How to Develop Your Personal Style

The most gratifying thing happened to me the other day.  In a group text with three of my girlfriends, two of them said they had been talking earlier that day about, and I quote, “how jealous we are of your dialed-in personal style.”  They then asked me how I figured out my style.

This is a hugely validating compliment for me.  Even a few years ago, I don’t think anyone would have said I had a “dialed-in personal style” because I frankly didn’t have one.  Like many people, I spent most of my life struggling to have any style, much less a personal one.  Over the last few years, however, I’ve noticed that I in fact do have a personal style now, one I am very confident in and actively enjoy.

So, I sent back three blushing heart emojis and started explaining.

Pay Attention to Yourself

The single most significant reason I can give for how I developed my personal style is that I have made a real effort to listen to myself, to notice when something doesn’t feel right to me or when something feels SO right.

When I reflect on my relationship with fashion and dressing myself over the years, it’s obvious how often I ignored my intuition, my discomfort or displeasure with a particular cut, style, color, and so on.  We’ve all put on an article of clothing that we felt like we should be wearing and been miserable in it.  Our misery could be because it itches, because it’s too snug, because it’s a displeasing color, a less than awesome print, too modest, too revealing, too boring, too whatever.

Hindsight is of course 20/20, but looking back it’s easy to remember how uncomfortable I felt as a high schooler in the early 2000s who thought she HAD to wear low-rise jeans. Or in my late 20s trying to make casual athleisure outfits work when I just felt naked and exposed.  Or religiously wearing heels to work, ignoring the pain all day long.

Energetically, I fully believe that when we are distracted and uncomfortable, even if we are wearing the coolest outfit around, we will project our discomfort more than how cool we look.  People pick up on these subtle energies.  I think that’s a large part of why my friends even notice my style; because I am so into it myself, they pick up on the confident, comfortable, feeling myself energy I emit.

Forget About Trends

One key to developing personal style that may only be possible with age is not giving one single fuck about trends.  I spent much of my life, from preteen years through my 20s, focused on fitting in and being as fashionable as my meager resources would allow.  That meant following trends, trying, and often failing, to adopt them.

Following the latest in fashion is a great hobby and passion for many, myself included.  I fully encourage it if that’s what someone enjoys.  But it’s important to see trends as a take-it-or-leave-it offering from the world of fashion, not some decree from on high about how we should be dressing ourselves.  Fashion and style are at their core creative forms of self-expression.  If we’re all just copying what other people do, that self-expression is obliterated.  Instead, we can follow fashion for inspiration, integrating parts that resonate for us as individuals.

Trends are often caught up in specific items.  In elementary school, the coolest thing to wear was either an Adidas or Starter jacket.  In middle school, everyone wore mini butterfly clips (yes, I’m a millennial). In high school, we started to see a bit more individuality, but there was still a huge trend to wear three polos and pop all the collars or layer a bunch of tank tops and see all the hems (what on earth was happening in the early 2000s, I ask you).  In my 20s, living in a big city, it was all about the latest sneaker.  Nike Free’s. ON running shoes.  Allbirds.  You get the picture.

Now there’s nothing at all wrong with buying trendy items.  What gives me pause is feeling like you must buy the latest thing to be cool, right, valid, or some other iteration of these related feelings.  That’s consumerism talking, driving us to “keep up with the Joneses” by buying another product that promises to be a “solution” to our “problem” of not being enough. 

I recently bought one and then two more of the Stanley tumblers that are all over the place with influencers lately.  I learned about them because they are a trend, but I decided to buy them because I personally loved the colors and they satisfied something I’d been looking for over the last few years – an aesthetically pleasing water bottle that was huge and fit in a car cupholder.  I didn’t buy them because they are cool according to the internet; I bought them because they were cool according to me.

The flipside of this is recognizing when something is beautiful, cool, or super neat, but just not for me.  I have seen many examples of beautiful trends that I absolutely love, but that don’t fit with my style and needs.  Does that neon-yellow monochrome outfit I just saw on Instagram look incredible on my favorite plus-size model/influencer?  1000%.  Would I like it on me?  Nah.

