"It depends" and why it is so hard to be a cross dresser

[Jenniferathome]

I am amongst the group of cross dressers who is open about this to his wife. So, I invariably ask my wife if some top goes with a skirt or what shoes work with what dress, jewelry whatever., and while I get the occasional "Yeah, that works," more often than not, I seem to get "It depends," as an answer.

The subtlety of women's fashion is astounding. Wear a necklace over or under the collar? It depends. Skirt too short? It depends. Is it no wonder that we struggle with fashion?

[Allsteamedup]

I tell my cder that there is a different bra for each outfit. When it comes to how well things fit or hang we are precise in the underpinnings as well as accessories. Few GGs would put a necklace over a collar these days; it would hang next to the skin in a notched or scoop neckline. Most tops look better inside a skirt if it has a defined waistband. If you want to wear a belt make sure it comes on the body to flatter not cut you in half. TYhat's why 'it depends...'

[CD_DIANE]

"It depends" on who you are trying to please OR if you are trying to pass OR if you are making a fashion statement . Ricky Nelson may have had the right idea (in Garden Party) .... " you can't please everyone so you just gotta please yourself"

Diane

[DIANEF]

I get most of my tips for dessing by studying women, usuallly on TV but also when out and about. I browse through magazines, catalogues ect, to see what women are wearing and just as importantly how they're wearing things. I have a look I'm happy with (always room for improvement of course!) and a pretty good selection of clothes, but it would be nice to be able to discuss fashion with my SO, one day maybe...

[Lana Mae]

Yes, I would have to agree the subtlety is amazing!! Take a necklace for instance. How long from choker to a pendant almost to the navel!! Now which is right for when!! How about multiple necklaces-when? What type of necklace-metal, stone, wood, leather, or ???? very complicated!!! Like stated above I tend to observe genetic women to find the answers as well as a few mags. And most are in jeans but have seen some in skirts and fewer in dresses except for church!! "It depends!" Hugs Lana Mae

[Teresa]

Jen,
Lets be honest you love it , like most of us ! Women don't always get it right in fact I've had several comments about how well I put it together.

The point you make is at least you can ask your wife, I don't have that choice so I really have to think it through but that's the aspect I enjoy almost as much as the dressing, the interaction with SAs when buying things it has been so much fun I now prefer to do it alone.

[Elizabeth G]

Unfortunately for me my wife is not available as a sounding board (at least not yet - someday I hope). So crossdressing can be difficult given the difficulty related to the subtleties that arise from "it depends". Especially for someone like me who needs Garanimals for adults, even in guy mode:laughing:

[Nadine Spirit]

I grew up with an older sister who always asked me for fashion advice. It started off with her saying "how does this look?" And my response would be "it's fine." She would then come over, hit me in the arm and say "tell me how it actually looks!" So.... I developed a bit of a fashion sense from this. Of course when retelling the story in my sister's presence, she remembers those situations as not containing the punching portion!

[suzanne]

I have received a lot of top notch tutoring at my favorite dress shop. The SA's there have shown me what works on ME and why it works, so now I'm pretty confident in my ability to put together a nice outfit. I don't rely on any set of rules that sometimes seem hard to understand.

[Rachael Leigh]

I think this is one of the reasons I love dressing is trying to match outfits and accessorizing them too.
It's fun and my wife does ask me from time to time if things look good on her and I'm usually happy to help.

[ReineD]

and while I get the occasional "Yeah, that works," more often than not, I seem to get "It depends," as an answer.

We all have our own rules, within certain bounds, about what is appropriate for what occasion. Other than major conventions (like not wearing a bustier top to church or an evening gown to the grocery store), the subtleties are highly individual. This is why you will see women dressed in a variety of ways when you go to a party. Some will be more dressed up than others, some will have short skirts and some, maxis. Some will be wearing pants and some, dresses. Some will wear a lot of jewelry and some, just a pair of earrings or none.

For the subtleties, it all boils down to personal taste, budget, and the image one wants to project.

