Transition Guide for TS Females

America's Foremost Transgender Woman


The Five Most Common Fashion Mistakes of Transsexual Women

Beating Back the Five Most Common Fashion Mistakes of Transsexual Women

By far, the most common mistake of new transsexual women is adorning inappropriate styles and fashion.

What’s appropriate?

Great question!

It’s not so easily discerned since it depends upon your age, what your body looks like, where you’re going, and what is the time of year / season. Born-girls learn this from their mom’s with that dreaded: “you’re not leaving the house wearing that”. We get left to learn without mom’s stern guidance.

A common challenge many new trans-women must overcome - and the one I most struggled - is embracing not every outfit has to kill it.

Too Much Leg

Inappropriate fashion screams trans like nothing else you could say or do. It also creates barriers to communication with women and sometimes creates unneeded attention from men. I’ve seen more than one trans woman wrongly deduce what she thought was social prejudice - when it was actually just typical female negative reaction to inappropriate fashion.

My most common fashion faux pas’s early-on included:

1. Too Sexy

Notoriously, I opted for showing too much skin early on. At a wild club or Cosplay event? That’s fine and appropriate. However, in traditional social gatherings? I was forced to adapt more conservative fashion.

Nightclub Only

Most of us spent years dreaming of finally wearing those adorable little outfits in fashion catalogs every day we pleased. When we finally got that chance after going full-time? It’s only natural we would first be drawn to stimulating looks.

From a woman’s standpoint: there’s a monumental divide between dressing sexy - and looking erotic. As men? We often didn’t distinguish those lines. However, that divide is very real.

Too much skin

Too Much Skin 1

A short skirt with a nice blazer can be fine: but if I add a cleavage shot to that fashion equation? I’m crossing another line that’s only appropriate for a dark nightclub.

How hot - is too hot?

Good question.

My new rule of thumb?

If someone can look across the room and say my dress is hot & sexy? I probably went too far. If they only recognize that aspect when close-up? It’s probably fine.

Over 40 Short Skirt

2. Age Inappropriate

Without a doubt the most common mistake made by new trans-women – even some long time post-operative females – is adorning “age inappropriate” fashion.

We’re not the only ones that make this mistake. Natal females get tagged for it often, as well. However, we tend to do it more often and play a role in getting us read in public. It will also tend to turn-off potential new born-women friends.

If you’re often shopping in “Juniors” styles as I once was while in my 40’s - that’s the first part of the mistake. In fact: looking through Juniors styles is a great way to learn what not to wear.

This screams inappropriate which in turn spells: “Tranny”.

3. Body and Season Inappropriate

It took me a long time to learn all the aspects of seasonality when it came to women’s clothes. Get it wrong? Women start staring in a hurry.

Event Appropriate

However, my biggest challenge was wearing outfits or dresses that were too tight.

The rule of thumb?

If you wear something considered tight - you need to match it with a loose-fitting garment. Thus, if you adorn a tight pair of pants - you should pair them with a loose fitting tunic blouse

4. Event Inappropriate Fashion

I might have waited two years to finally get a chance to wear my killer new formal gown but if I decide to share it - at an event designed for cocktail dresses? I stand out like a prom queen at a biker bar.

Urban Runway Look

Always ask your hostess what the style is before any event. Even better? Ask your best girlfriends what they are wearing!

5. Inappropriate Hair and Make Up…

Appropriateness or lack thereof isn’t limited to clothes and accessories - it also includes hair and make up. Wearing bedroom eyes at the grocery store combined with some killer cleavage on display can and will get you lots of attention. However, it will also get you read and create a fervor with every natural woman you encounter.

Go easy on the hair extension, hair spray, eyes shadow, blush and full lips for daily activities. The problem with hunting small game with big loads? There’s nothing left to eat even if you kill it.

Wearing too much make up

No Make UP
One of the first big challenges after going full-time is getting comfortable leaving the house with little or no cosmetics. Also, there’s the liquid eyeliner and fake lashes. Conversely, I’ve seen girls too lazy in this regard. The sweet spot is some place between these extremes: a touch of foundation, some mascara, hair pulled up in a clip, a visor - develop a very quick but cute “go to”.

Additional chapters in This Section include:

Fashion and Style Tips for MTF Transsexual Women
Fashion Mistakes of Transsexual Women
Shopping Resources for MTF TS Women
Key to Stealth for Transsexual Women
Transsexual Fashion Tips & Tricks