UnLearn Style “Rules” and Body Image Bullshit

I had to do a lot of unlearning style “rules” I heard regularly growing up, particularly the concept of anything being “flattering”.  “Flattering” is often a heavily coded word where the person using it actually means “slimming” or more bluntly, “this makes you look less fat.” As such, it is inherently anti-fat, implying that appearing to be fat is a terrible thing, something to be avoided at all costs. 

Some examples from my own life: aside from about 6 years when I had an eating disorder, I’ve always been fatter or at least in a bigger body than my peers, so of course I heard that I must wear black and that wearing white was an absolutely terrible idea on my body.  Horizontal stripes?  Unless you want to look as wide as a house, absolutely not. I have brown hair and eyes with pale skin, so for some reason complete strangers in stores often felt the need to tell me I should wear jewel tones.  All of this “advice” is utter nonsense dispensed with the intent of telling people to fear their bodies.

The reality is that some people are fat.  There have always been fat people and there will always be fat people.  Fatness is also morally neutral, despite society’s best efforts to insist otherwise.  Dressing with the express purpose of hiding aspects of our body is to invoke shame daily.  Regularly stepping into this shame mentality is poisonous and can lead to body image issues and more.

When I choose what to dress myself in, I want to make those decisions from a place of joy and self-nurturing, not from self-judgement and shame.  All bodies are deserving of comfort, care, and style, not just thin ones.  So, fuck flattering, at least in this usage of the term.

Choose Your Color Palette and Print Preferences

A somewhat obvious place to start noticing what you enjoy and what you don’t is with the colors you wear.  It feels obvious for me, as I am a very visual person who has always had a strong response to colors.  Looking at certain colors, I feel a little thrum of pleasure in my body.  As a teenager, my love of color manifested in increasingly funky nail polish colors I could stare at in class.  Also, all the gel pens.  All of them.  Now, one look at my closet and you know exactly what my color palette is.

Over time I realized that whenever I wore black, my body and spirit felt heavier.  Even if I looked good in a black outfit, I didn’t feel good in it.  The simplest way to explain this feeling is that black just didn’t feel like me.  Honing my sensitivity to that feeling led me to discover more preferences I had around color.  I realized I didn’t enjoy most saturated tones, preferring softer hues instead.  For example, instead of a Kelly green, I would prefer a sage.  Incredibly cheerful colors like yellow and bright pink also felt off for me.  I’m a bright and sunny person, but bright and sunny colors were never ones that gave me that thrum of pleasure when I looked at them…so why would I want to see them on my body all day? 

From there, it didn’t take long for me to establish that I most love wearing what I call desert neutrals.  My closet has lots of cream, white, certain blush/rose colors, all varieties of rust, so much sage and other soft greens, and all the shades of brown.  For my version of a pop of color, I have deep periwinkle and soft chartreuse items that set off the core colors in my wardrobe so well. I have very few print items and almost all of them are subtle floral patterns.

Since literally all my clothing fits into the same color palette, the combinations are endless. I’m constantly discovering new favorite outfits from the same clothes I’ve had for ages.  Getting dressed is MUCH easier when you’re not struggling with making new colors and prints work together.

Knowing what colors you love also makes shopping easier.  When I used to find articles of clothing that I liked the cut and feel of, but didn’t come in a color I loved, I would buy the item anyway and agonize over making it work.  Of course, it never did work and would eventually be donated.  Now, I just don’t buy clothes I don’t love!  It’s obvious to me now that compromising for clothing is a waste of money and energy.

You can rely on your color palette as a grounding place from which to start your search for a new addition to your wardrobe.  Think about shopping for a new item for a specific occasion.  Usually those are higher stakes moments when we want to look and feel our best.  If you start looking by colors that you already know you look and feel great in, that makes the search process so much easier.  Sticking to this palette can help you feel more confident in whatever you’re wearing.

If you’re not sure where to start, there are also many color consultants out there.  If you’ve ever heard of “getting your colors done”, color consultants help you develop your personal color palette.  They use a set of metrics related to color theory to help determine which colors complement your skin tone, hair, eyes, etc.  I know quite a few people who have had their colors done and swear by the process.  My only advice would be to still leave room for joy – just because a color isn’t in your prescribed palette doesn’t mean you can’t ever wear it.