And then there is the "sexy" factor: for example, I'd wear a casual, above-knee skirt with flats on a hot day at a Saturday B-B-Q party, but not with high heels on a job interview, if the interview is for a job in a business office. If the interview is as a hostess at a trendy restaurant and I'm in my 20s, then it would be OK depending on the restaurant ... and the skirt. lol. Is it a flimsy nightclub skirt or something that is acceptable for daytime. In other words, we all need to develop a sense of the message we give off when we wear certain things. It's really hard to pull off a, "Wow, look at that hot chick" look, and appear as this comes naturally with no attempt at attracting the opposite sex. If the message is that you're attempting to attract the opposite sex, then it signals that you are available and open to possibilities. And I agree, it takes a while for even GGs to learn this. I made a lot of mistakes when I was younger. In my early 20s, I bought a sexy dress for a fancy company Christmas party that looked great, but my husband thought it sent the wrong message. In retrospect, he was right. He was the boss and I was the boss' wife and it was an office party, not a group of friends going to a jet-set party on a yacht. The dress looked something like this (http://s3.weddbook.com/t4/2/2/5/2255391/deep-v-neck-2015-venexiana-evening-dresses-party-backless-sexy-black-pleated-chiffon-sheath-formal-dresses-gowns-open-back-runway-fashion-online-with-10681piece-on-hjklp88s-store-dhgatecom.jpg), except it was shorter in the front than the back.

Jewelry is purely a question of personal taste (although I agree with Allsteamedup for contemporary fashions) and so is what top goes with what skirt, although it doesn't work to match a winter top with a summer skirt, or colors/styles that clash, or a diamond necklace with a pair of shorts ... but you've been dressing long enough to have developed your own sense of what works and what doesn't? Also, IMO it is so important for people to dress for the bodies they have and not the bodies they want to have. We've all seen men and women dress in clothing that is too small or age inappropriate (i.e. you won't see middle-aged women wearing this (http://www.rantchic.com/wp-content/uploads/2014/10/abercrombie_and_fitch_2012_thumb.jpg), this (http://www.rantchic.com/wp-content/uploads/2014/10/495197365.jpg), or this (http://www.rantchic.com/wp-content/uploads/2014/10/97400344.jpg)).

This is a great article on how to dress your age, IMO:
http://www.harpersbazaar.com/fashion/trends/a10437/dressing-your-age-0415/

[sometimes_miss]

more often than not, I seem to get "It depends," as an answer.
That's because where you're going makes a difference. As does time of day, season, who you're going to be with, who will see you, if you're working or not, etc..

Not to mention, what one woman finds appropriate or fashionable, another might not. There's no simple answer that satisfies all situations.

[Micki_Finn]

Putting outfits together=Shopping=Happy Micki. After 20 years in the retail fashion industry the subtlety of women's fashion isn't too intimidating but I can certainly see how a guy with no experience in women's clothing could be very overwhelmed.

[CONSUELO]

Of course it is difficult. That is why there are fashion columnists and fashion magazines to explore the huge variety of combinations and what works and what doesn't. I enjoy being asked for my opinion and try hard to give good advice.
But isn't it a lot more fun than putting on a pair of jeans and a wrinkled T-shirt.

[Heidi Stevens]

I had no sisters to "observe" and my mother only wore a dress when going to church, so I had to learn on my own. I think over 45 years of trying I got things pretty much under control. My wife knows I have good female fashion sense and doesn't mind me tagging along for her wardrobe selections. She finally acknowledged the other day that her wardrobe is more colorful and stylish than it used to be before she found out about Heidi. I considered this a minor victory, as she usually wants nothing to do with anything Heidi. Just wish I could show her a photo or two of me to prove to her I know my stuff.

[Tracy Irving]

My wife doesn't want me to buy anything she could see herself looking good in. Nothing "trashy" or provocative either. If it fits through her narrow window she sometimes throws in the, "Don't you own something like that already?" Aargh...

[Teresa]

Tracy,
I some times wonder who is better off, my wife chooses not to see me , I started by borrowing her things now she offers sometimes but since going out I've gone my own way and bought what I prefer to wear, it's my style not hers, we are a different shape despite both being a size 10/12. I'm sure my wife wouldn't want be seen in a French maid's outfit, but then I don't wear it that often anymore. I like how I dress now and choosing the accessories , I do have more heels than she does now, which is something I never thought would happen.
Yes I still get sarcastic comments sometimes but that's how she deals with the situation, it does wear thin on occasions .

