Fashion 101

“Hey, Cheery” I greeted her. “I know, I know. I’m really sorry.I just… could really use your advice. Please?”

“Thank you! Yes, two minutes. I’ll time it.”

“Okay, so. I came out to my aunt and she’s been super supportive, and said she’s taking me out shopping this weekend for girl clothes. I’m really excited, but I’m also kinda lost? I don’t know what to buy or anything.” I rambled on for a bit.

“Right, well, I really like the way you dress, so I was wondering if there were any fashion tips you could maybe give me?”

A pause.

“Please?” I pleaded, “I know you’re not super comfortable about it yet, but I could really use the help.”

“Yes, I know. Just one minute remaining.” I waited.
“Thanks! You’re the best.”

I listened as she started talking, clicketing away at my computer, writing down notes.

“Thank you so much. Yeah, I’m sorry. You’re great! See you then.”

Nearly a full year ago, I was desperately talking to my best friend, worrying and asking for her help ahead of my first shopping trip as a woman. Even then, I could predict a lot of the hardships and some of the joys that would come along with my transition, but one thing I didn’t anticipate, and couldn’t really have foreseen, was how so soon after starting my transition a lot of women would start to compliment my fashion sense, and ask me for tips.

Me. The transgender woman who made it to age 16 before learning the word ‘blouse’ even existed, and age 21 before she bought actual clothing of her own. Hahaha.

Still, ludicrous as it seems even now, I keep getting those comments from other women, which means I must be doing something right.

This post is meant to pass on what knowledge I have about how to choose and wear clothing well. A lot of it is going to sound like orders. That’s not my intention. Everything I’ll write will be meant as suggestion. Some of it will be very strong suggestions, but it will be up to you whether you follow my advice or not. Please remember that.

I also want to be upfront about the fact this post will partly consist of me paraphrasing and copying advice from /r/femalefashionadvice. Some of it will be intentional, and I’ll link to their amazing resources throughout this post, and some of it will be unintentional, since most of what I know comes from that subreddit, so it’s only natural I’ll repeat things I saw there without realising.
If you take anything away from this post, it should be to follow that subreddit and read the great advice other women much more talented than me have written there.

#1 The Basics

Let’s lay down the foundations of fashion, to start off. This is the advice my best friend gave me when I called her last year, though paraphrased quite a bit.

Be comfortable

I don’t care what the world of high fashion says, 10-inch heels which make you want to cut your feet off are not good clothes. In general, the clothing you pick should be the one you feel the most comfortable in. This doesn’t mean wearing band shirts and yoga pants everywhere; the comfortableness should go beyond physical comfort.

Everything I wear, from my skirts, to my jackets, to my shoes, is something that makes me feel confident, and which helps me feel more comfortable in my skin. This is the absolutely essential rule at the heart of fashion. Sometimes I’ll go for something a little more daring, but I’ll wear it on my own terms, in a way that allows me to build up more confidence. Take the dress I pose in on the “Who is Lily” link at the top of the blog. It took me 6 months of keeping it in my closet to feel confident enough to finally wear it out of the house. At first I paired it with a denim jacket hiding everything but the skirt, while nowadays I either wear the denim jacket open, or not at all.


It’s my favourite dress right now, and makes me feel super confident and pretty. I had to work up to that, and the way it makes me feel now is the result of a good balance between daring myself to go for something new and being patient with myself.

The physical comfort part of it also doesn’t mean you shouldn’t ever wear heels, or anything like that. Dressing up now and then in painful but pretty clothing is all right, so long as you’re okay with the frequency of it, and the physical discomfort makes up for itself in mental confidence. The point is that everyday clothing shouldn’t feel like a prison.

Express Yourself

 Fashion is very similar to makeup. Some of the ideas, like balance and colour theory translate from one to the other. In fact, the most important rule of makeup applies very well to fashion as well:

Your makeup (and clothing) should be a representation of yourself. It is a form of self-expression, and is unique to you.

I have a coworker who pairs super small denim shorts with fishnet stockings in a way I could never pull off, and a friend who wears different shades of black so stylishly she’d put a vampiress to shame.