Understanding My Body Proportions

There is one definition of “flattering” that I find extraordinarily useful, and it has nothing to do with looking thinner.  When I say something is “flattering” these days, I mean that it highlights my natural shape in the ways I like to do so.  This is a subtle difference, but an important one.  The anti-fat coded meaning of “flattering” is about hiding or covering up our bodies.  The way I use it now is about highlighting and celebrating our bodies.

Learning the ways my body differs from “standard” fit models for most clothing has been so helpful in dressing, both to highlight my features, and for comfort.  I’ve learned the following about my body: despite being average height (5’6”), I have a long torso and petite leg length.  I have a high waist.  My strap area (shoulders to chest) is shorter/more petite. I have thick thighs and a round belly that sticks out.  Understanding these things about my body helps me pick out clothes that are both more comfortable and more accentuating of my features.

Low-rise jeans were extra torture for me because my waist is much higher than your average fit intends.  This explains why, even with long shirts, I spent high school constantly tugging my jeans up and my shirt hem down to cover my belly.  That’s not comfortable for me.  It also explains why, when high rise jeans became popular, I still had the same problem and felt uncomfortable in them – a typical pair of high rise jeans on the market these days has a rise of about 11”.  Turns out I need a minimum 18” rise for a pair of pants to actually fit me like high rise jeans are intended to.  Fortunately, “Extra high rise” is now a thing.  I also get custom pants made from some of my favorite slow fashion brands, with an extra high rise built in.  Another trick I use is to buy tall fit pants even though I have short legs and get them hemmed, since tall pants are often made with a higher rise.

Because I have shorter legs, I find I like the look of cuffed pants or crop/ankle pants far more than I do full-length pants.  Its visually pleasing to me to see the shape of my ankles.  I’m also much more comfortable when I don’t have a lot of material swishing around my ankles.  Since my thighs are thick, when I wear short skirts or dresses, they look and feel even shorter on me than they are, to a level I find neither comfortable nor visually pleasing to me personally.  I only wear skirts and dresses at the midi length since that’s the most comfortable for me and a length I enjoy visually.

For tops, I learned that I do not like a v-neck neckline.  Due to my shorter shoulder-to-chest measurement, your average fit v-necks tend to show off much more of my cleavage than they would on someone with a longer shoulder-to-chest measurement.  I also feel that a v-neck visually shortens that area further in a way that makes me feel like I’m hunching in on myself, even when my shoulders are back and I’m standing tall.  Whether that’s in my head or not doesn’t matter.  What matters is that I feel like that’s the energy I’m projecting and since it’s not aligned with how I feel, I don’t enjoy wearing v-necks.

Understanding your body proportions helps make shopping simpler, especially if you embrace getting your clothing altered by a tailor or seamstress.  While this isn’t a valid option for every budget, it can be quite a problem-solver.  Alterations also don’t tend to cost as much as we might think.  Depending on the complexity of what you’re looking to have altered and cost of living in your area, many common alterations can be completed for about $15 per item.  I’ve had expensive slow fashion items altered and I’ve had super cheap fast fashion altered, all in the name of having a fit I like best. Instead of buying custom made clothing, tailoring a ready-made piece is usually significantly cheaper.

Have a small waist and wide hips, so every pair of pants you’ve ever tried has a gaping waistband?  Get them taken in at the waist so they fit everywhere.  Straps keep slipping off your shoulders because they are too long?  Get them shortened.  Yes, getting alterations done is an extra step, however, keep in mind that clothes in stores are typically made with one body type as a template and patterns for different sizes are graded up or down from that template, so off-the-rack clothes don’t really fit anybody, since no one perfectly matches that template.  Every woman I know and literally 100% of my clients have rightfully complained at some point that, “they just don’t make clothes for my body type.”  Get around this reality by buying clothes off-the-rack and having them altered to actually fit you well.

Comfort Must-Haves

If I am uncomfortable in something I’m wearing, I know without any doubt that people are picking up on my discomfort more than anything else about me.  More importantly, I’m not able to relax and enjoy or focus on whatever I’m doing if I’m distracted by my own discomfort.  Sometimes the discomfort I’ve felt in clothes winds up physically affecting how my body feels.  Sacrificing comfort for style is another fashion maxim I heard growing up and had to unlearn.  Prioritizing comfort has been a huge boost to developing my personal style!

