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As I was approaching my 60th birthday, I vowed I would finally go to Ulta and get make up that was geared towards my skin tones. I never really wore anything other than blush, lipstick, and mascara as they are rather generic.
Having been a crossdresser since I was five (my mother told me that my neighbor friend and I used to sit on the front porch and put on my sisters’ old clothes), I got to the point where I wanted to be able to go out in public. I wanted to be able to comfortably go shopping and try on all of the clothes I wanted. Just being able to go into the lingerie section dressed as a woman allows me to feel comfortable touching the delicate items, to pick them up and imagine what they might feel like on instead of the feeling of being a bit of a perv in drab.
I got my courage up one Saturday, and in “Drab mode” I entered Ulta and looked for someone that appeared non-confrontational and open to helping me select the proper makeup for my skin tones. I chose a middle-aged woman, who seemed nice, and told her what I wanted: Foundation, Powder, Mascara, Eye Liner, Blush, Lip Stick and Lip Liner.
She seemed rather shocked and nervous, even more nervous than me, but she got all of the items together except for the eyeliner. She approached an adorable young woman at the Clinique counter, Stephanie, and asked if she could help me with eyeliner.
Stephanie asked me who the eyeliner is for, your wife or daughter. I bravely said, “It’s for me”. Much to my surprise and amazement, she responded with, “I think that’s great,” and high-fived me.
It was truly one of the most magical moments of my life; (I’m not exaggerating). I have always been ashamed and embarrassed about my odd little hobby. For the first time in my life, I felt a huge burden taken off my shoulders. I felt ecstatic and fell in love with Stephanie at that moment.
After I bought all of my makeup at Ulta, I went back the following week and talked to Stephanie (the Clinique Counter Manager) in Drab. I told her that I was wondering if she would give me a makeover, and she said she would love to, so I made an appointment for the following Saturday.
That day, I rented a hotel room near my house and brought over all of my girl clothes and got dressed up as best I could in my favorite LBD. I was scared to death to walk out of the Hotel and even more scared to walk into Ulta, but I did it. It was one of the highlights of my life. I’ve gone back to Ulta dozens of times to have makeovers from Stephanie, who is now one of my best friends and confidant.
Sitting on Stephanie’s stool, in the center of the store, was exhilarating and nerve wracking. I felt hypnotized as she applied foundation, powder, blush, lip liner, lipstick, and eye shadow. I was sitting in the middle of the store near the entrance and surrounded by other customers. I was aware of other salespeople watching me curiously, but I didn’t care. The attention Stephanie was giving to me was more important than my feelings of nervousness and unease at the situation.
Stephanie spent more than 45 minutes giving me my makeover. I felt so confident in my appearance that, for first time in my life, I went shopping en femme. I shopped every store in that strip mall that day and tried on all of the clothes I wanted, never once getting any odd little stares. One man even held the door to Black & White open for me. I did give Stephanie a card with a nice note and a big tip. They don’t promote tipping at Ulta (but everyone there appreciates it), and as long as you buy product the makeovers are free.
When I was finished shopping, I went back to the hotel and took this picture of myself. I used to love this dress.
Well done Jackie, you look really pretty and it is just lovely getting a makeover. I feel so much more confident having my make up done by a professional and I have also had so many lovely conversations sitting there as a woman that ‘he’ would never have. Hoping for many more, Love Linda
Thanks it was exhilarating the first time and now it just feels so relaxing and I love being the center of the make up artist’s attention
Hi JackieBoy,
That’s so inspiring and wonderful to hear of your experience!
I think the Ulta and Sophia consultants get a lot more of us then you think . I remember having to gather my courage my first time, but love to do it now and gather new tips each time.
Bridgette
Thanks I do appreciate the tips. I have gotten so much better in the last two years and getting my new wig at Rorie’s Transformations where I was treated with respect and made to feel welcome was also great
“Darling, you look MARVELOUS"! Very pretty, and attractive, in that dress!
Thanks, I am surprised some what how much I enjoy this attention. It is distracting me from doing my job as I work from home and now feel the need to get dressed up and relax after being out of town all week in Nashville
Very pretty
Thanks, been out of town all week
Hi Jackie: I LOVE your pic in the LBD. I want to do a makeover, too. There’s an ULTA store near me, and if your experience is any indication, I’m sure I’d enjoy it and will look fabulous when they’re done. So, the makeover is free as long as you buy the products there. Is there any minimum you have to spend? Another maybe unrelated question: I have a very nice wig but it needs to be styled. Will they do that at ULTA, or do you have any alternative suggestions? Thanks so much! This will really help me. Hugs,… Read more »
Not sure but many/most Ultas DO have a hair salon area In them so I’d suggest calling one close to you to ask if they will. If not most wig stores provide styling services.
