going out in Chicago?

[Cynthia T]

I do not go out --period. My tastes run to skirted suits and heels. I had thought of going out on a dark, deserted street or suchlike, but that kind of outfit would stand out.
Then I thought of boldly walking through the Loop in the evening, shortly after rush hour. Many women downtown wear business dress, so one more, albiet not as good looking, wouldn't be unusual.
Any thoughts?

[rita63]

I have never gone out either but I am going to Toronto in a few weeks and planning to go out in the evening as dressed as I can, jeans blouse bra stockings makeup, hair dow nand styled, nails painted. My hotel is near the gay village so I should fit in.
Give it a try Cynthia it should be a gas.

hugs rita

[Rogina B]

Just do it! Then tell us all how it went...lol Have fun,life is way too short.

[Melissa Rose]

Repeat after me...."Thou shall not walk down a dark, deserted street alone". Maybe in a very safe residential area, but it is still not a good idea. Don't let your desire to go out make you throw away common sense and intelligence.

Whether you stand out or blend in will depend on a lot more than just what you are wearing. Your size, walk, body language, etc. also makes a big difference. Differences are more apparent when direct comparisons can be made. If there are a lot of GGs around, the contrast between yourself and them may be more obvious. You may be the tallest or biggest woman among the crowd so you may stand out even more. If you try to hide or be inconspicuous, you will stand out. Your attitude influences how much you stand out. Act like you have every right to be there, act like there is nothing unusual going on and be comfortable (even though there are a million butterflies in your stomach). Most people are too wrapped up in their own thoughts to notice everything that is going on around them. Just don't give them an obvious reason to notice you. If it happens, are you mentally prepared to be read and perhaps pointed out in such a crowded and public location? While it is unlikely someone will say something or make a scene, have a sense on how you will handle it. A smile goes a long way to disarm a potentially embarrassing situation.

Back in October, I spent 5 days in downtown Chicago and never went guy at any time. I flew into Midway, took a taxi into downtown, checked into the hotel, came and went for 5 days, and returned to the airport by taxi without any problems or issues. I never encountered a problem at stores, malls, restaurants, bars, the Lincoln Park Zoo, museums, in taxis and any other place. So be safe and sane, and you should be fine.

[Ressie]

Walking and body language would be my biggest challenges. I think with the right make up and wig I could be close to passable, but my mannerisms, walk and talk... nope. :) I would have to get heels with extra support or go with flats. And my hands!... too big!

[Barbara Ella]

Please dont go out at night in Chicago... Stick to the loop after rush hour. Work on your mannerisms, walking is the big one.

Have fun, Barbara

[WyrmQueen]

I suggest you go out in Boystown. It's the LGBT neighborhood so you'd be relatively safe.

[Noel Chimes]

"Thou shall not walk down a dark, deserted street alone".These are words to live by. Wanting to go out is a natural progression but common sense is needed here. Go and check out the Loop or Mellenium Park or Navy Pier and see what everyone else is wearing, and how they carry themselves. Make some mental notes about what is going on. Just relax and enjoy.

[RADER]

As stated above; do not go out at night.
The best time is High Noon; Like you said, there are plenty of office type down town,
And one more on a shopping lunch break would raise no interest.
I would be cautious of after rush hour, that is when the stragglers of after work get
bothered the most. Nobody see anything as they just want to get home.
Be carefully of boys town area; North Clark or Lincoln near Diversey, Someone burned
down a Gay night club in Oak brook, and they where concerned about the club they have
in boys town.
Rader

[Beverley Sims]

You are living on the edge if you do any of what you are thinking, and in Chicago.
I felt the vibes there in the daytime and downtown only.
No dark streets, no night loop, no nite time.
That is the way I felt, yet in New York it seemed a lot safer but still no nite time.
Nite time in Las Vegas.... Now that's a different story.:)

[SANDRA MICHELLE]

I also suggest "boys town", just google search the locals. Chicago has many locations that are friendly to gays and CD's., just be careful. I unfortunately can not frequent the Cd friendly locals in my home town because my daughter lives there and has many friends in the area that are gay and they all know me only as my dad side.

[Phoebe]

Might check out the Chicago Gender Society page, there are links to Chicago night life: http://www.chicagogender.com/Resources.htm Also there some events at Hunters in Elk Grove, Temptations in Franklin Park, The Hideaway in Oak Park, Forest View Lounge on South Harlem.

[Cynthia T]

Thank you all for the informative replies!
Beverly: I'm sorry you didn't like the Chicago 'vibe'. I live here, so I'm comfortable.
Melissa, Noel, et. al: My definition of "Dark and deserted" was a residential street in the evening--no dark alleys, fur surre!
Sandra, Queen: I know Boys Town. Very young (I'm not) very casual (see previous). Older woman in suit and heels would really stick out. I was thinking the Loop when there were still people about, just not so many as lunchtime, and I would be dressed like the other GG's.
Janet: I know of Tri-Ess, gender society, Hunters, etc, but I do not think I want the sort of interaction, even with other gurls, that going to a club would require.
Maybe I'll try this some day.
Cynthia

[suchacutie]

My suggestion would be the loop on a lovely day at lunchtime!. I think that fits all your categories and is wonderfully safer.

If you choose boyztown I would suggest the 7-9 timeslot so it's still light but there are enough people to "get lost" in, as long as it's with jeans and a top!

Please do let us know how it unfolds!

tina

[StaceyJane]

As others have said the safest is during the day in a public place. Personally I feel no need to go to any gay oriented places. I don't think they are any safer.

[WyrmQueen]

OK, a lot of misinformation here.

First of all, you can very much go out at night in certain neighborhoods.

Second, saying he can only go out at downtown is false. Boystown and Andersonville are two very prominent LGBT neighborhoods in the city. She can very well go out in while crossdressed in those two neighborhoods, even at night.