I think being able to dress yourself is about two things: developing an eye for proportions and shapes and necklines and colours and fabrics, and deciding what you like, enjoy and feel comfortable in.
So what do you like? What colours or fabrics or shapes or silhouettes appeal to you? What textures do you enjoy? When you look at fashion blogs or Pinterest or Instagram, what catches your eye? When do you say, “ooh, that’s nice”?
If you’re not looking at fashion on the internet, do it. Just browse and see what you like, what shapes appeal, what outfits you enjoy. If you were learning art history, looking at paintings would be part of your study, if you want to dress well, (as opposed to just covering yourself up, which is ok too), it’s a matter of educating your eye.
Treat your body like a room you are decorating, you want colours and patterns which blend well, furniture which suits the shape of the room, decorations which make sense for the people who will use the room. If you have great windows, you don’t put a cupboard over them, but you might put a table in front of the bit of chipped paint in the corner.
See if you can find people with a similar shape - look up “apple body type”, and see if that helps you. Just look at the pictures and imagine yourself in the outfits. Do you own similar pieces that you could experiment with?
I find Trinny’s makeovers on YouTube interesting because she’s good at pushing people to wear things out of their comfort zone. I don’t always like the result, but she’s good at granular descriptions of why things work. Her wardrobe series on Instagram does the same thing - it’s not about looking like her, but seeing how she puts things together.
Justine Leconte, also on YouTube is really good at explaining how different styles work for different shapes.
After a while you’ll probably find some shapes and styles keep reappearing as things you like, so take note and then go to a store and look for those shapes and colours and try them on. Do you feel happy and comfortable? Do you think your good features are emphasised? Does the colour make your eyes sparkle? Can you move around easily in them? Do they work for your lifestyle?
Building your style is about expressing yourself through clothes you like and are comfortable wearing. And I mean comfortable as in relaxed and not constantly tugging at your hemline or crossing your arms over your cleavage because you’re not enjoying your clothes. Even formal and fancy clothes should fit you properly and not pinch, gape or ride-up. Liking your clothes and feeling comfortable in them gives you confidence, which is most of the way to being stylish.
Ask someone who loves you what your best features are - you sound very hard on yourself and I suspect what you see and what other people see, are quite different. A friend with a good eye can be a great help - if you know such a person, take them shopping or go through your wardrobe together.
Don’t worry about fashion, once you know what works, you can fold fashionable stuff into your wardrobe if that’s what you want to do. In fact a lot of the usual fashion advice is not helpful - a white shirt does not suit everyone; wrap dresses rarely fit well enough to justify the annoyance and the “French tuck”, makes most people look half-dressed.
I buy most of my clothes at charity shops nowadays, because I can find better quality items than I can afford new. They are also an excellent way to experiment with shapes and colours; if you make a mistake, you’re not much out of pocket and you can donate it
Also, well-fitting undies can make a real difference to how your clothes fit and feel on you and a good, easily managed haircut will help make you look stylish whatever you’re wearing.
Here’s some inspiration.
www.thesartorialist.com
www.advanced.style