Stop following archaic conventions:
You don’t have to “match” everything, just make sure everything “goes” together.
Brown and black are neutral, therefore they may go together.
Belt and shoes don’t need to match.
You can mix patterns, such as stripes and plaids, but that’s more of an art form than a science.
Stop using the term “matching.” Buy clothes that you think fit, and even then you will probably need to tailor it. In any case, find a a good tailor and build a relationship, you never know when you will need an emergency hem. Successful layering—- 3 or more layers.
Examples: button-up shirt, tie, vest, jeans.
Button-up, tie, cardigan/sweater/jacket, jeans.
Button-up (no tie, buttoned up to second or third button from top), v-neck undershirt, vest, blazer, jeans.
Notice I’ve included jeans but bottoms are not considered a layer, just wanted to point out that you can wear ties and such with your, hopefully dark, jeans.
WARNING: layering like this will make you look very put-together; you will be noticed. Shoes. Again, mix it up. Wear some sneakers with your suit, or just the suit pants (and then a t-shirt and leather jacket). Wear dressier shoes with a more casual outfit (like chino joggers). Just buy good shoes (leather upper and lining) because those $50 shoes will last you two months. Accessorize, but don’t overdo it. Guys are particularly afraid of this area. If you don’t have a watch, go buy one. Think simple and classic, try to avoid the oversized watches.
Usually you want an everyday watch like a gold one with a metal band and a dressier one with a leather strap. Most importantly, don’t take yourself so seriously. Have fun with it, and stop listening to people like me. If you find that your signature style includes that oversized watch, then you do you. As a side note, I didn’t include specific styles because trends always change. Even if you believe so or not, you conform to this by buying what’s out there. Everyone’s into minimalism and basics and joggers right now but that might not be the case in a couple years. Keep up to date with fashion but it’s not the Bible, developing your personal style first will let you incorporate them as they come instead of living by them.