Neither is a look that would look good on me, but which just works for them. Every woman (and man) has their own personality and style. My personality means I wear very fun, happy, girly clothing; for you it might be a bit more geeky, or a little more serious and toned down. That’s great. Embrace that. Don’t try to be someone else.


There’s nothing wrong with pink, but if it isn’t your colour don’t let yourself be pressured into it, on Wednesdays or any other day of the week.

Love it

Finally, and this is less of a concern if you’re rich, only pay for something you absolutely love. I’ve only been doing the girl thing for about 9 months, but I’ve already picked up a few bits of clothing here and there that I just never wear. I’m sure this is the case for pretty much every other woman out there.

It’s going to happen, but try to take steps to minimise it. This advice consists of two parts: Don’t wear anything that doesn’t fit well, and don’t buy the clothes if you feel at all unsure about them. There’s nothing worse than a jacket that rips because you didn’t try it on and it was a size too small, or a pair of jeans that make you super self-conscious everytime you wear them out of the house.

When you go shopping, make sure you try on everything before you buy it. Well, nearly anything. Maybe you shouldn’t try to see how well a pair of panties fits at Forever 21 😛
But everything you can try, do. If anything feels odd or looks vaguely off, leave it. Maybe try it again another day, but don’t waste your money on something you have doubts about. Trust your instincts.


#2 Know Your Type

When discussions about fashion come up, the most common complaint I hear from other women is frustration at how “they are a person and not a fucking fruit.” I always feel a bit annoyed when I hear this, as I inevitably do when I come across ignorance or misinformation, but I mostly just feel angry in behalf of those women because I can imagine all too easily the bullshit they’ve had to put up with that’s led to them hating the idea of body types.

So before we get into depth, let’s clarify a few things.

Discussion about body types, as with everything about fashion, is supposed to be taken (and given) as friendly advice, not commands meant to shame you. A lot of the time people get high and mighty and try to make you feel bad about yourself because of how you look. Fuck that.
Basically, the idea of body types is supposed to be empowering and a basic guideline to give you more confidence and room for self-expression in your clothing.

Graphic Designers are taught not to mix a dozen typefaces in the same composition during their first semester at Uni, to avoid inserting random objects ‘because they look pretty’, and to use certain types of fonts in certain contexts, among other things. All of these rules aren’t meant to make your work lose originality.
Just the opposite, in fact. Having a basic framework of rules to go from allows you to explore your creativity to the maximum, and come up with ideas a lot more interesting and unique than you would if you did whatever you felt like without thinking.
The rules can even be broken. In fact, that’s the mark of a great designer: someone who understands design so well that they can go against one of the basic rules to great effect.

Understanding your body type and the clothing recommended for it should give you a foundation to shape your fashion sense and give you room to experiment and try fun new things without worrying too much that your clothing won’t look flattering.

I’m sorry if you’ve been burnt by people with a fanatic and basic understanding of this, who’ve used it to tell you your body isn’t good enough, or that clothes will always look ugly on you. That’s bullshit.
The advice I’m going to share is meant to help you make your body look even better and build you up. I hope you can take it that way. Without further ado then, here is what I know about it:

What do You Mean I’m an Apple?

Every woman has a body type that vaguely fits her. Note the ‘vaguely’ there; every person is different, and many, many women will have measurements that won’t “fit” neatly into any one type. I do mean every woman, however. Trust me, if someone with the literal figure of a man can find a type that helped her look good until she grew a bit of a figure, you can find a type (or two) that works for you as well.


How do they work, then? Basically, you look at your silhouette or take your measurements and see which of the basic body types resembles you the most. There’s the banana, also known as the ruler, if no part of your body stands out too much. An apple (similar to the more obscure inverted triangle) if you have a bit of a wide shoulder or just thin waist and hips. Pear if your hips are what stands out most, and the famous hourglass if a small waist is complemented by wide hips and a large bust.

There are sites that list as many as 8 types, others 6… there’s no hard and set rules here, but these four are the most popular and so will be most handy when researching.

You can click here for a good post (by /u/thethirdsilence/) on how to find your type, or just Google it, there are plenty of websites that will help you.

What am I Supposed to Do with this?

