Where Are You? The Stages of Learning About Fashion
- Stuart
- Jul 19
- 10 min read
Updated: Jul 30
Learning about fashion and styling is similar to any other creative hobby. You might see someone do something cool in the classroom or at work, and you want to emulate that. Maybe your algorithm sent you a GRWM, and something about how they put things together spoke to you. For me, it was movies and figuring out how to emulate the spirit of my favorite characters in my wardrobe.
But learning style is not a one-and-done process, no matter what the books might tell you. Like learning how to paint or roller skate, you can spend the rest of your life learning about fashion and style, and there will still be more to learn.
Luckily, you don't need to know everything to have great style. I don't know everything about origami, but I know just enough to make a cool little dollar bow-tie. You can take your fashion knowledge as far as you want. If that's just enough to know how to dress for the office, then you're gonna be okay.
But in order to grow, you need to know where you're starting. I've created a guide that can act as a map on your style journey, along with tips to help you get to the next phase of learning about fashion.
The Total Novice: The First Step to Learn About Fashion
Welcome to the beginning of your journey! If you're a total novice, there's a chance you wear a lot of graphic t-shirts and jeans combinations. You know your clothing size, maybe a few colors that you like (although you always end up wearing black), and that is it.
And that's okay! There's so much you can build on with just those two pieces of information. Yeah, it's not exactly the sexy or cool kind of info. But knowing your size and preferred colors is the foundation that will allow you to take more style risks.
Let's start with size: I'm sure you've noticed that a size L at Target is not the same as a size L on that random TikTok store. I've had very frustrating experiences where I'd order "my usual size" only to find out it's too big or too small, and always unflattering. The best way to get around this problem is to learn your measurements. If I could descend from the sky and gift you with one tool, it would be a cloth measuring tape.
The second thing we'll start with is colors. You might have heard of The Color-Me-Beautiful system, where everyone has a "color season" that fits best with their skin tone and hair color. If that's something you want to explore, then go for it. But because the information can not only be overwhelming (and you might not even like the color season they give you), here's what I'd suggest instead.
If you can, find your way to a store like Old Navy, a department store, or an online place like Land's End. Make sure you're well-rested and well-fed, and bring a hype-friend if you don't want to go alone. Look for the plain t-shirt section, and pick out a bunch of t-shirts in a variety of different colors (no black, please, we're trying to expand our horizons). Go try on the different shirts, taking pictures as you go, and see what colors you like best. It's really that simple.
Knowing your measurements and which colors you like will give you the mental foundation you need to expand your style and start the exploration part of your style journey.
Where do you start exploring? Anywhere! Pinterest and TikTok are useful tools to find new styles. Look for patterns in what you've saved, like the kind of silhouettes, colors, fabrics, and overall vibes you're going for.
I also get inspiration from movies, magazine ads, comic books, and even art pieces. Some people find inspiration on the runway, but I'll admit that runway shows are intimidating for most people. When you're looking at a runway show, you're often not looking at pieces that you'll find on the shelves. Rather, the designer is using fashion to create something like modern art. If you're an art kid who's used to that, then go for it, but if you're a normie like the rest of us, I'd hold off on runway shows for a while.
Resources for The Total Newbie
The Style Enthusiast
Right, so you know your measurements and the colors you like wearing the most. That's brilliant! But what else do you know?
Amateur Fashioners probably know at least two or three things from the list below:
Size and "Body Type"
Clothing Silhouettes (e.g. A-Line Skirt and "Cigarette" Pants)
A Handful of Basic Color Combinations That They Enjoy
Their Favorite Style Aesthetic or Energy
Let's tackle these things one by one.
Size and "Body Type"
An Amateur Fashioner knows their size measurements (using their handy cloth measuring tape) as well as their body type. You can see the body types in the image below, but the most common ones are
Hourglass
Triangle (Pear)
Inverted-Triangle (Apple)
Rectangle
Each body type is determined by the natural way your body puts and distributes weight as you get older. This is by no means a scientific study, but it's a good thing to know when you're learning what general types of clothing and accessories work best for you.
With that said, many rules around dressing body types focus on hiding your flaws or making you look smaller. I prefer the rule of dressing your strengths. It takes the same rules about body types, but uses them to emphasize the things you like about your body. It trains you to view yourself in a new way, which is only going to help your self-confidence and style.
Clothing Silhouettes
There are dozens of ways to classify the shapes of the clothes we wear. You may have heard something like "V-Neck Slim Cut Short Sleeve Shirt," which is different from a "Crew Neck Relaxed Fit Cap Sleeve Shirt."
If you understood all that, you're probably well-versed in Clothing Silhouettes. You can confidently navigate your way around an online store without ordering something too weird. If all that sounded like gibberish to you, don't worry. All you need to do is find a few of the styles you like best and learn those names. You can find more information here, on the Hero Looks Pinterest account.
Color Combinations
You've moved beyond knowing your favorite colors to wear into the full-on color wheel. You know the difference between primary colors, secondary colors, and what kind of colors complement each other. You might even know about warm tones, cool tones, and other hues. More importantly, you know how to mix them in your wardrobe for maximum effect!
I have an entire post about choosing the right colors for you, plus everything you need to know about the Color Season system. You can check it out here!
Aesthetics and Energy
Finally, the fun part of your fashion journey!
Aesthetics, or "scenes" as the older folks called it, are a tried and true gateway into caring about fashion. The aesthetic can be anything: punk, dark academia, cottagecore, clowncore, royalcore, the lists go on and on and on. Whether you saw it in a movie, online, or a random episode of RuPaul's Drag Race, an aesthetic will attract you, invite you to explore, and maybe even inspire you to imitate! It's that "je n'sais quoi" of your fashion adventure that makes it personal.
