The Transgender Beauty and Style Mistakes I Wish Someone Had Told Me

Jeffrey Goritz Photography

Since the announcement that Bruce Jenner will be transitioning into a woman, gender identity has been a hot topic in the media. To help other people who are going through this or on the other side of the change, we tapped author Nicola Jane Chase for some advice. The British-born, NYC-based writer transitioned later in life before penning Tea and Transition. Not only is she an inspiring role model, but she also is quite savvy when it comes to beauty and style. Read on as Nicola shares some of her biggest beauty mistakes and how to avoid them while transitioning.

Every woman loves to look pretty. As a transgender woman, those emotions are just as important while we strive to boost our femininity. However, I feel that we have to be more aware of some dos and don'ts, particularly as we never went through female puberty in our teens. I transitioned in my 40s, so what I went through in that decade was what many cis girls (genetic women) experienced when they were back in high school! Yes, I wore skirts that were too short, tops that were too skimpy, and makeup that I thought was on trend but was dreadful in hindsight. There's something to be learned from every fashion and beauty debacle, which I definitely did — albeit 30 years after many others. These are some of the things that I learned as I embraced my transition from male to female.

At the makeup counter
POPSUGAR Photography

At the makeup counter

Let's face it, when you are growing up and greeted by a palette of eye shadow, the first temptation is to do a dash of this color and a smudge of that one, and then round it off with big black eyeliner and a bucket of blush. That's great if it is Halloween, but for most other days of the year, you will come across as a beauty products amateur. That was the same for me in the early stages of my transition. We need to be a little more prudent in what makeup we use and how we apply it.

We are not usually blessed with baby-smooth skin. Depending on genetics, hair growth, diet, age, and goodness knows how many other factors, trans women often need heavier foundations, concealers, and powders. The first brand I used was Dermablend, which worked wonders in giving me a natural base to work with. (It's also great for hiding scars, spider veins, and even tattoos if you need to.) As my skin got smoother through permanent hair removal and hormone therapy, I could switch to lighter combinations. These days, unless it's for cocktail-dress occasions, I'm often happy with a good pressed powder from Sephora.

The next lesson I learned was that earth tones are your friend. Sure, it's great to be experimental with brighter colors, but I always found it a double-edged sword. Did I want people to be wowed by my makeup or not? Yes, it's great to be admired, but I soon realized that in my early stages of transition (when my insecurities were at their height), I preferred to blend in and not stand out. So that meant going easy on the glitter and opting for more neutral tones. Some trans girls were a lot braver than I was at the time, and they went with whatever makeup styles they wanted. But I preferred to be inconspicuous.

Get a makeover!
POPSUGAR Photography | Larkin Clark

Get a makeover!

I remember being dead-scared approaching any of the makeup counters in Macy's and terrified of even stepping foot into Sephora in my early days. What I hadn't realized, though, was that I was absolutely not alone in my fears and also that the makeup professionals in any of the stores are happy to give you tips and advice. If you are still in "man mode" then you can just explain to one of the girls in the store, and I bet you they will be more than happy to help. Likewise if you are presenting as a woman but don't yet have the confidence to dip into the eyeliner rack on your own, don't worry. I have not found one store associate who has been fazed by this, and usually they are happy to help.

If you feel uneasy about just walking up to someone in a store, then you can always call ahead and make an appointment in advance. Most stores will offer a professional makeover either for free or for an in-store purchase of a certain amount. I've done that in Sephora a few times, and even though I was a little nervous arriving and not sure if people knew I was trans, that insecurity quickly dissipated once I sat on the makeup chair and one of the girls started work on my face, explaining everything as she went along. I felt like a million dollars!

Hair today . . .
POPSUGAR Photography | Larkin Clark

Hair today . . .

Hair is one of the biggest concerns for trans women: too much of it in some places, not enough in others. Facial hair is one of the biggest hurdles that we have to deal with, and that means countless sessions of laser, IPL, or electrolysis to get rid of the darn stuff. It's a process that can literally take years to complete, and although there is an improvement over that time, we still want to look pretty during the process. That's where the heavier liquid foundations like Dermablend can really come in handy.

The biggest problem with any sort of permanent hair removal is its expense. Whatever method you use, it is never cheap. If you need to prioritize spending, then I'd always suggest your face is the most important. The smoother that becomes, the more femme you feel. If (like me) you are hair-phobic, then whatever other parts of the body you want to be fuzz-free can wait till you get more of a budget.

