Maybe it’s part of your job where you’re incredibly well-versed. Maybe it’s a hobby like cooking or crafting. Or maybe it’s something that comes naturally to you, like math, art, or learning languages. Whatever it is, you’re so skilled at it that it feels like second nature. You don’t have to think about how you do it. You just do.

Now imagine being asked to teach that skill to someone else.

Train a new hire. Walk someone through your hobby. Tutor someone who’s struggling. If you’ve ever been in that position, you know how surprisingly difficult it can be, not because the other person can’t learn, but because you have to slow yourself down enough to explain something you no longer consciously think about. You have to rewind your own expertise and meet them where they are.

This happens to me with clients all the time.

I can look at a single piece of clothing and immediately see multiple outfit combinations, what feels obvious, intuitive, and almost automatic. And then I’m reminded that for the person I’m working with, it’s not obvious at all.

That’s not a judgment on them. If anything, it’s a blind spot on my part. It’s easy to forget that the skills I take for granted aren’t widely understood, and I can certainly name plenty of areas where I am completely out of my depth.  You can read more about this here.

A client explained it to me this way, “My challenge is being able to identify the pieces and then put them together. It’s very black and white to me—when really, it’s all shades of gray. When I see an outfit, my brain wants to replicate it exactly. It can’t color outside the lines.”

And that’s exactly it.

When you don’t have the underlying skill set, getting dressed feels like an exercise in getting it “right.” So you look for rules. You look for formulas. You look for something you can copy exactly.

But style isn’t a fixed set of instructions; it’s not black and white. It’s built in the gray through small decisions like adjusting a proportion, changing a shoe, or adding a layer until the whole thing clicks.

If this is how your brain works when you get dressed, there’s nothing wrong with you. You’re not lacking taste. You just haven’t been taught the process.

GIVE YOURSELF SOME GRACE

I am a knitter. The first project I ever made was a ribbed scarf for my husband. While he cherishes it as one of the best gifts he’s received, it is hardly the most difficult project I’ve ever taken on.  At the time, though, it was.  Since that first scarf, I’ve become a pretty adept knitter. I can take on projects now that I couldn’t have even fathomed when I was starting out.

We all have to start somewhere. We don’t become advanced at something without first being beginners. It’s the whole crawl before you walk analogy. If I had started with a cable-knit sweater, I would have floundered, gotten frustrated, and probably given up. It was starting small that allowed me to build my skills over time. My point is, putting outfits together is a skill. Like any skill, it takes time to develop. And if it doesn’t come naturally to you, it’s not something you’re going to master overnight.

Most people don’t give themselves that grace. They expect to open their closet and just know. And when they don’t, they assume something is wrong with them.  There isn’t. You’re learning how to see things you haven’t been trained to see yet. Proportion. Balance. How pieces interact with each other. That takes practice.  So instead of trying to get it “right,” start smaller. Start by getting it a little closer.

ACCEPT WHAT YOU’RE WILLING TO DO

I have a client who has openly admitted that she will always struggle with putting outfits together. In her words, her brain just doesn’t work that way. Do I believe she’s completely incapable of developing this skill? No. She’s smart, capable, and well-educated. If she chose to invest the time and energy, she could absolutely improve. Just like I can knit a cable-knit sweater now, even though I started with a simple scarf.  

That said, do I think she’s ever going to become masterful at creating a look? Probably not.  Not because she can’t, but because she doesn’t want to spend the time and energy it takes to get there.  And that’s a completely valid choice. We make these decisions all the time. There are things we choose to learn deeply, and things we’re perfectly happy letting someone else handle. Getting dressed can be one of those things. And given how much else we’re managing in our lives, that’s a reasonable decision.

Where it becomes a problem is when what we expect to achieve isn’t aligned with what we’re willing to do to get there.  In my client’s case, that clarity is exactly why she hired me. It’s also why she’ll likely always be my client.  Nothing is disempowering about that. If anything, it’s incredibly self-aware.