All right, so you’ve found out you’re an inverted triangle, or a pear, or a kiwi. What now?

Once you’ve found a type you feel comfortable comparing your body shape to, it’s time to research it. Google or search on /r/femalefashionadvice/ to see tips particular to your specific shape.

For example, as an inverted triangle, or a lady with wide shoulders and not much of a figure (though that’s finally starting to change a little… yay hormones!) it helps me knowing to stay away from tops with very thin straps, or bolero sweaters, as they only serve to make my shoulders look wider and less feminine.

It’s important to understand why each type is recommended a certain thing. For example, I often see advice for my body type to avoid colourful tops, and wear neutral ones paired with bright or light-coloured skirts or trousers. The reason for that is that wearing something colourful on top can also highlight my wide shoulders, while something that stands out in the bottom will instead highlight my long legs and the slight hips I’ve been growing out.

However, I love wearing bright tops, so what I do instead is wear a jacket or neutral cardigan to limit the widening effect and get away with wearing what I want. Like I said, it’s a balance between following the rules and knowing them well enough to bend or break them.

If you want a much more detailed explanation of what different bits of clothing do to highlight or play down different parts of your body, read this fantastic article by /u/jkkldfgjklfkl/ on, you guessed it, /r/femalefashionadvice/.

She gives incredibly useful and particular examples of what different types of clothes do for you. For example, a ruffled top can bring attention to your bust, while a full skirt can help your butt stand out a bit more. I highly recommend reading all of her post for other examples.


Apart from all the advice I got from my more fashionable friends and the hours of reading I did online, I reckon a major part of why I dress well has to do with the fact I have a degree in Graphic Design. It isn’t just the fact I’ve developed my eye, but also just how much of design translates to fashion.

When you’re creating anything, whether it’s a book cover, to an illustration, or a poster, you need to look for balance. It’s very difficult to explain, but every good design either balances every element inside it, or purposefully leaves a composition too heavy or too light on one part to create a certain effect. Analyyse anything near you and you’ll see what I mean.

For example look at this poster:


The heavy white space in the top right of the image is balanced out with the “Yo! Bike Mike! Sundays” on the bottom left. I’ll do a post about design principles someday, but essentially, balance helps make something look aesthetically pleasing, as well as making it easier to read (visually as well as literarily.)

There’s also balance with clothing. A ruffled top with a wide belt and bright skirt can look much, much too heavy and work against you, so it helps to balance things out. Wear different styles, know when and how to cut your body into sections, and understand how to avoid visual conflict.

Essentially, this tip consists of looking at your outfit as a whole, and trying to determine whether it works well as a sum of its parts. Something that helps is to unfocus your eyes a bit when looking at yourself in the mirror, and see whether the way your clothing shapes your body starts to conflict with where your eyes are naturally drawn.

A great outfit works like a poem in iambic pentameter; it’s easy to read and feels pleasant, while an outfit that doesn’t have much thought put into it will feel more stuttering and generally displeasing.

Screenshot 2016-02-20 at 22.38.32.png

No, this is not the last time I’m going to link to /r/femalefashionadvice/

If you’re only going to read one article from the ones I’ve linked in this post, please make it this one. /u/schiaparelli/ does an amazing job of translating design principles into easy to understand language, as well as explaining exactly how they apply to fashion, and how you can use them to help you balance your outfits to flatter you more.

Design is more instinctive for me, but her article is great if you’d like something much more specific and useful than ‘go for what looks balanced.’


#3  How to Build a Wardrobe Without Going Broke

In a discussion about dressing better I recently saw someone saying looking good in your clothes is all about having a lot of money.

That’s somewhat true, but you don’t really need a ton of money to build your wardrobe. It’s mostly about patience, and smart buying. Shop in the right stores, wait for sales, etc.

Before continuing, I should state I only have experience building an entire wardrobe from scratch, not modifying an already existing one. In a way, that does back up my claim that you don’t need to be rich. I earn about 600-800 dollars a month, don’t live with my parents anymore, and have had to spend a bunch of money on transition related stuff, yet I’ve still managed to build up a decent wardrobe in 9 months.