Cyn
Thanks!
I also get my haircut at Ulta and Gail who cuts my hair has styled my wigs for me and she is wonderful, trimming the bangs and shaping it so it looks so much better out of the box. I actually bought a lot of makeup my first time, but I think the minimum is $50, but that is how much lip liner and lipstick costs, not to mention foundation, powder, mascara, blush eye shadow, eyeliner
Thanks, Jackie. My first makeup shopping experience was at Sephora. I ended up buying WAY too much and had to endure a fair amount of grief from my lovely wife, who never spends a lot on cosmetics but always manages to look beautiful. I’ll be much more tightfisted with my money when I do my makeover next month. I hope I end up looking half as gorgeous as you.
Thank you for sharing Jackie! You look fabulous and are definitely a role model. I hope to be as brave as you some day !
-Brie
XOXOXO
I learned so much from Hiedi Phox and Lisa Girl. Their web sites have great tips and tricks and Tips and have helped me develop into the Gurl I need to be
Lovely article Jackie! And a lovely lady you are as well! I’ve done the Ulta makeover experience one and it IS fun. Generally they are quite CD/TG friendly. Thank you for sharing your story with us here!
Cyn
This site is making me aware of how much so many people feel trapped and frustrated by this desire to express their feminine side and I have to become more involved and offer encouragement. Thanks Skippy
What an inspiration story for me. I’m just starting out again and really want to have a consult so that I can figure out the right products for my skin tone. Might just have to do that now… Maybe even dressed…
Appreciate you sharing this.
Shirley
My advice is do it, but maybe take it slow and casual. So many of us feel the need to dress too provocatively and that causes people to stare. First time out maybe just wear leggings and a shapeless sweater to not draw any attention to yourself. Then as the confidence builds and you feel more comfortable fem it up a bit
Thanks Jackie. I’m working up the nerve… I don’t dress provocatively, preferring to wear everyday clothing, especially dresses. Problem is finding said dresses in my size locally. However, jeans or leggings with a nice top might do the trick. It will happen, sooner than later I hope.
Shirley
Yeah, that is was I was trying to suggest is to not draw undue attention to you by dressing a little too over the norm. Don’t draw attention to yourself, blend in
Thanks. Several others have mentioned that very thing. I went out shopping today to find some tops that would work. Lots of sales going on so I was able to get a few things that may work. Long week, too tired to try them on… sigh. But there is tomorrow!
Shirley
You look great, Jackie! I wish I had the courage to do likewise. Some day, maybe.
Start out slow and build your confidence. What’s the worst thing that can happen someone stares at you?
Hi Jackie, it’s Scarlett! I absolutely loved your article and love your look even more than the article. You look fabulous from top to bottom! Jackie, did you steal a pair of my Hanes opaque black tights and a pair of my Liz Claiborne suede ankle booties! Take a few minutes and peruse through my 350 public photos. You’ll see me wearing those same tights and booties with either my wool skater skirt ensembles or my wool Calvin Klein black wool dresses! I love the entire look – the hair color and style, the makeup, the nail polish and lipstick… Read more »
Hi Scarlet, it is hard not to see your pics. Your style is very much like mine, I bought a skater skirt on Amazon, but it was really cheap looking so I never wear it. I really want a Suit with a flared skirt, but never seem to find one at Burlington Coat Factory or TJ Maxx or Stein Mart where I do most of my shopping
Again, Jackie, I loved you in that photo! It was an instant classic. Now as far as skater skirts go, I’ve never seen a wool one that looked cheap so that’s what you have to look for when looking for a really nice wool skater skirt. And with those legs of yours in those black tights with that same pair of black suede ankle booties on or a black suede pair of knee high boots with a wide belt and a snug fitting knit top, you would look like a sexy million bucks! Hey Jackie, I forgot to ask you…What… Read more »
I bought the Booties at DSW about 2 years ago. I like them because they have a 3 inch heel and they are made by GUESS. Tights I have no idea of what brand they are and there are no tags
If they have not tags, they are probably Hanes…That’s how i tell them apart from the ones I don’t like as much.
My ankle booties have a three inch heel to them as well and are extremely comfortable and I could run a 100 yard dash in them!
Don’t forget to Google for “Wool Skater Skirts" or go on Amazon looking for them. Paired with the black tights and suede ankle booties with a wide belt it’s both a cute and a sexy look!
XOXOXO Scarlett
I wish I could wear a wide belt. I have 12 more pounds to lose before I am that weight. I appreciate your help
I completely understand Jackie! Before I do each photo shoot, I have to just drink a lot of water for three days and stay away from the soft drinks and candy! The years are catching up with me rather quickly!