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 Carollyn Faith Olson  


When it comes to cross dressing, I would be considered a "late bloomer." And, I could "blame" my “evolving” on my cat.

I had often thought about what I would look like as a woman, but never was that interested until one weekend about 35 years ago when I was home alone and working on my wife's dresser. To make a long story short, our cat climbed in my spouse’s nylon box and destroyed a couple of pair. For some reason, I took the shredded hose out of the box and tried them on. Before I knew it, I was wearing a bra, panties, slip, skirt, sweater and wig. The only item I did not have was a pair of heels, which I resolved the following week. I went out in public for the first time a few weeks later and I have never looked back.

I started cross dressing when the internet was in its infancy and most cross dressers were in the closet with no place to go. I had enough problems trying to find shoes that fit, let alone any helpful assistance. I was fortunate to find a limited number of books at a library on the subject to help me on my journey, but it was a struggle. I DIDN'T want that to happen to any one else. Thus the idea was hatched for a series of self-help books.

In the last five years, Ms. Olson has written nine books, including a "Tricks of the Trade:

A Beginner’s Guide To Cross-Dressing” trilogy. All her books are available on Amazon Kindle.  She is also a fashion contributor for Sister House, Glamour Boutique and over 60-ish model and writer for Suddenly Fem.  She also serves as the Post Mistress for the Vanity Club sorority.

Let’s see what Carollyn, also known at CC, has to say about her life.


What is the secret to great style? I’m a very conservative dresser. I just try “to do the best I can with what I have.” Remember, I’m 6-foot tall and 180-pounds. I want to be me and nobody else. I don’t push the limits of my appearance. I don’t show a lot of cleavage, even though I could with certain sweaters or dresses. I love short skirts, but will only wear one if it “works” with the entire outfit and the occasion. I want to look good, blend in and I hope to “be read” as a woman.

What is the one thing you would spend a lot of money on? Shoes!!! I’m a shoe maven. I “must have” a pair of heels to match every outfit. Why I don’t know. I just love shoes. I have only one or two pair with lower than 3-inch heels. However, I always look for sales and seldom pay full price for anything, other than my makeup. Yes, I’m a bargain shopper.

What is the one thing you wouldn’t spend a lot of money on? Gimmicks intended to make me look better. For me, “What you see is what you get.”

How do you balance new trends with a more timeless look? I buy items that look good on me, no matter what the style. If the “latest” fad does not work, I don’t force it. Who decides the “fad” anyway, some designer sitting behind a desk in New York or Paris who doesn’t know me? Why should I try to look the way they want me to look? That’s not me.

My theory is that styles repeat in 20-25 year segments. I still have my first pair of heels and they are just as stylish today as they were over 30 years ago.

What is your current obsession? Flats and skirts. It may be hard to believe, but bought my first pair of real flats last summer. I just love wearing them with an assortment of flowery skirts for a more casual look.

Who inspires you? This is simple. Female Impersonator icon Lavern Cummings, who performed at Finocchio’s in San Francisco in the 70s and 80s. She is my inspiration since I was a teen and first learned about cross dressers. Her beauty, style and total femininity was unmatched. The first time I saw her on television, I was hooked. I have also been fortunate enough to become friends with Lavern and another Finocchio’s star David de Alba, who are both retired in Las Vegas.

Do you have a signature piece or style? I love seasonal V-neck sweaters with just-above-the-knee skirts, belts, and, of course, matching heels.

What’s your secret to making yourself stand out? Wearing classy, stylish and conservative clothes. I try my best to create an image that doesn’t over-shadow other women, but to blend in to my surroundings and the people around me. I believe in wearing what is appropriate for the time and situation.

The one piece of advice most cross dressers need but don’t get? I know I’m preaching, but…”Never over anything”…never over dress, never have breasts that are not proportionate to you body, never wear too much make up, never make a scene if out- and-about…never do anything that is questionable in your thoughts, words or actions. Look like a woman, not a drag queen or a slut.

What’s the best piece of style wisdom you’ve ever received? From my first mentor, JoAn Torres, owner of I Love It Girl in Fremont, CA: “Be yourself and nobody else.”

What is your favorite trend? I love skinny jeans with a fashionable top and a cute belt and heels. Possibly add a scarf instead of a necklace for fall or winter.

What would you not be caught dead in? Something that is not me, too revealing and/or makes me look hideous. Certain colors just aren’t me, like green, grey and gold.

What are your favorite web sites? For dresses: Suddenly Fem, and Venus although I buy most of my clothes at the local Macy’s or JC Penney. For some reason the styles at Penney’s fit me best. For shoes: Anywhere where I can find size 11-12. For wigs: The internet site Name Brand Wigs (up to 50% discount over the local salons). I wear a Noriko Sky in Sandlewood (a rooted blonde look).

How would you describe your personal style? Conservative, but stylish. I want to blend in and not stand out. I love dresses, jackets, sweaters and skirts. I don’t enjoy wearing blouses, except for one sexy black top in my wardrobe. I strive to wear what other women wear when they are out and about.

Who are your style icons? Lavern Cummings will always be my favorite. She could make any dress look good. Other than Lavern, not really any other female stands out, maybe because I’m just good ol’ me and can’t be anybody else.

Click on Carollyne’s portrait below to go to her Flickr page.