Oh, Whatever Will I Wear?

| Mar 12, 2012
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Hi, I’m Tasi and I love fashion. That’s probably saying a lot since I’m an out and about crossdresser, but also a transgendered woman.  No one was there for me in the beginning and like many crossdressers fresh out of the closet, I didn’t have a clue what looked good on me and what didn’t, or where to shop, or what size I was or a million other questions that would help me to be passable and blend in with other women on the street.

Well I learned over time with some help from my very fashion-conscious wife, reading tons of fashion articles, haunting fashion bloggers and all they had to say, and with some incredible help from the ladies in the boutiques where I shopped. Now being a plus-size, somewhat older lady with all the problems of an aging male physique presents its own set of problems, but I’ve managed to still make myself presentable in polite society and even received a few compliments along the way. So Angela has given me the opportunity to share some of those not too secret ways so you too can become the lady that resides inside of you. I hope this is the first of many columns and that you, the reader, will challenge me with your questions.

First, the basics. Number one rule is have confidence. This is a struggle for everyone. Believe me, there are many women out there that don’t have a clue either, and in a society where sloppy has become a norm, we don’t always have the best examples to follow.  But there is nothing that cannot be overcome. I have a dear friend that is a 6’5’’, 200+ pounds prison warden with a manly face, but when made up and properly dressed, she’s a strikingly handsome woman. She’ll never be pretty but she can go most anywhere and be treated as a woman.  “Rejection and embarrassment” are our two greatest fears. That quote came from a size 18 woman. Ladies, this is a big boat we are in.

The next two rules are just here as an introduction and we’ll talk about them more in later articles.  Know your Body — what is its shape (apple, pear, hourglass, inverted triangle, rectangle) and what are your measurements. This critical to a good fit and if you have spent any time shopping, you soon learn that there is no rhyme or reason to the sizing of women’s clothes. Having a good fit is critical to others perception of you. Let that smile that others give be one of appreciation, and not an OMG.

Know your Colors — and stick to them. Whether you are “cool” or “warm” will make a difference in your clothing choices and effect what looks good on you.

In any woman’s wardrobe, there are usually five or six pieces that are considered must-haves if she is to be considered a well-dressed woman.  Nikki Parkinson calls them investment pieces. You may spend more or less on them depending on your budget, but they should be of good quality and they should have that classic look which means that the piece will stand the test of time and not be thrown out to make room for next year’s latest trend.

Foremost of any of these pieces is the proverbial “Little Black Dress” or LBD. Everyone from Macy’s to Lane Bryant is featuring the little black dress in an array of styles and you can follow this link, The Little Black Dress Get’s A Makeover to get an idea of the possibilities. But I would like to talk about taking that LBD and making it sparkle with the accessories that will help you stand out in the crowd as a fashionable woman. There are many benefits to a LBD including it’s a snap to transition from day to night with the dress, it’s less conspicuous meaning you can wear it more often than other colors, it can look expensive when it’s not, it’s slimming and hides tailoring imperfections, and it will always be available on the racks in most every women’s store. So here is a quick video to watch.

One of the best colors to go with black is “red” so here are a few ideas to use red to accessorize your dress.

Use a red bag or wear a red belt or shoes.

Or red lips or a leather jacket    OR    a  “statement necklace.”

Or wear ankle boots for a casual look; go chic like Katherine Heigel; or sexy like Reese Witherspoon.

The possibilities are endless, but keep it classic and change up your look to fit the occasion, and you’ll be one happy lady.


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Category: Style, Transgender How To


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 (3)

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  1. tasidevil tasidevil says:


    Thank you for those thoughts. Indeed, few of us know what all those fashion terms mean and moreso how they relate to what we wear. Peplum, for instance , is often used in suit jackets with fabric extended beyond the waist in an overskirt. You really need to be thin or have an hourglass figure to wear it well as it adds bulk to the hips. I will be treating these various fashion terms in more depth on my own website later this summer….Tasi

  2. besweet besweet says:

    Dear Tasi, I am looking forward to your columns. Heaven knows I need some guidance! A topic I would appreciate your touching on is terminology in fashion and fabrics such as definitions, promounciations and proper spelling of terms like “ruched” and “voile” and “peplum.” What are they? What do they do for your outfit & figure? How do you care for them? Maybe you could cover one or two terms per column. Thank you for starting this series. LYNDA

  3. says:

    Very well thought out piece, Tasi. Congratulations, Ms. Fashionista.

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