SIMPLIFY

If putting outfits together feels difficult, that’s usually a sign you’re trying to do too much at once. When you struggle to build looks, complexity works against you. The more variables you introduce, the harder it becomes to see what’s actually working and what isn’t.

So simplify.

Start with pieces you know are easy. Combinations you’ve worn before. Outfits that feel at least mostly right.  Then build from there. Instead of trying to create something new every time you get dressed, work with what you already know works and make small adjustments. Change a shoe. Add a layer. Tweak a proportion.

You don’t need to reinvent your wardrobe. You need to make it easier to work with in a way that matches your current skill set.

LET YOURSELF OFF THE HOOK

There’s also something else worth saying here.  Women are often expected to just know how to do this.

Somewhere along the way, the message became that getting dressed well is something you should instinctively understand. That you should be able to walk into your closet, pull things together, and look polished without much thought.  And if you can’t, it must mean you’re not just doing something wrong, that you are wrong in some way.  But that expectation doesn’t make much sense.

Let’s also talk about how people in fashion have been portrayed in the media, or in television shows and movies.  How many times has the dumb girl been portrayed as someone who couldn’t get into college and wound up in a fashion-related job?  These characters are usually portrayed as shallow, vapid, unserious, and not that bright.  It’s easy to assume that any idiot could go into fashion.

Look, I’m not pretending to be a MENSA candidate, or that most of my clients aren’t heaps more impressive than I, because I do have pretty impressive women as clients.  However, my point is, if how people in fashion are often portrayed as dumb dumbs, then it would reason that we’d feel pretty silly for struggling with putting one outfit together.  

It’s not about being smart or dumb; it’s about possessing different skill sets.  My very bright, very accomplished clients come to me with tremendous respect for what I can do because they realize that, for as smart as they are, this is something they just can’t do.  They let themselves off the hook.  

Most of us were never actually taught how to put outfits together. We weren’t taught how to think about proportion, how to combine colors, or how to evaluate whether something is working or not. We were just expected to figure it out. So if this doesn’t come naturally to you, it’s not a personal failing. It’s a lack of instruction.  And once you understand that, it becomes a lot easier to approach getting dressed as something you can learn, instead of something you’re supposed to already know.

WHEN INSTINCT DOESN’T WORK, START WITH FORMULAS

Said the person who earlier said that formulas aren’t the answer, but hear me out.

I have always styled by instinct. For clients who struggle, instinct isn’t something they can rely on, and it’s certainly not something I can teach.  But that doesn’t mean these skills can’t be developed. While it may never feel instinctive, it can absolutely improve.

A few years ago, I went back through photos from styling sessions with my clients to see if there were consistent patterns in how I was putting outfits together. I wanted to know if there was a way to translate what I do intuitively into something more concrete. That process led me to develop several styling formulas (read here), which I’ve also written about in more detail, including Focal Point Styling, Road Map Styling, Harmony Styling, and Complementary Styling.

For someone who struggles and wants to get better, these can offer helpful places to start.

But here’s the important part.  Formulas are guideposts. They are not gospel.  Think of it like cooking. You can follow a recipe exactly, or you can improvise. And how much you improvise usually depends on how comfortable you are.  Or, as I’ve written about before, you can learn the rules well enough that you can stop thinking about them and just wail.

STYLING IS A SKILL

Getting dressed isn’t about having a natural gift or some elusive sense of style that you either have or you don’t.

It’s a skill, and like any skill, it can be learned, improved, simplified, or outsourced, depending on what you want and how much time and energy you’re willing to put into it.  If it doesn’t come naturally to you, that doesn’t mean something is wrong. It just means you haven’t built the skill yet.

You can start small.
You can simplify.
You can use structure when you need it.
You can get a little closer each time.

Or you can decide that this isn’t something you want to spend your time figuring out on your own.  All of those are valid choices.

But what doesn’t work is expecting ease without building the skill, or expecting mastery without putting in the time.  Once you understand that, everything about getting dressed becomes a lot less frustrating and a lot more manageable.

And if you want help fast-tracking that process, that’s where I come in.  It’s the perfect time of year to schedule a complimentary Image & Style Assessment with me.  Click here for more.