Not sure this is in any particularly order. Just some guidelines, if you will:
Stick to one 'loud' piece per outfit. That almost always should mean a pair of sneakers, or a scarf. Not a polkadot pair of jeans.
Before you commence experimenting, buy and own some good, solid pieces. You need some classic, everyday kicks before you need those Jeremy Scott Adidas with the bear ears.
Flip through a men and women's fashion magazine every now and then. Every couple months is fine. Do it while you're taking a shit if that makes you feel more like a man. What'll begin to happen is you'll start to refine your eye. You'll retain the information and make better decisions when getting dressed without even noticing you're any different of a dude.
Not everything that 'works', works for you. Also, a lot of those things that work, only work when paired with other pieces you may not own or can't pull off anyway with your gumby ass.
Don't wear sunglasses at night and/or in the dark unless your net worth is over 50 million.
If you find something you really like and see yourself getting a lot of use out of, buy two of them.
Own a good denim button-down shirt.
Generally stick to a 3-color rule from ankle to neck. I say ankle to neck because this rule should not include footwear or hats.
Invest in a watch made by a company that makes watches. Levi's makes jeans. Don't buy a Levi's watch.
Forget about trying to match. Find color schemes that work and you enjoy.
Buy a good pair of jeans. Good meaning well-made denim. Don't wash them for a long time (like a year), and when you do, be prepared to then buy another pair. If you're a regular person, don't worry about getting them dirty. Just shower daily and wear them like a human being and you should be fine.
Fuck trends. Stick to classic. Think about the type of stuff that's never gone out of style. Blue jeans, wheat boots, white tees, brown belts, black jackets.
Know your size. Nothing looks worse than someone who's a 2X trying to fit into a medium. Just own being a 2X. Your legs have committed, you should too. Big people can look absolutely great in clothing that fits right. Or they can look fucking terrible.
Care. It's one thing if you're reading this and you're on a farm somewhere squeezing milk out a teet, but if you're a human trying to make something of your life, the way you're dressed is going to directly affect how people perceive you and your work. Sorry, that's the way it is.
You know how they say to never order seafood from a diner? Yeah, don't buy a suit from H&M.
If you're dressed casually, wear your pants a little lower than you normally would. If you're in a suit, pull them shits up as high as possible.
Never roll up the sleeves on a sweatshirt. Luxuries such as these should only be reserved for button-ups.
Iron stuff. Wrinkled and shitty excudes your life is out of order.
For God sakes, dry clean the good stuff.
Shop sales. There's no good reason not to. Everything goes on sale in this world except Apple products.
Essentials: (If you can't afford them all at once, do what you can.)
a 100% cashmere black crew neck
a brown leather belt
one pair of dark raw denim jeans
one pair of light distressed denim jeans
a cream waffle-knit thermal
a pair of boots
2 pairs of gently-worn sneakers to rotate between
a bright, solid color beanie
multiple white and black tees
Dope shit you don't need but should want:
100% cashmere sweatpants
a $1,000 plus watch, something you can pass on to your kid
things from Bergdoff
a black card
yearly vacations with lovers and/or friends
multiple suits, sport coats
Love you guys, Happy Holidays.