So. Here are my tips:

Build Your Basics

When I first started buying women’s clothes, I bought exactly three trousers:
A pair of black trousers, light jeans, and dark jeans. I didn’t buy more until nearly half a year later. Why? Basically (no pun intended) because those three could match with anything I bought, but still change an outfit. I could wear a pair of light jeans with a dark blue top one week, then the same top with my black trousers the next week, and it’d still work, but wouldn’t feel like I was wearing the same clothing.

Let’s take an imaginary scenario. Well start with those three trousers, then do a similar thing with the tops, and buy one white top, one cream a dark blue, and a black blouse.

This is at the heart of outfit-building: if you do it right, three pairs of trousers along with four tops will give you twelve very different outfits.

Build on the Foundations

We’ve got 7 pieces of clothing and twelve outfits. That’s not bad at all, but we could be doing a better job. Now that we’ve got three trousers and four tops, let’s work on building more from those basics. We’ll buy a neutral flowery scarf here, a red infinity scarf there, as well as black and blue cardigans.

Now we have those twelve potential outfits, but each one can be worn with the black cardigan to give us twenty four outfits. Let’s say we only pair the blue cardigan with the light tops. Then we have thirty outfits.

Then you can wear the neutral flowery scarf with all the outfits, with either cardigan or without, and the red infinity scarf with all outfits save the blue cardigan. That brings us up to sixty different combinations, then eighty-four.

To recap, we’ve bought two cardigans, four tops, three pairs of trousers, and two scarves. That’s maybe 200$ bucks for eighty-four outfit combinations. Obviously some of those combinations will be too similar to wear from one day to the other, but if you know how to rotate, you can make it work. Then after that, you can buy a denim jacket, a brown coat, etc and your outfit possibilities grow nearly exponentially.

Oh, and of course, the same idea expands to shoes and purses. Buying black flats, brown booties and similarly neutral purses will give you lots of possibilities.

Screenshot 2016-02-20 at 23.41.58

This chart makes no sense

Work with what You Have

So we’ve got a bunch of basics, a few scarves, and a couple of cardigans. Nice… but it’s nothing special, y’know?

Right. Well, now that we have something to build on (which most of you reading already do, not needing to start off with an empty closet) we can start to spice it up with more interesting clothes.

In this particular scenario, forgetting personal taste, which of the following tops should we buy:
A pink, bright yellow, or red top?

There is no right answer. Whoops. However, pink and bright yellow are the best options, with yellow possibly edging ahead, depending on the shade. Why?

We have to remember the rest of our outfits. The flowery scarf, black cardigan, and all three trousers should work with what all three tops, but the blue cardigan will almost certainly look terrible with red underneath. Yellow, however, would look fabulous paired with it, while the pink top might work with the red infinity scarf. The reason yellow might edge ahead is that if the shade is right, it could pair the infinity scarf as well, while the pink would likely not work with the blue.

If what we care for is efficiency and smart shopping, then the lesson is obvious. When shopping for something, it’s important to keep in mind what we have. If we’re looking to make our wardrobe more interesting with a new scarf or skirt, then it’ll help us if we think of what we already have. When we only have basics, anything new will do. However, once we start to gather more and more unique pieces, it is essential to think of how many other things something will match before buying it.


#4 How do I Know What to Buy?

We’ve established how to start building our wardrobe without going broke, but what do we use our new-found shopping strategy to buy? How can we build outfits? How in the world do I figure out what will look cute and look for it?

I’ll answer that with a question: Have you heard of our Lord and Saviour, Pinterest?


How did people even dress themselves before Pinterest?

Okay, Pinterest isn’t the only thing that’ll help, but it’s a massive part of it. Here, let me go into how I choose what I want to buy and build outfits.


Just like reddit, Pinterest can be used in many different ways. You might use it to pin decoration ideas for your wedding, gather fun recipes, or find DIY projects. The way I mostly use it is as a fashion magazine, to find good tips for makeup and clothing.

Essentially, here’s how it works: I have a denim jacket I like. It fits in a way that feels comfortable, but I’m starting to get tired of wearing it with the same black top and white shirt. What do I do? Why, search for outfit ideas:

Screenshot 2016-02-21 at 00.14.04

These aren’t particularly interesting, but you get the idea. For example, I like the middle one so I’ll look for striped black and white tops. The scarf and belt combo to the left is really cute, so if I happen to see either thing while shopping, I’ll consider buying it.

