Men can match clothes way too easily, lol. My style is associated around the color of gray so everything matches simply.
Top-wear design: Simple one based design (striped or plaid or logo'd), heavy dark winter colors (dark olive green, dark maroon etc.) or pale colors (beige, light robin blue, etc.) associating either white or black outlines or just completely white, black or gray.
Bottom-wear design: Plain (pants) or plaid (shorts), dark colors (Gray, Black, Dark Blue etc.) or completely white.
Shoes: Think stripes (usually black or white).