First things first. I am not a thin woman. But this linen dress caught my eye in this color and in a hunter green - and I wish I could budget the money to buy it. I know that if I go to Universal Standard, I'd buy this dress and more.
Since Universal Standard is having a sample sale at this time, I'm thinking of buying the above garment. For me, it will mostly be used as sleepwear. I could also use it as a slip in cooler weather, as it might help me stay warmer while wearing dresses.
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Shopping as a female is an art. As I've said before, shopping as a male is very easy. I don't have to think much, once I have a formula to work with. It is much more difficult to shop as a female, as most women, cis or trans, don't always have the imagination to select garments that would be perfect for more than one occasion. An example of this would be assembling a set of garments to be worn during the day at work, and that could transition easily for a date night/ Not only does a woman's outerwear have to coordinate well, but her underwear has similar requirements. The other day, a woman made a comment to me about the type of underwear she had just bought - just in case she gets "lucky." Even at her age, she realizes that the right underwear can contribute to the image she is presenting at the right time to someone special.
When I first started wearing female clothing, I avoided underwire bras at almost all costs. But I learned that a well fitting bra can make all the difference in a woman's appearance. Now, I wear underwire bras more often than not, as they give better support to my prosthetic breasts than the no-wire bras, helping me to look better in my dresses. The same goes for panties as well. It's both a matter of comfort and coverage - especially when a pre-op/non-op trans-woman has to "tuck."
Once I have my underwear on, then I have to think carefully about what I wear that the world will see. And this is where window shopping comes in. One has to take a critical eye, and look at what parts of a woman's body is highlighted by a garment, and what parts of a woman's body are minimized. Usually, I try to wear sleeved tops without a deep "V" in front. This way, my male shoulders aren't exaggerated, and my lack of natural cleavage is hidden. Ideally I can find garments that give me the illusion of having a feminine waist, but this isn't easy to do. And, I try to wear low hemmed tops, so that any hint of my male equipment is hidden. This makes it easier for me to find bottoms I wan wear and still present a reasonably feminine image to the world.
I am lucky to have the funds with which I can make purchasing mistakes. But if I didn't, I'd be spending even more time learning about female clothing and how it can be adapted to a body which has processed way too much testosterone over the years.