If you really want to put work into it, you can then look for other outfits you could build with that one item. I really liked the striped top so I’ll search for that.

Screenshot 2016-02-21 at 00.18.48

In case you’ve noticed, yes I AM listening to the Hamilton soundtrack. How did I not listen to it months ago? It’s amazing!

The danger with this strategy is that you’ll find something that looks incredible, like that forest green jacket in the middle there, search for that, and then be sucked in for an hour or two pinning one after another outfit.

You can separate your pins into individual pieces you like and outfits you want to imitate. You might build a specific pinboard for shoes, another for jackets, or scarves, etc.

As a quick aside, if you also struggle with your makeup, Pinterest is a fantastic resource for makeup help.

Back to the clothes. Searching for specific items you have or want to buy is great, but you can also try searching for styles or types of outfits

Screenshot 2016-02-21 at 00.33.50

Damn, Hamilton just turned a hell of a lot more depressing. Phillip 😥

If you see a post you particularly like, you can see the poster’s Pins, and if you like their style, give them a follow. Based on the stuff you Pin and the people you follow, your home page will start to autopopulate with outfit ideas. It’s super handy.

By the by, if you’d like to follow me, here’s my Pinterest 🙂

Also, here’s a /r/femalefashionadvice/ post on how to best use Pinterest.


Again, as in graphic design, so in fashion.

One of the most essential duties you have as a designer is to keep your eyes open all the time, to pick up on design trends by noticing the layout of newspapers, promotional posters, billboards, etc. You’re taught to keep your eyes open, and to developed a cultured eye for picking out patterns, colour combinations, and trends. Naturally, this is one of those things that applies to fashion.

Developing an eye for noticing trends is something you’ll want to develop. Open your eyes and start to notice what other women are wearing. Ooh she has a cute skirt. What top is she wearing to make it work? Aaah, okay. Noticing what others are wearing and how they’re building their outfits will help, and don’t be afraid to outright copy them. If you see a girl at work with an outfit you love, try to note everything they’re wearing, then see if you can build a similar one.

It takes time to get used to it, but once you do, it becomes effortless and you’ll start to get outfit ideas from everything from a walk to the shop to watching Community (seriously, Alison Brie’s character wears the cutest clothes.)

This section is just a fraction of the length of the Pinterest one, but it’s just as important, if not more.

#5 The Colour of Magic

Okay, no, not the colour of magic. We’re not going to talk about octarine, I just needed a catchy subtitle for this section. What we’re actually going to talk about is colour theory.

Honestly, at this point I have to say you should just enrol in a design course at a nearby University for a couple of years if you want to improve your fashion sense.

Jokes aside, this is yet another design concept we’re going to apply to fashion. It’s a subtle field that takes years of study and practice to really grasp, but I’ll do my best to explain the basics.

Colour Palettes

Any composition, whether it’s sartorial, editorial, or photographical, has a colour palette. Simply put, a palette is the colours used. It can be anything from black-and-white, to red all over (sorry).

Seriously, everything does have a certain ‘flavour’ of colours. Let’s take a look at the Mona Lisa:

Screenshot 2016-02-21 at 01.11.19

Palette generated courtesy of

Take a look at the medium colout palette above. It isn’t ALL of the colours of the painting, but it does give you a solid understanding of the feel to the main image. More importantly, the colours work together. It might look a bit dull, but you could build an outfit from those colours. They’re analogous, which means they’re similar and located close to each other on a colour wheel.

Let’s take a look at one of the most famous photographs in history:

Screenshot 2016-02-21 at 01.16.02

Unlike the mostly muddy complete colour palette of the Mona Lisa, Steve McCurry’s masterpiece has a beautiful variation between a rich red and a gorgeous teal that just works perfectly together, in a way that both contrasts and complements fantastically.
Imagine a top/skirt combination with the colours on the fifth and sixth columns on the third row. It would look amazing.

