For the one year anniversary of our Eye Candy Girl relaunch, we turned things up a notch. Or 10! Not only are we featuring our Anniversary Girl, but we have some extra special Eye Candy as well. As part of our dual Glamour Girl Grand Champions, Tippy Gillette took the contest by storm winning it all in her very first year as an entrant. This Super Cougar lets us all know that age is just a number. After her big win, we sat down with Tippy so all of her fans can get to know her better.
Congratulations on becoming this year’s Co-Grand Champion. How does it feel?
It feels wonderful! I am surprised and delighted that I am chosen to be Grand Champion. I dreamt of winning the Glamour Boutique Picture Contest in the Super Cougar category, but now Grand Champion seems like the gift that keeps on giving. This is a precious validation for a girl that never thought of being honored in such a way and something that will stay in my memory for a long time. I am grateful and pleased that I could be considered and awarded as such.
Can you tell our readers where are you from?
I grew up in the Midwest, more precisely in the Chicago suburbs. After college I lived on the north side of the city in/near “Wrigleyville.” I was born in Oak Park and went to school in central Illinois. I have been in southern California for all of my adult life and today I live in Palm Springs.
When did you first start dressing and how did it come about?
Like the stories of many others, I felt the need to dress at a very young age. I was perhaps 6 or 7 years old when I would sneak clothing from my mother’s dresser and use rolled up socks to plump my breasts. I hid my activity from my parents and their disapproving eyes. When I visited friends’ homes where girls lived, I’d test high heel shoes on my feet when there was no one to see me and that felt good, especially seeing myself in a mirror.
How did you come up with your Femme name?
The internet was new in the early 1990s and suddenly there was online messaging and chat rooms for shared interest groups. Cross-dressers were open and available to meet online. A world that I didn’t know existed became apparent. And, having opened up to my closest personal friends and starting an online internet hosting service for trans persons, I was presented with the need to call myself something. I wanted a playful name because that’s how I see myself. So I played with word sounds and “Tippy” sounded light to me. There is also the very sexy and vivacious actress Tippi Hedren who came to mind that I admire for her acting and her looks. But instead of Tippi, with a little change of spelling I adopted the girl name Tippy. I had T and wanting a G last name would make my initials “T.G.” That’s appropriate I thought. Then trying names starting with “g” I finally hit on the name “Gillette” which is French. Tippy Gillette. French? Maybe. A stripper? Could be, but not necessarily. Perfect. TG for short. Who can resist? – “Ooh la la”
How often do you dress?
I have over time dressed daily, weekly, monthly, or not at all. Recently I dress often, but not always to go out. And many times I’ll only wear a few pieces of clothing – a top, shorts, shoes.
Are you married/in a relationship? If yes, are you able to share your female self with your partner?
I have married twice. Not at the same time. LOL. I explained my crossdressing to both wives in the very first days of what became growing relationships. After 25 years of being in the closet, I decided that if the relationship couldn’t survive a full disclosure, that I would not bear the danger or stress of secrecy and possible disappointment if that open knowledge produced strife.
My first wife was accepting and relieved that I shared my truth, but years later as I became more active in my cross dressing in going out with friends, she became more resistant and I became restricted in keeping my cross-dressing to myself. We separated and eventually divorced.
A week or two into the relationship with my current wife after I opened up to her about Tippy, she took a couple of days to think about my reveal and decided to go for it. She enjoys my dressing at times, is supportive with advice, my socializing with my sisters and discussions. She is an exceptional person in her unconditional love. I love her very much and we work at staying open to each other’s changes.
What are some of your favorite outfits/fashions?
I like tight fitting and bodycon clothing. I only look bigger when the clothing gets flouncy or layered. Keeping myself slim and wearing sexy clothes and knowing what body parts need cover and what parts need exposure is learning about my body start to finish. I like my legs but they can look too skinny, so wearing shorter skirts and showing thigh, I look better than showing only ankles or calves. My shoulders are wide so dark tops and tight tops keep the appearance of my top body width in check. My body is pretty straight up and down so tops that flare at the waist or wearing corsets give me more shape. A little butt padding is nice in jeans and tight skirts. Larger hip pads give me shape but make me look bottom heavy, so thin pads work best on me when I wear them at all.
