Going out for the first time. Outfit suggestions?

Discussion of fashion elements and looks that are traditionally considered somewhat "femme" but are presented in a masculine context. This is NOT about transvestism or crossdressing.
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trdrl92
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Going out for the first time. Outfit suggestions?

Post by trdrl92 » 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!

trainspotter48
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Re: Going out for the first time. Outfit suggestions?

Post by trainspotter48 » Tue Jul 09, 2019 8:40 pm

My suggestion is for the rest of your wardrobe to be what you'd be wearing without the skirt. Male polo or T shirt, short socks - not pulled up to the knee, trainers (sneakers) or sandals - if you go with the sandals you can even ditch the socks, ball cap or similar.
And just be careful how you sit down!!

Best of luck.

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Re: Going out for the first time. Outfit suggestions?

Post by skirtyscot » Tue Jul 09, 2019 9:36 pm

I agree with trainspotter48. Wear whatever you would wear with shorts.

It's quite a bold choice of skirt, IMO. If you want to blend in as much as possible, denim would be the thing to go for. The length seems fine from your description.

Go for it! You may find it nerve-wracking at first, but that will pass.
Keep on skirting,

Alastair

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oldsalt1
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Re: Going out for the first time. Outfit suggestions?

Post by oldsalt1 » Wed Jul 10, 2019 2:38 am

Wear a denim skirt a matching tee shirt low socks and sneakers
It is a very big step to take a trip into the city. But I have to tell you there is so much going on and so much diversity that nobody cares.

And if any body does look they are probably from out of town and just consider you as part of what NYC is

I am much more at ease walking around NYC than I am around my home town.
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oldsalt1
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Re: Going out for the first time. Outfit suggestions?

Post by oldsalt1 » Wed Jul 10, 2019 2:56 am

I was the most uneasy when I was at the LIRR station waiting to get on the train. I felt that with only a few people around I stood out. For on the train bring a paper with you this way you can cover your lap NOBODY CARES once you get into the city NOBODY CARES as long as you are dressed conservative NOBODY CARES

Relax and enjoy the trip.

In my opinion I would not wear a 2 tone skirt. it will draw more attention even if a woman wore it I know my blue outfit is a little boring but it blends in better.

Think of it this way what would you be least likely to notice if it was worn by a woman.

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oldsalt1
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Re: Going out for the first time. Outfit suggestions?

Post by oldsalt1 » Wed Jul 10, 2019 9:48 am

One more point whatever skirt you choose it should have pockets. If you don't you will need to carry a bag . and the first time you don't need the additional problem of remembering the bag.

Kohls has a good assortment of denim skirts. croft and barrow had a decent set of pockets . once in the city I would carry my phone and wallet in front pockets.

Limit keys to just what you need car and house .

The best way to enjoy the trip is to limit distractions Take just what you need. NOBODY CARES have a good trip

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oldsalt1
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Re: Going out for the first time. Outfit suggestions?

Post by oldsalt1 » Wed Jul 10, 2019 3:25 pm

Sorry for so many post but as I think of things.

The train ride from Hicksville to Penn is just a 30 minute hop. But I think that the most likely possibility of running into a neighbor is at the station.

If you want to avoid this possibility I would run down to Sunrise highway and take a train on the Babylon branch. Also if you have a chance buy your ticket in advance less contact while skirted.

This is a very big step take a deep breath and work your way thru it.

BTW had to see a client in Oceanside this morning on the way home I stopped at Ariola's for some pastry than ran up to BJ"S for gas NO problems nothing oh I forgot the lady in Ariola's said I looked nice.

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Re: Going out for the first time. Outfit suggestions?

Post by K_Highlander » Wed Jul 10, 2019 4:17 pm

Kohl’s has a good selection of skorts too.
Very easy to convert to skirts by carefully cutting out the shorts.
K

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Re: Going out for the first time. Outfit suggestions?

Post by beachlion » Wed Jul 10, 2019 4:19 pm

I went to New York to appliy for a new passport at the Dutch consulate.
viewtopic.php?f=67&t=20405

I did not go quite plain clothed. No problem at all beside of some snickering behind me when I bought the tickets.

You have to build up confidence and you only can do that wearing a skirt in public. Like the others said: baby steps. After some time you wonder why you were so afraid. And you are lucky with your wife supporting you. That is the first battle won.
All progress takes place outside the comfort zone - M J Bobak

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Re: Going out for the first time. Outfit suggestions?

Post by Happy-N-Skirts » Thu Jul 11, 2019 1:04 am

Another thought is to go walking on a nature trail, regional park, national or state park, nature preserve, or wilderness trails. We live near the Pacific Crest Trail and it crosses roads in several places. Look at a map of the trail and plan a hike either by yourself or someone else. My wife and I have done a fair amount of trail hikes while skirted. I go alone about once a week in different places. Yesterday I was in a part of the national forest and stopped for lunch, gas, cup of coffee, and three stores going and coming home.

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Re: Going out for the first time. Outfit suggestions?

Post by Skaterswaltz » Fri Jul 12, 2019 11:48 am

This sounds like tremendous fun, so embrace it. Certainly take a deep breath before you step out, as concerns can’t go away until you step out. I think your choices are good, and do take on board other advice here. The farther you get from home, the better it is because then, when you just have to be out there, you deal with it.
And the thrill when you get home is a rush. Reflect well.
I’ll be out today. The one I’ll be in is like my shorts, but it’s a choice for being cotton with pockets. I have flair ones that are obviously skirts and not shorts. It’s hot out there, and we don’t have to be hot under there, guys.
Think best case scenario, enjoy being out and about, enjoy your day, and have a nice cup of tea when you get back, and tell a waiting ‘us lot’ how it went. You’re not alone.

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Re: Going out for the first time. Outfit suggestions?

Post by GerdG » Thu Jul 25, 2019 5:08 am

trdrl92,
it is about one week ago that you were to wear a skirt first-time out. On Manhattan. And you had all the good reasons for doing it and not being afraid. Did you manage, or did you after all chicken out? And if you made it, how was it?
GerdG

There ARE viable alternatives to trousers.

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