This was in reply on facebook to a friend asking about how to build a personal fashion and style sense.

OMG. So I’ve been trying to figure this out for myself for the last two years. For me it’s becoming a balance of four things:

1. Comfort. I mean if ain’t comfortable, I’m not going to bother with it for everyday wear.
2. What feels empowering. If it ain’t helping me sharpen my knife in the morning, it ain’t worth it.
3. Do I like how it looks? I mean…I tend to have rather specific aesthetic preferences. So if I hate it I’m not going to be comfortable or feel empowered. But if I like how it looks, I’m gonna be willing to take some more effort—at least when I really want to shine.
4. Does it tell me the story I want to tell myself? This one is hard to describe. I tend to dress super femme these days—which is a thing a lot of transwomen do especially at the beginning of their transition because clothing and style is a form of social communication. And this is kind of hard, because there are a bunch of difficult (and honestly problematic) social constructs around what the way we dress says.

To help give myself a framework for thinking about navigating everything, I kinda created rules and a brand style guide for what I want:

First is fully understanding and acknowledging that appearance, clothing, and feminity are complex social constructs embedded within systems of oppression and liberation. And what can be liberating in one context can be oppression in another (eg shaving one’s legs). So I hold both thoughts in balance with one another when I’m making choices.

Second, I focus on things I want to say to myself when I’m choosing an outfit. I’ve kinda built a brand and tone style guide for myself. I come up with words and feelings I want to evoke for myself: scholar, liberation, grandmotherly, gravitas, teacher, worldwise, &c. I try to imbue meaning into my choices, maybe the pattern or colors have meaning (prints with flowers and plants are particularly meaningful to me since I grew up on a flower farm). Before transitioning, I intentionally chose to dress a little like a professor or architect with bowties—I let them carry over in my accessories and dresses with sashes and bows. Similarly, I intentionally choose things that are a little stereotypical of schoolteachers in the 50s and 60s—so like Katherine Johnson in Hidden Figures, who was a school teacher before going to NASA. As an aside, Katherine Johnson used to make all of her own clothes and the costume designer found old patterns to dress Taraji, so when she saw the film, Katherine mentioned that she recognized a lot of the patterns Tarji wore.

So to go back to the third point, I take a somewhat historical view of choosing an aesthetic and style: I’ve always had a thing for the stuff that came out of the late-40s to early 60s with Dior’s New Look and some of the stuff that came after: so peplums, curves, peter pan collars, and A-lines. So a lot of post-war stuff where educated women were finding a new place in an increasingly connected world and the beginning of the civil rights movement.

As a practical matter, I also cheat by following a few rules to fight choice overload:

1. I generally keep my wardrobe and accessories to a few color palettes I know work together so I don’t have to think that hard to put things together. (It’s hard to go wrong with jewel tones.) It also helps establish a consistent visual brand that people recognize.
2. Instead of having the entire world to choose from, I artificially limit my choices. Since I tend to dress from what a lot of folks would call vintage styles and patterns stuff from a lot of chain stores with modern aesthetics are out for me, but also I try to limit myself to places I know with good human rights practices…which severely limits my buying power (fast fashion is cheap because of human rights abuse and environmental degradation)—but it also means that I’m not overwhelmed by infinite choices.
3. Dresses are half the work but make you look twice as put-together.
4. I have particular lines from brands that I like. For instance, since I often wore bowties before transitioning, I kinda carried that over with Kate Spade’s bows for necklaces and other accessories. It’s totes okay to be consistent in the things you like—it makes decisions because when you have a few pieces that fit with all your other pieces, that multiplies how many outfits you have rather than adding outfits one set at a time.
5. When I find one piece with a pattern (shape/silhouette) that works well on me, I will look for pieces by the same designer that uses the same pattern but with other designs and fabrics. This saves so much time on trying to find pieces that fit properly. While a size 14 from the same brand might be different across patterns, if it’s the same pattern if one fits, the others do, too. And they’ll in a similar style which means your accessories will probably work across outfits, too.

And a part of this is totally about justifying things I liked anyway. But I find that having stories to tie it all together helps build a framework for making conscious choices rather than just trying to wander around looking for something that catches my eye.