With that said, within each aesthetic comes a sub-classification, and this is where it's easy for you to get lost. That's because aesthetics with staying power (a hashtag that lasts beyond a month, for example) will also develop its own subculture. Ask any fan of the aesthetic, and you'll soon discover there are multiple different ways to embody the look. There may be some contention about which way is the right way.
This is where my 12 Archetypes system comes in. Think of your favorite aesthetic as a genre, like Sci-Fi or Fantasy, and your archetype as the character you play within that genre. It'll give you a more personalized path for your fashion journey.
Once you find that overlap between your Aesthetic and your archetype, you can find a few brands you like and stick with them.
Resources for The Amateur Fashioner
The Fashion Majesty
You're finally at a point in your style journey when this all should start feeling easy, right? You know your body type, your most flattering silhouettes, and your preferred aesthetics. You have brands you like, and you're always the most fashionable one at any party.
You also have a surer sense of yourself. Maybe you've gone through some things, or rediscovered parts of yourself that feel good, comfortable. Maybe you've aged and now have a new perspective on the culture around you, including how your style interacts with it.
So why does this all still feel so difficult?
I've got two words for you, Fashion Majesty:
Information Overload.
We're living in a time when you can find any style you want. You can learn every accessorizing trick in the book and discover every dirty secret about the fashion industry. You don't even have to look for stuff, it'll just find you via the algorithm.
Sometimes, that's brilliant! I've gotten so many cute accessories from Etsy that I never would have known about if it weren't for the algorithm. And yet it also feels invasive.
Social media companies will send you whatever they can to keep you using their platforms. In between the interesting tidbits of history and the subculture deep dives, they send you ads. In fact, did you know that on average, you see about 1,000 ads a day? That's a lot of marketing designed to mess with your basic human psychology!
So yes, deciding what to wear can feel like a lot. But never fear, Fashion Majesty, we have a plan to help you navigate this part of your journey.
But if you're here, then you won't find the answers in another How-to-Dress guide. It's time to look within yourself if you want to keep going. I will ask you questions, and I encourage you to journal your answers. Not all the answers will immediately spring to mind, but if you let them rattle around in your brain for a bit, the solutions will come from the most unexpected places.
If you want more details to help you answer these questions, you can check out this post here.
1) Look to Your Past Self- What were you wearing? How did it make you feel? Was there a time in your life when you felt creative, free, and excited? Do you remember what you were wearing?
I'm asking you these questions not because I think you should recreate the exact thing you used to wear. If you want to, go for it, but keep in mind what served you then might not serve you now. The real reason I ask this question is that we have to go beyond the superficial "buy guide" and into what works for you. The answers to this question can range from "my wedding outfit" to "a pair of pajamas at an all-nighter with my friends," and you can't exactly wear those to your job.
2) What Are Your Current Values? What are the Things that Excite You Most? How Can You Incorporate That into How You Dress?
In certain fashion circles, this question elicits knee-jerk virtue signaling answers. There are some people who say "I value the environment," and by god, they mean it. There are others who say the same thing... right up until it's inconvenient. But it's an important question, because at some point in your fashion journey, you have to realize that none of this matters if it doesn't matter to you.
So I want you to answer this question truthfully and thoughtfully. No one's going to know the answer except for you.
3) What Do You Need Right Now? Have you gone through a big life change? Has your body changed? Has your environment changed? How do these things need to impact your wardrobe?
This is one of those questions where the answer might immediately spring to mind (e.g., you're going back to the office after years of WFH). Write down whatever you thought of, but then I'd encourage you to keep this question in mind over the next few days. Make a note of whatever comes up, and write it down with the first part of your list.
4) How Do You Behave in Your Clothing Now? How Do You Want To Behave in Your Clothing?
This answer will be a mix of all three previous answers. As much as we need to look inward, at some point, you have to live in the real world. So, with all three previous answers at your fingertips, how do you want to behave in your new refined style?
Answering these questions will not immediately solve your fashion woes, but you're experienced enough to know that this takes time.
Resources for the Fashion Majesty
The Fashion Master
I imagine you're thinking I'll make a joke about "You don't need to be here! You know it all! You're the master!" You're at the point in your fashion journey where you know pretty much everything you need to. You're comfortable in your own skin, your own clothes, and your own taste.
So why are you here?
Because it's fun.
Honestly, that's it. You like learning about these things, and you enjoy adding new thoughts and ideas to your worldview.
That's the thing about The Master, in fashion or otherwise. Masters know that the true masters never stop learning. They're always open to sharing and receiving ideas, because when you truly love something, why would you want it to end? A true Master loops back around and approaches their world through the novice's lens. You know, you may be a master at mixing patterns or finding the best piece for your collection, but there's always something you can improve on.
My best advice for a Fashion Master who is stuck is to stop looking at fashion and start looking at the world. Go back to the things you love, maybe even the things you were passionate about as a kid. Was it a hobby, a movie, or a video game? Were you inspired by a character or a band? Or do you find yourself drawn to something new?
Give your fashion brain a break, and go all in on that thing you love. You'll find your way back to your style, but it'll be with a fresh new perspective.
Resources for the Fashion Master
Art Galleries and Science Museums
Final Thoughts
Wherever you are on your fashion journey, it's important to know that you're not alone. Everyone is just trying to figure things out, and figuring out how to dress is just one of the many ways to do it.
There's been lots of resources throughout this post, but if you need anything else don't hesitate to reach out! I'd love to hear from you!
As always, stay curious and stay hydrated!
This post contains affiliate links, which means I may receive a commission if you make a purchase through my links. I only recommend products I believe in and that I think will be helpful to my readers.
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