6 Fall Fashion Tips For Trans Women In Transition (2023)

As fall weather is (almost) upon us, we begin to refocus and change our wardrobe for the cooler times ahead. Fashion trends today come and go just as fast as summer does, and it can be hard to keep up with what to wear—especially if you’re transgender and beginning a physical transition. And as a transgender woman who can’t get enough of fashion herself, I’m here with some fall fashion tips for trans women in transition.

Of course, becoming so confident with fashion and honing my personal style didn’t happen overnight. In the fall of 2009, I began transitioning when my mom kindly offered me her clothes to wear. She and I have very different body types; she’s shorter with a beautiful hourglass figure, while I’m a bit taller and lankier. Her clothes on my body made me look androgynous, which was a great first step for me because I lived in a cookie-cutter town where no one even knew what “transgender” meant—yet. At first I wore her jeans (which were baggy on me) and her long-sleeved shirts and cardigans (most of which were too tight, too small in the armholes or didn’t flatter my undeveloped chest.)

While my hair grew longer over the course of the next seven months, we bought androgynous shoes, I donned a simple necklace and eventually wore mascara. That spring, I also started wearing a bra stuffed with pads I took from a high school fashion show I walked in. By May, I felt validated and seen for the first time by my classmates when I wore a dress to prom and became the first openly transgender girl to be voted Prom Queen.

During that first year of my transition, there was so much going on for me socially, emotionally, mentally and physically. I had started hormone blockers that winter and the next year I started estrogen. I learned a lot about my body and how hormones can affect your everyday life then. I was excited for the changes happening, but finding clothes that suited how I felt on the inside became uncomfortable and difficult.

I already hated dressing a body I didn’t identify with, and now I had to dress one that also got hot flashes, chest and back acne, easily greasy hair and oily skin. Eventually those side effects subsided, but during the first few years of transitioning, this took a toll on my confidence and general state of well-being.

My friends made me feel better by giving me their old clothes and shoes—but none of those pieces reflected my own personal style. Looking back, I was lucky enough to have my mom there to help style me. And now, after having learned the importance of developing your own unique sartorial identity, I’m paying it forward by helping you navigate your own transition, too.

Here, my top fall fashion tips for those transitioning, plus tons of street style inspo.

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Outfits Can Be As Androgynous, Masculine Or Feminine As You’d Like

You don’t have to fully subscribe to either end of the spectrum. Your body, your choice! When it comes to style, it’s all about color choices, accessories and how you feel from within. You’re dressing according to your style—and not necessarily a gender norm.

Also, I know not everyone can be out at home or in school or both, so starting with simple outfits can be a nice way to ease into this process. It’s important to note that not all transgender people have dysphoria with their genitals; but if you do and would prefer to cover your bottom half, go for it. Again, you don’t have to subscribe to anyone else’s idea of dressing but your own.

And in the fall—perhaps fashion’s greatest season—there will always be classic staple pieces you can’t go wrong with that will have you looking stylish, regardless of how you feel about that sensitive area. Think: trench coats, tailored trousers or a pair of Chelsea boots.

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When in Doubt, A Long Top Over Leggings Is A Great Go-To Outfit

This outfit combo is a great go-to look for these coming fall and winter months—especially if you’re going through hormone therapy. Through this process, your skin will change, becoming easily irritated, oily, and sweaty. I went through this myself and have found that wearing looser and longer fitting tops helped my skin breathe while covering my “down under.”

And as the weather starts getting cooler, leggings with long shirts look great layered under a chunky sweater—a super comfy and stylish look! And if you get hot during the day (which is bound to happen with hormone therapy), just take the sweater off and rock the long-sleeve until you get chilly again. Layered outfits are a staple for fall and winter.

In the same vein, fitted flannels are also great for fall, but wearing a flannel a size or two larger is chic while solving the issues of sensitive skin and coverage below the belt. Again, if you get hot, you can tie the flannel around your waist (just don’t forget to wear a T-shirt underneath!). I actually love wearing my flannel around my waist as an accessory—it adds an edge to my look.

Another outfit formula I love is the classic T-shirt, jeans, and a jacket thrown over your shoulders. According to my (incredibly stylish) mother, Judy Blank, T-shirts with personality are the move. “Tees don’t need to be plain,” she says. “They serve as a great way to present yourself to the world. Graphic tees with a cool quote, beautiful design, or prints and patterns are key to expressing yourself. It’s cool when you pass someone and relate to something on their shirt. What an awesome conversation starter! Don’t be afraid to take fashion risks!”

Additionally, you can never ever go wrong with a black and white outfit. Black jeans and a white top is my favorite fall go-to look. A crisp, white top and dark wash jeans are another staple that will never go out of style.

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Maxi Dresses Are A Great (And Effortless!) Fashion Staple

If you’re ready to wear dresses, there are some amazing fall maxi dresses that are very in right now. Pair these long dresses with boots, a sweater or a jacket and you have yourself an effortlessly cute look that can be dressed up or down.

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Have Fun With Stylish Pants In Different Textures And Silhouettes

Trousers in a variety of washes and colors are an awesome way to have fun with fashion. For fall, I highly suggest dark wash, black, dark green and maroon jeans. Corduroy and velvet pants are very in right now, too, so I definitely suggest getting yourself a pair of each to play up your everyday look.

That said, don’t shy away from fun silhouettes like baggy or wide-leg denim. Of course, leggings will be your lifesaver—they have stretch, are comfortable and can be totally stylish when paired with the right long sleeved shirt, sweater or flannel.

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Autumnal Colors Are Always Flattering

Earth tones will never go out of style. Think brown and beige, maroon, evergreen, marigold, muted blue and burnt sienna. Of course, black is always great for fall and winter. Plus, darker colors are typically way more flattering when you aren’t 100 percent happy with the state of your body.

And don’t forget about textures, too! Satin bomber jackets, off-duty denim jackets and edgy faux leather jackets all give off different moods. Have fun with them!

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Accessorize, Accessorize, Accessorize

With fashion, it’s all about the details. A simple necklace, bracelet or ring can really complete an outfit. So can a pair of sunglasses. Pro Tip: Fit is key! Be sure to choose one that suits your face shape, and not just because it’s stylish or trending at the moment.

Scarves are also a must-have. Not only are they a fashion statement that’s lasted the test of time, but if you are a woman of trans experience who doesn’t like her Adam’s apple or wants to hide it, this is perfect for concealing it—plus, it keeps you warm!

Now that you have an idea of what to wear, I urge you to seek out clothes that will make you feel your absolute best! Remember: This transitional period is for YOU. It’s important to know that no two transitions are the same, so move forward at your own pace. Give yourself time to find your own personal style—it doesn’t have to be right away! What matters most is that you’re comfortable and safe. If you can stay true to those two things, you’ll be on your way to your most authentic and beautiful self. Happy shopping!

A version of this article previously appeared in October 2019.

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