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How To Be Super Sexy in a Pencil Skirt

| Oct 17, 2016
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The pencil skirt is perhaps the most classic, most timeless, and most versatile of any clothing item we wear, and for good reason. It accommodates all body shapes, its comes in many styles and colors, it’s available everywhere, and it’s a favorite of crossdressers for obvious reasons, it’s tight. Virtually all of the girls in my Stylish Crossdressers series in the Sister House Dressing Room rock the pencil skirt. However not all of us wear a size 8 and few if any of us have that curvy shape without a little help. And if you haven’t mastered the feminine walk in high heels, well then, you have lost the effect and purpose of the skirt — to be seen as fabulous.


We’re going to tell you how to get there.

And here are the steps:

  1. Know the possibilities
  2. You need hips
  3. Walking the walk
  4. Bringing it together with style

The Pencil Skirt — Sexy and Classic

The pencil skirt was born in the 1940s with Christian Dior but it wasn’t until Chubby Checker introduced The Twist on the Dick Clark show in 1960 that the pencil skirt’s popularity took off. The Twist just involved swiveling your hips back and forth. Part of its popularity was also due to the fact that, since women couldn’t kick their legs out or take very large steps, it was the easiest dance for women in pencil skirts to do.

Imperfect though they might have been from a practical standpoint, a lot of celebrities really embraced the opportunity to show off their curves in pencil skirts. Pencil skirts became a staple of Marilyn Monroe’s wardrobe prompting Jack Lemon to exclaim “Look at how she moves!” when she wore one in Some Like It Hot. Cool fact — Marilyn Monroe’s wiggly walk was actually due to the fact that one of her legs is said to have been shorter than the other. Or because pencil skirts are sexy and they make you walk like a sexy lady! I don’t know, probably the former, maybe the latter.

Once Marilyn was doing it, plenty of other stars known for their sex appeal starting wearing the new skirts. You’ll see them on celebrities like Elizabeth Taylor, Grace Kelly, and Betty Brosmer (a largely forgotten but gorgeous model). Even ladylike Audrey Hepburn got in on the trend when she played a call girl in Breakfast at Tiffany’s. Today they’re a staple for office workers — and thank God, they’re a little easier to walk in than their original incarnation. You’ll see them on celebrities today like Jennifer Anniston, Angelina Jolie, and the Kardashians. They look just as curvy and great in them as Marilyn Monroe did 50 years ago.

elizabeth Taylor and Marilyn Monroe in pencil skirts

Angelina Jolie and Jevvifer Anniston in pencil skirts

The notion conveyed was that the pencil skirt was an item for the sexually confident and sophisticated woman.

Creating Your Silhouette

As we saw in the photos above and those below, the pencil skirt demands pronounced hips that help produce that classic hourglass silhouette. This is the trademark of the pencil skirt look. Obviously most of you agree since my article on Hip Pads…For That Classically Womanly Look is one of the most read articles on TG Forum. Go back and reread it.  The Sugar Love tutorial will give you what you need.

Walking the Walk — The Hip Swing

Women have developed ways to get and keep a man’s attention as they evolved, and this walk is one of them”.  A man-melting stride doesn’t just turn heads —and women who do it are also instantly associated with a slew of positive traits. Um, how  did we not know about this before? Odds are, you’ve seen The Walk or done it yourself without realizing its power: It’s a slightly tamer, SFW version of the Victoria’s Secret model strut. Your head is up, shoulders are back, and you lead with your boobs. Your arms swing loosely back and forth while your hips swivel from side-to-side. Your weight is more in your heels. It may take practice to make it your go-to gait, so repeat this mantra to yourself when you walk: “Shoulders, hips, heels.…”

Once you get it, the stride pays off big-time. The combo of your symmetrical body alignment and rhythmic movements sends a subliminal message to onlookers that you’re in touch with and in control of your body (sexy!). And that makes them assume you’re also in control of your life.


Here are some further thoughts on feminine movement from the TS Roadmap  and some tips from Lucille Sorella on some feminine movement mistakes to avoid.

Your Pencil Skirt Outfit

Now that you mastered the look and the walk, lets listen to Imogene Lampart of and Jane Liddlelow of Style Makeover Hqs  on how to wear and style the pencil skirt. That is followed by a Style Lookbook and a short video on 13 Fabulous Ways to Wear the Pencil Skirt This Season.




Styling a pencil skirt for office wear

Styling the skirt with a blouse (either silky, or stiffer) and statement bib-style necklace adds visual weight to the blouse and connects the skirt colors with the top so the outfit looks like a unified whole. The necklace also makes the outfit more contemporary. Adding a leather jacket and ankle boots with buckles toughens the look. Wear with black opaque tights.

See how swapping the leather jacket for the softly tailored cardigan jacket (on the left) softens the look? Adding black court shoes and nude or sheer-black tights also make the look more feminine, while still being contemporary. This look is suitable for most work environments (providing the necklace isn’t too noisy).



Styling a pencil skirt for casual wear

Above you can see that the blouse can be a colored blouse. The color also needs to provide visual balance with the colors of the skirt. Adding a scarf, in the colors in the skirt, further ties the outfit together. Instead of the scarf you could add an over-sized knit (perhaps a high-low hemline knit) over the blouse. If the sweater feels too full or unstructured tuck some of it in at the front — experiment and see if this works for you. Or see if untucking the blouse and having some of it show under the knit works. All very contemporary looks.

Do you see how adding the thicker shirt and/or heavier knits makes the outfit more casual? Suitable for a weekend day time activity, for instance. Or for a more casual work environment. On the right, is another example with a raspberry-colored chunky knit cardigan and a cami in a similar colour tone underneath.



The secret with pencil skirts is to emphasize the structure of your body and thus you feel comfortable and feminine. Be careful with the choice of material and the length of the pencil skirt, correctly pick the skirt, because it will make your legs look longer and also will hide the unwanted pounds. This season there are popular different types of skirt models, mini skirt, wide skirts, tight skirts, leather skirts all with different lengths and design.

If you usually wear a monochrome skirt, opt for shoes that will make the look complete. For example, with a nice white skirt go brown or black shoes, but if you want bolder combination, then the shoes in intensive colors are a good choice. When you balance the shirt and skirt, the last step is a careful selection of accessories. It is very important not to overdo the quantity. In addition, please refer to our collection and select the model of skirts that best suits your body.


Finally, here’s a down-to-earth interview with Alice featured on the 40 Plus Style blog on How To Rock the Pencil Skirt.

If you have enjoyed this article, please join us and our newsletter at Sister House and Tasi’s Blog and our Pinterest page on Pencil Skirts for many more fine fashion articles for trans women.

And here are a few of our fine stores that sell clothes that fit you

Suddenly Fem     Her Room     Modcloth     Fashion to Figure      Macy’s

And Anytime Costumes if you need that perfect outfit for Halloween (also known as National Crossdressers Day.)

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Category: Style, Transgender Fashion, Transgender Opinion


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. StephanieW StephanieW says:

    Just wanna say, I love your postings…. they are really informative and give complete story…

    thank you


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