When you first start trying to style yourself, it can feel a bit odd, a bit slippery. You have one outfit that has a lot of the same things as another outfit and one of them feels peaceful, easy, and right and the other feels a bit wrong, but it’s hard to tell why. It’s normal. You develop a good eye for style not by buying more clothes or trying to make drastic changes, but by looking, tinkering, and comparing. The first thing you need to do is stop asking yourself, “Do I like this?” and start asking yourself, “What is this doing?” A jacket is adding some structure.
A soft fabric is making this feel easy. A contrast is stealing too much attention. When you can start naming what each item is doing, you can start studying styling. One way to do that is to work within one outfit and change one thing at a time. Put together an outfit from the clothes you know you wear and then swap out a shoe or a top layer or a bag. Get in front of a mirror and see what changes. Does the line feel cleaner or busier? Does the color story feel more peaceful or choppy? That will teach you more about style than throwing together 5 outfits as fast as you can. It will teach you to pay attention to line and proportion and emphasis. Don’t make the changes so big that you can’t see the difference. When you change everything all at once, you can’t tell what made the outfit better and what made it worse.
One thing that often happens when you’re just starting to try to style yourself is that you’ll throw a lot of interesting details into an outfit and it will end up feeling messy instead of intriguing. You’ll throw a textured knit with bold earrings with a patterned scarf with volume trousers with statement shoes and each item will be great, but together they will be too much. When that happens, the fix isn’t to remove the interesting details. The fix is to let one thing take the emphasis and then use everything else to support that thing. If the trousers are full, then make the top simple. If the earrings are bold, then simplify the neckline. When an outfit starts to feel good, it’s because the different items feel related instead of competing with each other.
If you only have 15 minutes to practice, that’s okay. It’s better to have a contained practice than to throw a bunch of clothes around like a mad person. The first part of your practice should be deciding what you want to focus on. Maybe you want to think about contrast. Maybe you want to play with layers. Maybe you want to pay attention to the fit through the waist and shoulders. The next part of your practice should be building 2 versions of the same outfit with whatever you’ve decided to focus on in mind. Then the last part of your practice should be taking a picture of the outfits and looking at them later instead of trying to evaluate them in the mirror. Looking at an outfit in a picture will slow down your reaction and will help you see things you can’t see when the outfit is moving.
You’ll be able to see where a hem cuts the leg line or where a sleeve changes the balance of the upper body. If you do this a few times a week, you’ll start to see patterns. You’ll see which combinations always tend to feel peaceful and which combinations always seem to clash. If you get stuck on an outfit and feel like nothing is working, it’s probably because every outfit you put together feels either too boring or too try-hard. Instead of trying to totally overhaul your style in one afternoon, pick one thing you want to focus on and study it for a few days. Maybe you want to think about jackets. Maybe you want to think about neutrals. Maybe you want to think about different ways to style a pair of trousers. And don’t worry if you keep repeating the same things. That isn’t a lack of imagination.
That’s just developing your taste. You’ll start to see that the difference between a length that’s a little bit cropped and a length that’s too short is pretty subtle. You’ll see that the difference between a relaxed fit and a shapeless fit is pretty subtle. You’ll see that the difference between a soft contrast and a flat contrast is pretty subtle. But you won’t see any of that if you’re jumping around between a million disconnected ideas. The best kind of feedback you can get on your outfits is specific. Instead of asking if the outfit looks good, ask what the first thing is that you see or if the proportions feel even or if there’s anything that interrupts the line of the body. Any feedback that you get should point to something you can see, not something you can only feel.
Then try that feedback on for size. If someone tells you that the outfit feels heavy on top, try changing the top or adjusting the way the top fits and see if that makes the outfit feel better. All of this is eventually meant to help you learn to trust your own taste. When you get into the habit of regularly practicing your style, when you get into the habit of slowly and carefully evaluating your outfits and making specific changes, you’ll get better at styling. You’ll trust yourself more and more to see when something works and to know how to fix it when it doesn’t.