[Karine]

I also find out that women's fashion is way more complicated than men's fashion and it is why crossdressing is so fun. I now understand why there are so many women fashion magazines. You have to take into account the outfit, the shoes, the makeup, the accessories, take into account your body shape,...

Furthermore, as crossdressers, we do not have a woman's body (bigger shoulders, no hips), so even if we like an outfit it is possible that they don't fit us. For example, when I started to crossdress I bought a strapless top because I always find them pretty. With my shoulders, it didn't look good at all.
Since I started crossdressing, I have made some (rather a lot to be honest) mistakes (wrong purchase, wrong makeup) and realized how much fashion magazines are useful.

Sometimes, my girlfriend like to ask me how she looks, talks me about the last dress she bought or explain to me why she choose this outfit with these shoes and why not these one... Then, she stops, looks at me and smiles and says: "but it is not interesting for you. It is girl talks". When it happens, I really want to come out to her. In a way, the situation is paradoxical: crossdressing could allow us to share something more, but on the contrary it puts some distance between us.

Thanks to crossdressing, I understand women better. I now understand why shopping is so cool for them and why in women fashion you can't just get into the store, take a shirt of your size (with the cut you like) and just pay and go out (This is mainly how I do my male shopping :cool: )

[Krisi]

Women have been "women" for their entire lives so most have a handle on this by now. We have been men all our live and understand the male dressing thing but not the female. I start by holding a skirt and blouse up and looking in the mirror. It's far more than that, of course but that's a start. I have to decide if I want to dress casually or more formal. Casual would be less flashy jewelry than formal.

Remember that "style" caries from one part of the country to another and even among ethnic groups.

The website "People of Walmart" is a good place to go to see how not to dress.

[Jenniferathome]

... but you've been dressing long enough to have developed your own sense of what works and what doesn't? ...

Reine, I have reached a point where I think I have a style that works for me. What's truly challenging is finding the edges of that style. Like any bell curve, moving to the edges presents one with fewer rules and more options. So it depends...;-)

I certainly don't want to become staid. Fashion moves and so should we.

[Sarah Doepner]

Jennifer, for me "It Depends" could easily mean, "for a woman that would work, but not for me". I've been doing this for long enough now that I have my go-to things for public that seem to work okay at not attracting undue attention. However, most of those things don't hit the threshold of feminine enough for me. It's a battle to find the balance between what I want to see and what others will accept without returning to the barn for the pitchforks and torches. ;-) So I guess part of "It Depends" is, as others have said, who the audience is for this particular clothing message.

[ReineD]

I had no sisters to "observe" and my mother only wore a dress when going to church, so I had to learn on my own.

Me too. :)

But over time our sense of what we like or don't like on others around us and in the media becomes more finely tuned. And in my case, over the years I grew to appreciate hand-crafted, artsy things: hand loomed, woven, and knitted items, batik, graphic design on fabric, etc.

[Dana44]

For me I have my own style but I get it depends answers on certain things and she has her style but will make a comment on my style. But we agree on her style and she does help me with mine. As for skirts the blouse is always out but it depends that if it has a good belt line then the blouse should be tucked in. So many rules of fashion that we must learn. But as time goes we do learn a lot and become better dressers. And we say sometimes it depends to her on what she is wearing. It is just a way to get acceptance to what to wear and how things look.

[Gretchen_To_Be]

Reine, I have reached a point where I think I have a style that works for me. What's truly challenging is finding the edges of that style. Like any bell curve, moving to the edges presents one with fewer rules and more options. So it depends...;-)

I certainly don't want to become staid. Fashion moves and so should we.

Hi Jennifer. You certainly have it down. Your outfits are effortlessly blendy and pretty, but I've often wondered what you'd look like in the styles I like. With your fit, lithe physique, I think you would slay.

[NancySue]

You are so right on target. 😉 Prior to dressing, I generally lay out two or three possible combinations. I, too, have a helpful, supportive wife and, most of the time, ask for her opinion about my selections. I, too, get, "it depends", followed by "what about". I believe it's the age old, men are from Mars, Women from Venus. Subjectively vs Objectively. Men want specific decisions or choices. Women's responses are many times, "it depends". When I'm completely dressed, I ask for her help with wig, makeup, heels, jewelry, etc. Our only disagreement involves my wearing hose. I can't remember the last time she wore hose. I know it's out of style, but it's still not fair. I wear hose anyway.