A monochromatic color scheme is a great place to start. A charcoal colored button down shirt, black jeans, and a black sport coat create a classic look that most men can pull off well. Make sure your shirt-tails don't hang below your sport coat. If you decide to tuck in the shirt you have the opportunity to go flashier than normal with your belt (no studs or crazy stuff but push the envelope here a tad). If you want to rock the t-shirt, make sure it goes: a bright shirt will not work here. Instead try a black shirt with a muted design, or a high quality gray ribbed t-shirt.
If you go blue instead of black with the jacket, wear blue jeans and a white or cream colored button down. The t-shirt is not a great option here, but if you must, pick a cream with some texture or even a light brown. Also on the navy blazer you will want to avoid the golden buttons (unless you own a yacht and then go for it).
Mix in striped jackets, bold blazers, and other more aggressive options as you become more comfortable with the look.
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