Stockings or pantyhose?
Heels or flats?
HEELS! I like a higher heel. My legs just look better with a 4.5 or 5-inch heel. People ask incredulously how I can walk in high heels. I always answer, “practice, practice, practice.”
Good looking shoes in my size are hard to find. Shoes are so important when it comes to how they are styled, cut and put together. I find it difficult to find nicely tailored shoes in large sizes unless I have them custom made, which can be pricey. I am so jealous of girls that can wear size 11 or smaller as there is SO MUCH MORE CHOICE of quality, patterns and styles in smaller size shoes (especially now). But it does take searching, shopping and research to find what you like. Years ago, heels in size 11 were rare!
A Spanish company called Renetti made the most delicious leather shoes in large sizes, but alas, they are gone from the business. They produced a classic ALL LEATHER pump that was high heeled, low cut, precisely stitched and expertly made. Their shoes wore forever, were reasonably priced and were comfortably fitting too. I still have one pair tucked away for occasions.
Heels – definitely a sexy look.
Favorite places to go when dressed?
I’d prefer to be in more general places than in a club or a bar. Clubs are fun, too, but I like to push the envelope a little, even if I get read right off the bat. And I enjoy the company of other cross-dressers as I have no need to explain what I do. I have met the most fun girls.
I like to go anywhere when I’m dressed. I enjoy going out to eat, films or events. I have my sister friends to thank for places to go. I go to restaurants, shows, wine tastings and such. While I’m not likely to go alone like some girls, I will still go out on my own on occasion.
I’ll go to a club with friends, but if given clubs/bars as my only entertainment, I find that gets old very quickly unless the people I’m with are the main event.
Go to accessories for a night out
My favorite items are certain pairs of earrings and necklaces or bracelets. I wear clip-on earrings as I haven’t pierced my ears yet. Scarves that I have are great to drape the neck or shoulders and create a softer look for a splash of color. Nothing looks more together than when I have a nice bag and matching shoes. And anything sparkling like a bag or jewelry, silver or gold, makes me feel special.
Who is/are your female role model(s) and why?
I love Annette Bening. She is SO beautiful and SO classy. I met her one evening a couple of years ago while in boy mode and she was as gracious and friendly as can be imagined.
Do you have any hobbies (either when dressed or not), likes, or things you do in your spare time?
I like hiking and being outdoors. I like to sunbathe nude by the pool. I love my photography work and especially enjoy cooking. Once in a while, enjoying a cigar under a mesquite tree with a glass of whiskey is unbeatable. Tippy doesn’t smoke.
Any stories you would like to share about yourself and your journey?
I am a fetishistic TV. Look it up. So, I dress most often for my own entertainment.
Growing up with my secret taught me to accept who I am, even when I couldn’t share. The denial of self-acceptance is to live in constant self-judgment and doubt and hinders me from all that I can be.
Now, older (and better dressed) I am enjoying myself out and about and learning that I can never guess how people will react to me and my appearance. I am surprised by others in their reaction to me, good and bad. But either way I smile inside, laugh a little, knowing that who I am in the moment is always me.
If you have social media, what is the best way for others to follow you?
I can be found on Facebook (https://www.facebook.com/tippy.gillette).
If you would like to send a message out there to your fellow girls or a closing statement.
There is nothing more attractive in a woman than an authentic, natural smile.
Thanks Tippy! And Congratulations on your big win this year. We look forward to seeing more of you in the future!
As we enter our second year of Eye Candy, we are so excited to hear more stories and get to know some of our girls better. Thanks to all of you that have made our Eye Candy features so popular. We could never do any of this without you!