorts. I figured this would be a good start to just get it over with, and hopefully gain some confidence to do it again. Like Frank Sinatra said: “If you can make it here, you can make it anywhere.”
If anyone has ever been to New York, you know that it gets scorching hot in the summer. I’m looking to be comfortable, but I’m not looking to bring attention to myself (any more so than a man in a skirt would bring to himself). What should accompany my skirt on my day out in NYC? I normally wear a baseball hat, and I’ll probably wear my sunglasses indoors if I have to calm my nerves. Should I ditch those too? What types of shoes? Any suggestions will be greatly appreciated, and I’ll be sure to let you all know how it went, and maybe even post a before and after picture. Thank you so much!
I have some errands to run in New York City next week, and it’s going to be hot. If I know anything about New Yorkers: they don’t give a flying F about anything. Even I’ve seen men walking down the block in skirts and dresses before. Some of them M to F transsexuals (pre-op, noticeable), others were just average dudes like me, only in a skirt instead of pants. People on the streets of Manhattan are only concerned about one thing: where they need to go. They don’t have time to stop and take another look at something out of the ordinary, and a good majority of them just don’t care.
So with all that in mind, I’m going to take my first step, literally, into wearing skirts in public. I’m going to feel awkward, I’m going to feel anxious, I’m going to think it’s a bad idea the entire time. But once it’s out of the way, I’ll be proud of myself for doing it. The most I’ll feel exposed and anxious is on the train, in the train station, and walking to the places I need to go. Hopefully my Uber driver can drop me off directly in front of the door so I can run inside.
I’ve decided on a black and white, plaid, pleated mini skirt. I’m about 5’9”, so the hemline is just about an inch and a half above my knee. I’ve chosen this one because it’s not too flared, it kind of just flows down from the waist, and it’s pleated in a way that gives it the illusion of being a pair of really baggy shorts. I figured this would be a good start to just get it over with, and hopefully gain some confidence to do it again. Like Frank Sinatra said: “If you can make it here, you can make it anywhere.”
If anyone has ever been to New York, you know that it gets scorching hot in the summer. I’m looking to be comfortable, but I’m not looking to bring attention to myself (any more so than a man in a skirt would bring to himself). What should accompany my skirt on my day out in NYC? I normally wear a baseball hat, and I’ll probably wear my sunglasses indoors if I have to calm my nerves. Should I ditch those too? What types of shoes? Any suggestions will be greatly appreciated, and I’ll be sure to let you all know how it went, and maybe even post a before and after picture. Thank you so much!