To Dress, Or To Overdress?

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.

To Dress, Or To Overdress?

Postby JeffB1959 » Fri Feb 23, 2018 9:42 am

Here’s a question worth pondering: is being overdressed a bad thing? When I embraced the unique lifestyle of the fashion freestyler, I made it a point to always, and I mean ALWAYS look my very best. I mean, if I was going to traipse out in public wearing women’s clothes AS A MAN, then I’d damn well better make sure I didn’t look foolish or inappropriate. Because of that particular mindset, I tend to think I overdo things, that I overdress. I want to look sharp, I want to look stylish, I want to look fashionable, but do I go overboard at times as a result? Perhaps.

Case in point: A few days ago on President’s Day, I went to the local casino to have a little fun and spend a little money, and while pretty much all the women there were in purely casual, even frumpy or sloppy clothes, there I was in a nice sweater, a pencil skirt, hosiery and heels, even for a place as innocuous as a slots parlor, I just couldn’t bring myself to dress down. Or on another occasion at the King of Prussia Mall, I sported my black leather jacket over a turtleneck, a dressy a-line knit midiskirt and high heeled knee boots, and I can assure you that NO other female, young or old was half as put together as I was, even though I didn’t need to be, but, I can’t help dressing up for outings like to the mall. I’ve said this a time or two or a dozen, and I believe it to the max: when I look good, I feel good, since wearing women’s clothes is great fun, I want to do it right. Perhaps vanity plays a part in my habit of overdressing because I like to show off, to display my fashion style since I look better in women’s clothes than I do men’s, something that’s also fun as I just love strutting about in a skirt and heels, it’s a highly intoxicating feeling.

To everyone reading this piece, regardless of your level of commitment to freestyling, if you wear just one article of clothing or go the whole hog like I do, it’s important that you take pride in your appearance when out in public. That you put a premium in being knowledgable about fashion and looking your very best, because you’re setting an example to the whole world for men who wear women’s clothing, and that example should be we CAN look tasteful and stylish in the clothes we choose to wear and not odd, freakish or embarrassing. I don’t mind admitting I obsess over looking my best, I never go out unless I am, so, if that results in being occasionally overdressed for the surroundings I happen to be in, I don’t mind that at all. If anything, I’m rather proud to say I overdress, like everything when it comes to freestyling, it’s a thrill. Opinions?
I don't want to LOOK like a woman, I just want to DRESS like a woman.
User avatar
Member Extraordinaire
Posts: 1135
Joined: Mon Aug 20, 2007 3:19 pm
Location: Pennsylvania

Re: To Dress, Or To Overdress?

Postby crfriend » Fri Feb 23, 2018 10:06 am

From a my own perspective, given the generally slovenly appearance that's so common nowadays, I'm happier being slightly overdressed than not. So, yes, I try to do my level best.
Retrocomputing -- It's not just a job, it's an adventure!
User avatar
Master Barista
Posts: 10474
Joined: Fri Nov 19, 2004 9:52 pm
Location: New England (U.S.)

Re: To Dress, Or To Overdress?

Postby oldsalt1 » Fri Feb 23, 2018 11:11 am

While I would never really go out sloppy. It was at times casual just a fast glance at the mirror to make sure I didn't look like a clown.

Now with skirts and dresses it has to be right. I have to admit I have fun doing it but It has to match, coordinate and be one step above .

When ever I had something major I did come to the café where I had my intended outfits critiqued by the members . There was at time some harsh comments and a hell of a lot of great suggestions.

I gained a great deal of fashion sense from the suggestions of the members

I truly agree with Jeff that you have to dress better that those around you.
User avatar
Member Extraordinaire
Posts: 2014
Joined: Sat Jul 09, 2016 8:25 pm
Location: Long Island, New York

Re: To Dress, Or To Overdress?

Postby Jim » Fri Feb 23, 2018 12:00 pm

I don't dress to impress, but rather go for casual comfort. I've progressed from cut-off shorts to hemmed shorts to skirts when I feel OK about it, and am trying more not to be too sloppy, but I have mostly a utilitarian approach and try to avoid vanity. I learn from you other guys with different ideas, but I will continue to be myself.
User avatar
Member Extraordinaire
Posts: 625
Joined: Mon Aug 27, 2012 1:39 am

Re: To Dress, Or To Overdress?

Postby Fred in Skirts » Fri Feb 23, 2018 6:28 pm

I dress for comfort!! I do try not to look sloppy and do try to match my colors BUT and it is a big one I have to be comfortable at all times. Not just with my self but with all of the clothes I wear. When I decided to go skirts 100% I knew it would be hard to do because I am not all that fashion aware. I used to wear blue jean shorts all of the time and they do not look like fine clothes. Now I dress a lot better because skirts even denim ones look nicer than the shorts. I mix and match with some mens shirts or womens tops, what ever feels good that day.