The irony of hair for trans women is that on most parts of our bodies we want less of it, but on our heads we may want more! This is often the case for those of us who transitioned later in life. The easiest solution is to find hair products that thicken your hair. Talk with your hairdresser or check online to find protein and hair-thickening products that can help. If you are looking for a more extensive way to fill in receding hairlines or to patch up thinning areas, then hair transplantation is a real option. There are many places that offer this service, but the results can vary, and once again, it is not cheap. But I know some trans women who have done this, and it has truly changed their lives and the way they feel about themselves.

Dressing up
Flickr user Emily May

Dressing up

Clothes shopping is surely one of the greatest pleasures for women, but for trans women it can be tough. Of course, there are trans girls who are 5'5", built with a slight frame, with legs that go up to their neck (some trans models are truly stunning), but most of us are stuck with broader shoulders, minimal waistlines, and flat butts. Can we still look— and feel — femme? Yes! It is all about choosing the right outfits and accessories. The biggest faux pas I made in the earlier stages of my transition was trying to squeeze into clothes that were too small. If I really, really pulled that zipper hard, I could get into a tight top. But what I realized later was that trying to wear clothes one size too small makes you appear two sizes bigger! Sure, some things can be tight fitting, but know your limitations. I am blessed with legs that look good in skinny jeans, but I have to be super careful what I wear as a top or the muffin top returns . . . Yup, just like every other woman!

Again, it's about striking the right balance between feeling good yet acknowledging that everything might not be a good fit. I would love to rock a cute little babydoll dress, but I really don't have the natural figure for it. (And I'm not sure if it is age-appropriate anymore!) Longer dresses, pencil skirts, and sweater tops work far better for me.

To boob or not to boob?
Flickr user Quinn Dombrowski

To boob or not to boob?

Let me first state the obvious: trans women are not born with boobs. I wish I had been, but I wasn't! Some of us may develop something of a cup size if we are on hormone therapy. But if we are hoping for boom-bang cleavage, then we need to know that it isn't coming naturally. That doesn't mean you need a boob job, necessarily — a great bra can really make a difference in the self-confidence department. I found padded bras to be much better than push-up bras (there wasn't a whole lot to push up) to give me the shape that made me look as good as I felt.

Naturally, cis women experience the same cup-sized concerns, while some trans women are perfectly happy not wanting to look like a Victoria's Secret model. I suppose it did seem a little strange wearing a bra initially, but even though I didn't have a classic hourglass figure, it definitely helped enhance my feeling of femininity.

Accessorize, baby!
POPSUGAR Photography | Mark Popovich

Accessorize, baby!

Great accessories can be fabulous in inspiring self-confidence, but as a transgender woman, I also have to remind myself of what I'm working with. The right rings can really add style to a look (chunky ones in particular), but if I go with rings that are too skinny, they tend to make my fingers look fat. Earrings are my fave, and getting my ears pierced early on in my transition was one of the best things I did. Though I had found some clip-on earrings, the choices I have now are overwhelming! And I hardly ever pay more than $5 for a pair of earrings — cheap fashion jewelry is far more fun.

Belts are trickier, though. If I try to wear a skinny belt high above my waist, then it can draw attention to my minimal waistline. It is possible, but I need to ensure that the clothes under it have enough shape to enhance the look. I find big buckles and broad, elasticated belts are more forgiving for my shape.

Shoes, shoes, shoes!
POPSUGAR Photography | Mark Popovich

Shoes, shoes, shoes!

Are you a size 5? Maybe a 6? I'm so jealous . . . I'm at least a 9. That is never going to change, but I thought buying shoes would always be a problem. Nope! I forgot that many cis women have larger feet too, which means most shoe stores have larger sizes as well.

As a trans woman, if you don't feel comfortable asking for a size from someone in a store, try one of the many discount self-service shoe stores. Most cities have them, and it's unlikely that anyone would bat an eyelid when you try stuff on, regardless of how you're presenting yourself at that particular time. There are also more and more online stores that offer free shipping and returns for shoes, so you always have that option.

Again though, trans girls, don't go too crazy on the heels to start with! It is so easy to overcompensate after years of not wearing heels to go for something with an outlandish six-inch heel. Sure, go ahead if you want to, but the danger is that you may come off as drag queen. And that's fine if you are one, but until you find your own shoe niche (which you will, in time), just go a little easy on the stilettos!

So . . . be you!

So . . . be you!

Style, beauty, and fashion can be intimidating for any transgender woman. It took me much trial and error to find the right appearance that I felt good in and that others seemed to like too. Don't be afraid to experiment, but don't worry if you discover that something that you thought would look sensational on you turns out to look like an ill-fitting trash bag. Laugh it off and don't get disheartened; it is all part of being a woman. There will always be something else that works for you and will make you look, and feel, like the woman that you are.

Nicola Jane Chase is a New York-based writer. Her memoir, Tea and Transition, is available on Amazon. For more info, visit TeaAndTransition.com.