Here are some things I’ve learned about clothes that do and do not work for my comfort needs:

Since childhood, I tend to get overheated easily and quite cranky when I’m too hot.  I often wear cardigans over tank tops, so I can take off layers if I start to get warm.  I also prefer to wear natural fibers like cotton, linen, and silk, since natural fibers breathe and don’t trap heat close to the body like polyester, nylon, and other synthetic fibers do.  Natural fibers also hold up better over time since they don’t trap odors.  This preference for natural fibers also makes shopping easier; I check what everything is made of and am very unlikely to buy anything synthetic.

I don’t like my wrists to be covered.  I can’t really explain why, but it makes me itch a bit to wear a long-sleeve shirt that covers my wrists.  I feel very constricted and generally agitated.  It’s a definite sensory no-no for me, so I don’t wear anything with long sleeves that can’t be rolled up.  My long sleeve items end an inch or two from my wrist.  I have a similar issue with half-sleeves, that end at the elbow.  I feel just as constricted, therefore I choose shirts that are either sleeveless, t-shirts, or ¾ length.

When I did my yoga teacher training, in addition to learning all about yoga, I learned that spending about 40 hours/week for 5 months wearing super tight yoga pants was not ok for me.  The constant compression on my abdomen was not just uncomfortable, it gave me painful gastric symptoms due to my organs being compressed all the time.  I would start my day in yoga pants feeling just fine, but by midafternoon, everything hurt.  Now I wear yoga pants only when I work out.  A few hours a week versus 12 hour stretches multiple days a week makes that possible.  But it means I also avoid incredibly tight regular pants.  I used to suffer through all kinds of cute, trendy pants that I like to call “standing pants”; they fit great and comfortably enough when you’re standing up, but the second you sit down you need to pop your button and let the zipper down a bit.  No more!  Life is too short to be miserable when you’re sitting down because of your stupid pants.

Turtlenecks, choker necklaces, high neck sports bras, high boat necks, halter tops/dresses – all of these are strictly forbidden in my wardrobe.  I cannot stand anything squeezing my neck.  It’s an incredibly uncomfortable sensation for me.  When I’ve tried wearing any of those items in the past, I immediately notice I’m tugging at the collar, trying to find more room.  Again, I don’t want to project the energy of discomfort, but simply put, when you’re constantly tugging at your clothes, that doesn’t communicate style.

Refusing to sacrifice comfort makes my style decisions that much easier, decreasing the burden on my brain to make things work that I don’t enjoy. It helps me make decisions and have greater consistency in my wardrobe, creating the feeling of consistent style.  

The Process

Developing your personal style doesn’t happen overnight.  It takes time to notice many of the preferences I describe here.  KonMari-ing my wardrobe was a huge help for making me aware of what I actually preferred when it came to clothing.  My closet was full of stuff I had spent years trying to make work, that I felt guilty about spending money on and not wearing, or that made me feel less-than because I couldn’t figure out how to get that specific look right.  I had so many items in colors I knew I hated wearing, purely because someone else told me they looked good on me.  There were dresses that looked cool, but pinched my shoulders so much they hurt at the end of the day.  By pulling everything out of my closet and only putting back in the items I knew I loved, I saw very clear patterns to what I liked and what I didn’t.

Do your best to give yourself free rein to explore and experiment.  Take notes in your phone of what you find yourself gravitating towards and away from.  Refer to those notes when you’re shopping.  Follow fashion influencers that look like you or have a similar body type.  Slow your brain down by taking three deep breaths every time you try on a new outfit then ask yourself how you really feel about it.  Play around with styles you would normally never gravitate towards to see if they might actually please you.  If your body type allows you to shop in person, dressing rooms are your best friend for experimenting without spending money.  If you’re in a body like mine that forces you to mainly shop online to experiment, I feel your frustration and encourage you to double-check the return policy.  If your budget allows, order multiple sizes of something you’re hoping to try.

 But most of all, listen to yourself! Let your unique preferences and creativity out. The world wants to see what you can do, personal fashion sense very much included. You hold that knowledge in your heart if you take the time to hear it. Listening to yourself has a huge ripple effect in life far beyond self-expression. It’s the root for making any intentional strides in life and for creating a life that suits you.