Fred :kiltdance:

:whistle: Hi I am Fred and I wear skirts and dresses all of the time. :hooray:
"It is better to be hated for what you are than be loved for what you are not"
Andre Gide: 1869 - 1951
User avatar
Fred in Skirts
Member Extraordinaire
Posts: 2357
Joined: Mon Mar 14, 2016 6:48 pm
Location: Southeast Corner of Aiken County, SC USA

Re: To Dress, Or To Overdress?

Postby Ralph » Fri Feb 23, 2018 6:38 pm

I guess it depends on how much attention you want to draw to yourself, and not necessarily in a good way.

Forget about the fact that to much of society what you choose to wear is "inappropriate" for your sex. Just look at it from the point of view of cultural expectations for a given environment. Would you wear a tuxedo or even a 3-piece suit to Walmart (Asda in the UK) or to McDonald's? To pump gas, work out at the gym, rake leaves?

There are times I want to stand out, show the world I don't care what society thinks, fly my freak flag... and there are times I just want to go out, get stuff done with minimal hassle or confrontation, and get home again. On those occasions, I dress to blend in.

So there's no right or wrong answer to your question, only your own standards for how much you wish to express yourself at any cost vs. how much you want to look like, and be treated like, just an anonymous face in the crowd.
Member Extraordinaire
Posts: 306
Joined: Wed Jun 26, 2013 9:07 pm

Re: To Dress, Or To Overdress?

Postby beachlion » Fri Feb 23, 2018 8:01 pm

I have no sense of fashion or aesthetics in the field of clothing. I never followed fashion trends actively but I had to buy what was in fashion because that was the stuff you would find in shops.
But I can appreciate a well dressed person considering the place, time and occasion of the moment.

I dress for comfort. When I'm dressed for the occasion, I feel comfortable even if the clothes are not that comfortable. When I first went out to an opera, I bought a smoking (more or less a tuxedo in the USA) and I was one of a few smoking wearers. And I felt good about it. After that there were a few other occasions like a reception at the Brazilian ambassy in The Hague as part of the Carnaval celebration. I have no idea if I will ever wear that smoking in the USA.

Now I dress casual if I can but I will go more formal if needed. My colors are blue, black, white and red. The last one as an accent. I think you can mix those colors without any problem with the fashion squad. My shorts became my skirts and that is the way I do my skirting. Now and then I try something different like tights or heels but I still don't go out with these because I don't feel that it is a part of me. Maybe it needs some time to mature.
All progress takes place outside the comfort zone - M J Bobak
User avatar
Member Extraordinaire
Posts: 1189
Joined: Wed Aug 14, 2013 3:15 am
Location: Allentown, PA, USA

Re: To Dress, Or To Overdress?

Postby phathack » Fri Feb 23, 2018 10:59 pm

I like to think of it as being properly dressed not overdressed, its how I prefer to dress.
The fact that others choose to dress like a homeless bum is a reflection on their self worth.
Just another example of how society and social discord continues to deteriorate.

User avatar
Member Extraordinaire
Posts: 249
Joined: Wed Nov 24, 2010 6:41 pm
Location: North Texas, USA

Re: To Dress, Or To Overdress?

Postby skirtingtheissue » Sat Feb 24, 2018 12:41 am

I never liked fancy dress in standard male clothes -- still don't enjoy wearing coat and tie which I do maybe 2-3 times a year. I never gave much thought to what I wore every day, since it was the usual boring male clothes; I dressed for practicality, from shorts and T shirt to blue jeans, polo shirt and sweater, etc. And I didn't pay much attention as to what shirt went with what pants.

But wearing skirts HAS made me much more aware of being sensibly dressed as I try to make the top go well with the skirt. But as to the level of dress -- the question of being " sharp, stylish, and fashionable" -- I don't go too far there. I like to avoid the grubby or plain look (hardly ever wear a T-shirt, for example), but like to wear a nice blouse and skirt that make a good look combined. I also don't make a complete top-to-toe freestyle look as I don't do hosiery or women's shoes.

So I definitely don't "overdress" in the sense of being too formal. Any overdressing of mine would be in the sense of being a little more feminine than I should be or than people expect, and I don't mind doing that. I love flowy and/or floral or otherwise pretty skirts and tops. So, Jeff, I agree with you when you say "like everything when it comes to freestyling, it’s a thrill", but I don't care to be overly formal.

When I heard about skirting, I jumped in with both feet!
Member Extraordinaire
Posts: 334
Joined: Sat Jul 21, 2012 1:25 pm
Location: southern New Hampshire

Re: To Dress, Or To Overdress?

Postby Grok » Sat Feb 24, 2018 1:11 am

Some members, such as Jeff, have a particular flair for clothes. (A flair I lack). They shouldn't worry about overdressing-they are displaying a talent, and the world is a better place because of it. :D
Member Extraordinaire
Posts: 1805
Joined: Fri Aug 29, 2008 2:21 am

Re: To Dress, Or To Overdress?

