[Scorpio]

Besides reading up on the basic fashion rules and guidelines online, what worked for me was to find a store where I liked the clothes, and I liked the sales people, and then I just deferred to their expertise and asked them to help me pick out outfits. The key is finding a place where you get a sense the staff won't dress you up in something unflattering just for a commission.

Another guideline is to just try lots of things on until you develop an instinct for what looks good on you. Clothes that look iffy on a hanger may look pretty good on your body.

One more thing is to not fully trust your comfort zone. Even if something looks good on you, if it pushes your previous boundaries, you'll feel vaguely uneasy. I mean this is terms of how the clothes physically look, but also baggage you may have towards certain styles or pieces of clothing (e.g., "I can't wear a suit, that's so corporate!") If you ignore that feeling, you can get used to wearing better-looking, but slightly boundary pushing outfits.

Finally, shopping drains you at first if you don't like it, but you can build up a tolerance for it over time. Eventually picking out a nice new shirt that flatters your appearance can be rewarding.