Like I said, everything has a colour palette. Let’s switch to something with a lighter palette:

Screenshot 2016-02-21 at 01.21.28

This one is a little more complicated, but if you look carefully, you’ll see it’s two colour palettes used together. There’s Ellie’s dress matching their picnic blanket, with Carl’s outfit (a beautiful colour combination in itself) matching both the grass and the blanket as well. So, the very bright pink dress, dark grass, and yellow/green outfit of Carl’s works because the blanket ties it all together. The colour palette changes massively, but again, despite being different it’s all the same sort of ‘flavour’. One or two of the colours in the Mona Lisa’s palette might blend into the picnic, but the nearly all of the Afghan Girl’s colours would clash.

When building an outfit, it’s not necessary to match analogous colours, pairing purple with blue, or yellow with orange. You can combine pink and yellow so long as you’re careful and know how to shape the colour palette so there’s an element to tie it all together, and you pick the same flavour of colour, choosing colours that belong in the same family.

How to Build a Palette

Like I said earlier, design is very instinctive for me, and when it comes to colour theory that’s doubly so. However, there are a couple of recommendations I can give.

First off, the Internet is your friend, as always.

From a quick Google search, I found, a site which effortlessly helps you create colour palettes.

Screenshot 2016-02-21 at 01.33.54

I gave it a spin and got this on my very first try. Imagine, for example, an outfit with the black used as the base colour for a pair of ballet flats or trainers, the aqua for a pair of trousers, and a white shirt with some design in salmon on it.

There are dozens of great tools like it. Play around with palettes, and find ones you enjoy.

Additionally, start to observe and, as said earlier, learn how to see. Don’t just limit yourself to analysing the colour palettes other women wear. Look at the ones men wear, as colour isn’t gendered, and really, look at everything in the world. The sign in the subway car, your company’s logo, the inside of your office… everything. There is colour everywhere, and you can find interesting palettes absolutely anywhere.

If you want something more specific than my usual vague terminology about ‘flavours’ of colour, check out this post by /u/pippafilippa on, you guessed it, /r/femalefashionadvice/.


To round it all up, if you want to dress more fashionably, open your eyes and learn to spot colour, patterns, and other outfits, then copy them, or take them as inspiration. Learn how to work your body shape and the ways different pieces of clothing will flatter you. Spend your money efficiently and use basics to build up your possible outfits quickly.

We also learned /r/femalefashionadvice is the single best place you could go for fashion advice. Go there and check their sidebar, maybe leave a post if you want more specific tips.

Over everything else, I suggest you use clothing as a way to express your personality. Have fun and enjoy experimenting. Fashion is supposed to be a fun extension of your personality, not a prison. Break or bend any ‘rules’ you want to if it feels right, just make sure you understand them first, if you want to look your best.

I hope this post has been interesting to read. I certainly worked hard on it. Nearly 6 hours and over 5,000 words went into this. Wow.

I’d really appreciate hearing your feedback on this post; please leave a comment below!
Hope your weekend is going well.

Oh, and if you haven’t already, give my facebook page a follow to keep track of new posts easily! 🙂

Screenshot 2016-02-21 at 02.31.43



5 thoughts on “Fashion 101

  1. Maria says:

    Thanks for this post! I’ve always been into fashion and style, and often have gotten compliments on my personal style. Lately I have felt that my style has gotten a bit boring due to adulting, i.e. having to go to work early. You see, I tend to stay in bed until the very last minute so the time that I have to choose an outfit for the day is not a whole lot… Basically I have some go-to outfits that will be comfortable and nice-enough looking for work. Several years ago I would sometimes build outfits in advance, and come morning I would just throw one of those on. I think I might start doing that now too whenever I have an inspiration. Also, I have been trying to build a wardrobe where everything I have I absolutely love (plus basic pieces to go with everything) but I find it hard to get rid of items that I have… Like there is a dress that I used to love and would often wear it for going out etc. but honestly, I think I wore it last 2 years ago and before that it might have been another 2 years. But I find it hard to let go of it!

    Liked by 1 person

  2. Marta Beveridge says:

    This is incredible. I’ve always admired your style and although I’m quite happy with mine, I’ve definitely learned something new! Thanks for putting so much effort into this 🙂

    Liked by 1 person

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s