Originally Posted by mafoofan
That is certainly the popular opinion here, but you will find that many of the better informed members would strongly disagree. Sorry Spoo--you seem like a nice guy, but you dress poorly, and it doesn't have to be that way.
Think less about finding "combos." We are not women. We don't buy outfits. We build wardrobes. Buy staples that can be easily paired. Learn to do that by picking up "rules" and learning what is classic. You will naturally develop your own taste and eccentricities over time without trying to grow a personality.
For fall/winter trousers: buy many, many pairs in light or medium grey. Flannel or twill are very versatile. The former arguably looks and feels better, but the latter is harder wearing and perhaps easier to take care of. You can wear grey trousers with pretty much any jacket without having to think hard about it.
For jackets, concentrate on simple, staple patterns with brown and tan backgrounds. Preferably, these jackets should be in rough, textured cloth appropriate for odd jackets. Anything smooth and fine is wrong. Get a navy blue blazer.
Shirts: light blue should be your staple. Again, can be worn with anything. Branch out with some blue/white patterned shirts (checks, stripes, etc.). Reserve other colors for when you have built up enough of a foundation and have mastered putting it to use. Reserve white shirts for business formal dress. Don't wear them with odd jackets.
Shoes: don't feel the need to buy many black pairs, though you should have one pair of black cap toes (punch caps if you like) for when you want to look the most business formal possible (to go with your white shirt). Instead, pick up many brown and burgundy shoes. In my opinion medium to dark brown, along with cordovan, are the the most versatile. Lighter browns and warmer chestnut-oriented hues can be very striking and beautiful, but are often harder to wear because they stand out more (they don't work well with dark grey suits, for example).
Done. More or less.