Carollyn Faith Olson

Carollyn Faith Olson is the author of several books on Crossdressing Tips and Tricks, a contributor to Sister House, Owner of the Yahoo group, the Mature Woman, and an all round classy lady. She stands at 6-0 ft and weighs 180 lbs. Lets hear what Carollyn has to say about style.

Carollyn Olsen

Interview with Carollyn:

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.” I strive to be myself. 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.

Carollyn in v-neck sweaters and short above knee skirts

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 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 just this summer. I just love wearing them with an assortment of flowery skirts for a more casual look.

Carollyn in prints

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 thought about cross dressing. 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.

Carollyn and Lavern

Carollyn and laverne

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? By 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.

carollyn in different outfits

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? Skinny jeans and a fashionable sweater with a cute belt and heels for the fall and winter. Possibly add a scarf instead of a necklace.

Carollyn in skinny jeans

What would you not be caught dead in? Something that is not me, too revealing and/or makes me look hideous.

What are your favorite web sites?. For dresses: Venus and Sheinside, 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 Named Brand Wigs (up to 50% discount over the local salons). I wear a Noriko Sky. I also love looking at the models at Suddenly Femme. I’m also a representative for Glamour Boutique and a Fashion Consultant for Sister House.

Carollyn in different outfits

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.

17 thoughts on “Carollyn Faith Olson

  1. Pingback: Panties - A Special Pleasure - The Fashionable TG WomanThe Fashionable TG Woman

  2. Carollyn O.
    We have a lot in common; we raised our 3 kids ( now in their mid 40’s) in SOCAL, MISSION VIEJO !
    My medical practice in OC / Faculty at UCI.
    Wespeak on other sites & you always represent “us ” so very well. I appreciate you & your “look ” .I too, try to look my very best when I leave the house. Getting harder ,at our age, to complete with the young Foxes. ..I hope to continue represent in a classy Vintage look. Enjoy being You! T.J.

  3. Love the interview and getting to know about you, Carollyn. And love the way you dress. I can see lots of similarities in what I look for. Conservative, but stylish. I also love JCPenney’s. The majority of my outfits are from them.
    I also love the way you look at things. Someday I will be relaxed and out as most of you girls that contribute to Sister House are. Sister House is my go to web site. I have learned so much and seen that it is ok to be yourself out and about.

  4. Thank you for accepting me as your friend. Now, How do I become part of your site as Caroll, donnakelli and others? I would like to post my story and photos.

    • You need to contact Tasi, the owner of this group. She controls the website. We just contribute. Thanks for asking. Hugs, CC

  5. Hi Carolyn:

    My name is Rita Doyle, from S.California and my comment this time is: Finally! I have found a site I would like to be part of.
    I am also a mature TG who like you enjoys shopping and finding good bargains in shoes and dresses. I live alone and have lots of freedom to become the woman I always wanted to be. you are very attractive. Would love to be your friend. I want to send you a couple of photos



  6. Carolyn, Thank you for such helpful and inspiring thoughts. You are a beautiful woman, and quite fashionable I should add. You have beautiful tastes for feminine style. Your makeup and hair are stunning. You keep your figure in perfect shape. What more can I say but you give girls like me such encouragement to “be the woman we were meant to be”. Hugs and thanks


    • Dear Patrice — I appreciate your comments. I just try to do the best I can with the gifts and blessings God has given me. Thank you, Carollyn

  7. I have the pleasure to be connected with Carollyn on Flickr and elsewhere for a few years and have long admired her as an intelligent lady who really does present as truly feminine with a superb clothing sense of style.

  8. Dear Wilhelmina — Thanks for the nice comments. They are always appreciated. I just try to do the best I can with what I have…and you can do the same thing. Best wishes. I’m here to help. Hugs, Carollyn

  9. it is so nice to read such interview, that transgenders are really nice and serious one and they believe in the natural style. I like yout style and nice pictures All the very best from Budapest Wilhelmina

  10. Right on the mark.
    I will be using some of your key points for my Esprit 2015 co-presentation, Fashion Sense 20.
    The pictures are excellent and tell the story perfectly………..
    Do you find you like to shop solo or with another cross-dresser?
    Would you rather shop in person or on-line?
    How large is Carollyn’s closet?
    If you had to recommend one “fashion magazine” for ideas, tips, etc., which one would you suggest?
    You have to post two pictures: 1. Your favorite outfit, and 2. Your shoe closet!
    Keep the tips coming…….

  11. Great interview from a great person, I love the quote “Be yoursefl and nobody else”. I’ve chatted with Carollyn many times over email and she is truly inspirational and has a good heart. Keep doing what you doing and I am happy to have meet you,


  12. Wow, you look great!!! I am female and am envious. You do look very natural. You have a wonderful sense of style. My thoughts on style are this. Buy very classic pieces. I have suits and dresses 15-20 yrs old and they still look good. They also have not gone out of style.


    • Oh my goodness…I never have read the comments and I’m so sorry I have missed yours. You have given me the ultimate compliment that you are “envious.” I just try to do the best I can with what I have. Feel free to write me at my regular e-mail address. Thanks again, Hugs, Carollyn

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