Postby denimini » Sat Feb 24, 2018 2:11 am

When I go out to dinner or some similar engagement I do like to look smart but with me there is certainly no danger of being overdressed. I do care how I look and even when I am doing dirty work I like to portray a practical look. If I am happy with what I see in the mirror(s), I can go out with complete confidence regardless of what other people wear or think.
I also think each individual is capable of portraying a different style, taller persons seem to be able to carry a higher level of dress in the same situation. I am not tall (despite my mother's assurances when I was growing up).
I am not sure what "overdressed " would be; I could understand the concept of inappropriate clothing, such as wearing a floorsweeper and high heels on a bush walk. Overdressed might be like saying "over fit", "over intellegent" or "over organised", to appease the discomfort of the less endowed.
Anthony, a denim miniskirt wearer in Outback Australia
User avatar
Member Extraordinaire
Posts: 1469
Joined: Wed Jan 07, 2015 2:50 am
Location: Outback Australia

Re: To Dress, Or To Overdress?

Postby Caultron » Sat Feb 24, 2018 3:50 am

Most women these days seem to think a skirt and heels is overdressed for anything, so I suppose in that sense, I do overdress.

And I do try to put together a coordinated outfit, which again may be overdressed compared to others.

But once you've decided to wear a skirt in public, you may as wear what you like with it. Take hints from men's fashion, take hints from women's fashion, and then enjoy.

(But I'd still think twice before wearing an evening gown or a Wonder Woman outfit.)
Courage, conviction, nerve, verve, dash, panache, guts, nuts, balls, gall, élan, stones, whatever. Get some and get skirted.

User avatar
Member Extraordinaire
Posts: 4122
Joined: Tue Jan 15, 2013 4:12 am
Location: Phoenix, AZ

Re: To Dress, Or To Overdress?

Postby Sinned » Sat Feb 24, 2018 11:27 am

I wore suit, tie for most of my working life in an office and as a Manager so am used to dressing up. I went through the sixties so casual became my style outside of work. To a certain extent it still is but I do have to learn to dress up with a skirt. I have few skirts that I could consider dress up items, mainly velour, because I never considered dressing up when I started. I have realised that dressing up now with traditional women's clothes is a completely different scenario and one I am going to have to think about. My aim with casual is to be in the situation I was in with trousers - throw some things on, know that they would match and not to think about it too much.
I believe in offering every assistance short of actual help but then mainly just want to be left to be myself in all my difference and uniqueness.
User avatar
Member Extraordinaire
Posts: 3736
Joined: Sun Aug 19, 2012 5:28 pm
Location: York, England

Re: To Dress, Or To Overdress?

Postby STEVIE » Sat Feb 24, 2018 7:56 pm

I will dress to suit circumstances and myself.
Trousers when a skirted male would be inappropriate or wrong in my own opinion.
On skirted occasions, I will always take care over being "believable".
Colour and mixed styles to blend and not conflict.
I truly believe that this is my best attempt toward true acceptance.
In my little corner, it seems to be working.
I have become a common "sight", that is largely not seen.
My case rests!
Member Extraordinaire
Posts: 1890
Joined: Fri Sep 17, 2010 11:01 pm
Location: North East Scotland.

Re: To Dress, Or To Overdress?

Postby JeffB1959 » Sun Feb 25, 2018 10:53 am

Thanks for the compliments, everyone! I appreciate them greatly.

We all have our own description or viewpoint of what it means to "overdress", and that's a good thing because it means we all have our own ideas about what it means to be fashionable. At the end of the day, we all have to be true to our true selves and to no one else. In the beginning, I didn't much care about being fashionable, today, I practically obsess over fashion because I want to look nothing less than my very best when I'm out in public. That means a great deal to me.

Speaking of which, when it comes to fashion, we, as men, are far behind the learning curve. When it comes to how to wear women's clothes and how to put together stylish and tasteful outfits, we're learning in our 30's, 40's, even 50's what women learned as little girls, so we have do a lot of cramming in order to catch up with them, if that's your ultimate goal. Not to brag, but I like to think I've done well for myself, in fact, I've been complimented by women on my outfits, shoes, jewelry, even my handbags, so I guess I'm doing something right. But, that doesn't mean I sit on my laurels, no sir, I continue studying, continue learning all I can about fashion so I continue looking my very best.

Oh, by the way, Caultron, for whatever it's worth, I've never ruled out the notion of wearing an evening gown. I'd just need to find the right gown and the right situation to wear one. :lol:
I don't want to LOOK like a woman, I just want to DRESS like a woman.
User avatar
Member Extraordinaire
Posts: 1135
Joined: Mon Aug 20, 2007 3:19 pm
Location: Pennsylvania


Return to Freestyle Fashions

Who is online

Users browsing this forum: No registered users and 1 guest