I'm quite as challenged and have the giveaway bags to prove it. But like you, Mochi, I think I've gotten a little better.
Practice really IS key. And the advice to 'play' in your closet is spot on. Yes it is a large investment of time, and can be chaotic --- but helps immensely in the long run. I realized that when I got fed up of digging through seasonal storage (and the repacking!) every time work sprung on me a little-or-no-notice trip to a very different climate. Eventually, I figured it made more sense to invest the time in making up 3-4 sets of capsule wardrobes for various weathers, cultural fits and registers of formality. It took DAYS, and messy days at that, of pulling everything out and putting everything together EVERY which way I could.
Wasn't easy to make it work for northern Europe or West Asia using pieces from my largely wet-and-warm tropical wardrobe. Some of the combinations were just outright mad (or so I thought at the outset), yet still worked when I actually put them on. I resorted to photographs and flowcharts to keep track. The result, though, was a single suitcase of versatile, compact clothes that I can just add a few accessories and basics to, and I can take a trip on a day's notice.
The unintended result was that I became a little more experimental in putting together everyday items too. Experimenting develops that 'what if...?' muscle in the imagination a bit further, I find.
And you can of course feed that same muscle with a lot of browsing, from magazines to pinterest, plus what so many members on this forum seem to share with each other. So, thank you, ladies! been lurking a while, and this seems like a good time to acknowledge how much of a help it has been to watch you wear your wardrobes!
Another strategy I found especially helpful is to figure out (that's where flowcharts, photos, spreadsheets REALLY help) what colours I wear best, what colours I most gravitate to, what shapes of necklines or lengths of sleeve are most versatile. For myself, I found dark neutrals the most useful for travelling and repeating. I found I look to jewel colours and darker brights for the feel-good factor. I found knits lose or resist or hide their wrinkles better than wovens, and conversely heavier-weight wovens (jeans, jackets) best for adding no-iron, tailored structure. I found I wanted sturdy, supportive walking shoes with a bit of heel for travelling by day, but ones that slip on and off easily (for plane trips, temples etc), plus very compact, lightweight, slip-on evening shoes. I found a three-quarter or longer sleeve is more versatile for layering as shorter sleeves bunch up under the next layer; or else go sleeveless. Similarly looser or adjustable waists are easier to layer than absolutely fitted. I found longer-length tops (like tunics) more versatile across cultures and climates. I found I didn't want to fuss with too many ties and zips that can get caught and broken on the go. Similarly, I found longer/larger scarves are easier to wear different ways.
Why the long list? To show you how I found the elements to look for when I go shopping. Colour: Dark neutrals or darker brights; plus the occasional primary or neon bright for pop. Shoes: Sturdy, chunky-heeled day shoes for walking; lightweight and flatter for evening. Fabric: Either wrinkle-resisting (knits), or wrinkle-disguising (denim, corduroy), or wrinkle-flaunting (linen, 'crushed' cottons and silks); no dry-clean-only. And so on --- you get the picture. I too have the tendency to see 'pretty fabric' or 'nice texture' when staring at hangers; but now I look harder to see how the neck and sleeve are cut, length, etc. Of course WHAT you end up with as 'to look for to suit me' will depend on your specific lifestyle --- but I found, quite by accident as you see, that HOW & WHERE will I wear most of clothes a good way to sort out what works the best and the most for me. Your particular parameters of practicality should give you your individual cues too.
Of course, I've equated 'versatility' (which you asked about) with 'practicality' for my purpose. But I do think they are close allies. Easy to wear many ways, comfy and easy to care for are common across both categories, right?
Sorry to have been so long-winded! Didn't know how to explain the thought process clearly without examples. Hope that made sense!