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What Outfit Should I Wear?

| Jun 4, 2012
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Wow! What a loaded question, because the answer is “It depends.”  Regardless of age, all women want to feel beautiful and confident. They also want to feel sensual and be noticed, but in a positive way. Now many, if not most of us in the transgender community, would not want to stand out; but we will, either because of our height, our build, our features, or our walk. So the trick here is to be very well put-together so the first glance that we get while shopping in the mall, or walking into a restaurant is an admiring glance, saying “I like what that woman is wearing” and believe me, they will notice, both the good and the bad.

Just today, a CD friend said to me that a couple of her GG friends have refused to go out with her in the past because she is always so put together (hair, nails and makeup, nice outfit, etc.). They tell her they don’t always want to do that, but wouldn’t be caught dead having her look better than they do.

Then how do some women, no matter what their age, so confidently demand attention without seeming to try? The secret — they have taken off the ‘cloak of invisibility,’ by creating their own unique, personalized look that boldly says, “See me.” They are the ones who see their bodies as a blank canvass and their clothes and accessories as their ‘I’m Awesome’ wearable art.

Learning your own archetype fashion style is a key to how you dress and express your own inner self. You may even identify with more than one archetype and create a blend of wardrobe styles. We’ll talk about these archetypes next month, but now I want to set you on the track to two very different classical looks that any of us can achieve and which are knockouts.

I, for instance, love a dress, but look far better in slacks because they lengthen the line of my form. We just need to be flexible in our approach to clothes, knowing that the special look can be achieved when we understand how the elements of fashion come together for the total look. We can become our own fashion icon.

So, let’s look at some possibilities. When building up your attractiveness, it’s enormously useful to have a go-to outfit. For many of us, that’s going to mean a pair of jeans, heels, a blazer, and a bag you’re glad to carry.

Fabulous Jeans Outfit

There are a staccato of choices and almost everyone can find jeans that flatter. Because those sturdy blue trousers have become a cornerstone of American culture, a version can be found for most shapes and sizes. If you are a plus size woman like me, then Lane Bryant’s Right Fit jeans are geared to the size, shape, and length of my body. But J Crew, Eloquii by The Limited, Macy’s, Target, or your favorite boutique all are good choices. Same for heels and blazers — say stiletto, blunt-toe, cropped, or  lapelled.

How do I know this is a go-to outfit for attraction? Very scientific research. Lisa from Privilege puts it this way:  “First, I cast my mind’s eye back over the years, and realized that whenever I felt the time had come to make my intentions clear to a man, I wore jeans, a white shirt, and pearls . . . Second, I reviewed Pinterest. Yep. One of the most prevalent outfits? Jeans, jacket, heels, bag.”

Of course, some of us just don’t like pants. We don’t like the way they feel, the way they look, or both. How then to choose a go-to? Despite Pinterest’s fondness for shorts and skirts and maxi-dresses, I don’t think those are the most attractive solutions. I think it’s got to be a dress. One that allows for movement, but highlights your favorite bits.

Devastatingly attractive, and still comfortable. featuring black leather boots

If you don’t care for pants, it’s quite likely you’re fond of your bosom, as they said in previous centuries. And somehow, with all that leg showing, I think you’re going to want to wear boots for stomping around. For two feet on the ground, there’s little quite as attractive as an effortless, enthusiastic, authoritative stride (and most of us are pretty good at that J).

You will notice, being the insightful lot that you are, a certain Sturdy quality to these outfits. Yes. That’s true. The single most attractive outfit you can own ties directly to your style archetype, whatever that may be. But Sturdies are also quite likely to act as a net plus in your life, i.e., Attractive, so perhaps it’s not only my archetype preferences at play.

You may also notice some androgyny. My theory, until a better one comes along, is that gender testing is dangerous, even today, even now. And those who dare, attract.

Try a little daring. A little stomping. See what transpires.

So, until next month, may you be the beautiful woman that you are.


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Category: Transgender Fashion


About the Author ()

Tasi was a transgender, married, lifelong crossdresser. She passed away in late 2018. She’s the founder of the Ladies of the Blue Ridge transgender group in Roanoke VA, a prolific writer, commentator and blogger including fashion articles for Tri-Ess, TG Reporter, Repartee, and Pretty T-Girls magazine. Tasi currently resides in Merida, (Yucatan) Mexico. Her new website, Sister House and her blog, the Fashionable TG Woman are dedicated to fashion and style for the transgendered woman. Tasi’s book, "Top Ten Fashion Mistakes By Crossdressers and How To Fix Them" is available on Amazon or on her site free to subscribers.

Comments (2)

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  1. tasidevil tasidevil says:

    Hi Sophie,

    There are almost as many recommendations as there are women out there. Here’s an interesting article that might help:
    Bottom line, here are some places to try: Gap, Maceys, JC Penny, Express, Abercrombie & Fitch. Don’t know what might be near you. And don’t forget Zappos. They have an extensive line of jeans and a decent fitting guide. They’re also good for shoes 🙂

    I’m surprised at LB. Did you work with a saleslady? If none of these work for you, come back to me again. In any event, let me know what luck you have.

  2. Sophie Lynne Sophie Lynne says:

    Finding the perfect pair of jeans that fit AND look good?

    My Holy Grail.

    Lane Bryant didn’t work for me. They look like mommy jeans.


    Any other possibilities?

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