As a friend of several trans women, I am often asked this question by ladies before they venture out in public. Throughout the years, I have been fortunate enough to have trans-friends; I have learnt some very basic lessons as to what works and also what lets people down. I also advise and correct ladies when asked to photograph them, giving (hopefully gentle!) guidance on how to look as feminine and gorgeous as possible.
Of course, transgender people often dress for entirely different reasons: without passing judgment on why people dress, this article is aimed at those who wish to look as feminine as possible rather than draw attention to themselves because of their transgender status. This article is written primarily from the perspective of male-to-female transgender persons, but many of the concepts would apply to female-to-male persons, too.
1. Dress in an appropriate style for what you are doing or where you are
A naturally born female will stand out if she is wearing something inappropriate for the activity or venue. She will look out of place wearing club wear in a supermarket or jeans and a t-shirt at a black-tie event. The same is true for trans women. A good question to ask is, what would a CIS female wear? So, for example, if you go shopping, wear jeans and a t-shirt or an everyday dress.
2. Don't overdo the makeup!
The same goes for makeup. Makeup should be appropriate for the outfit, venue and activity. Many transwomen go over the top with makeup so that it doesn't look natural. Of course, use makeup to disguise and cover the male features of the face, but keep it subtle! For most everyday activities, women wear little or no makeup. Smokey eyes, long fake eyelashes, thick blush and bright red lips draw attention unless you are in an environment where other women will be dressed likewise, such as a wedding reception.
3. Pick clothing & accessories to give a female shape (and disguise male features)
CIS females will often pick clothing to accentuate parts of their body they wish to show off (maybe cleavage or legs) and to disguise their less attractive features. The same applies to trans women, with the added complication of the need to consider their male features. Let's think of some basic issues:
If you are unable to shave, cover up unshaven areas, including legs, arms, and chest. I have seen otherwise very attractive ladies wearing stunning dresses with hair coming out around the cleavage!
Pick clothing that disguises the male body shape: especially around the shoulders, neck, waist (men do not generally have a waistline in the same way as women) and muscle areas (especially if you work out). Pick clothing colours and designs that give the illusion of a more female body shape. This can include waist-clinchers and corsets, but it can also include shaped jackets and dresses like the classic skater-style dress.
Shoes: while many trans women adore heels (and I fully understand their feminine allure), they add to your height; if you're tall, you may need to opt for flats or small heels when out in public (or find a very tall date!).
Don't forget to accessorise! Accessories can either cover or draw attention away from male features. Scarfs are a very useful (relatively cheap accessory) that can add style and cover the dreaded Adam's apple. A long necklace can help create shapes around breast forms and draw the eye away from the neck area.
Invest in the right wig! There are many differences between the stereotypical male and stereotypical female face. Picking the right wig can help cover, break up and draw attention away from the more prominent male features. One big difference is the forehead; a nice sharp fringe may look fantastic on a female-shaped head but typically draws attention to the male forehead; generally, it is better to wear a wig that breaks up the forehead. As this is the one item you'll be wearing all the time (no matter how you are dressed), it's well worth investing in a decent wig that helps with the female illusion.
4. Develop female mannerisms (and avoid male ones)
A naturally born female will stand out if she is wearing something inappropriate for the activity or venue. She will look out of place wearing club wear in a supermarket or jeans and a t-shirt at a black-tie event. The same is true for trans women. A good question to ask is, what would a CIS female wear? So, for example, if you go shopping, wear jeans and a t-shirt or an everyday dress.
5. Be confident
Trans women may be naturally nervous out and about in public, especially if they are new to being out and about or do not get the opportunity to do so regularly. However, appearing nervous or uncertain often draws unwanted attention. Although inwardly you may be shaking, try and be confident; don't dither about picking a seat in a cafe or buying clothes in a shop.
